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Journal articles on the topic 'Modification of the hyaluronic acid'

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Published: 28 June 2021

Last updated: 5 February 2022

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1

Lapčík, L., K. Benešová, L. Lapčík, S. De Smedt, and B. Lapčíková. "Chemical Modification of Hyaluronic Acid: Alkylation." International Journal of Polymer Analysis and Characterization 15, no. 8 (November 23, 2010): 486–96. http://dx.doi.org/10.1080/1023666x.2010.520904.

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2

Ponedel?kina, I. Yu, V. N. Odinokov, E. S. Vakhrusheva, M. T. Golikova, L. M. Khalilov, and U. M. Dzhemilev. "Modification of hyaluronic acid with aromatic amino acids." Russian Journal of Bioorganic Chemistry 31, no. 1 (January 2005): 82–86. http://dx.doi.org/10.1007/s11171-005-0011-y.

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3

Kuo, Jing Wen, David A. Swann, and Glenn D. Prestwich. "Chemical modification of hyaluronic acid by carbodiimides." Bioconjugate Chemistry 2, no. 4 (July 1991): 232–41. http://dx.doi.org/10.1021/bc00010a007.

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4

Zhang, Xin, Pengcheng Sun, Lingzi Huangshan, Bi-Huang Hu, and Phillip B. Messersmith. "Improved method for synthesis of cysteine modified hyaluronic acid for in situ hydrogel formation." Chemical Communications 51, no. 47 (2015): 9662–65. http://dx.doi.org/10.1039/c5cc02367j.

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5

Baker, Anna. "The evidence behind the biophysical properties of hyaluronic acid dermal fillers." Journal of Aesthetic Nursing 10, Sup1 (February 1, 2021): 39–42. http://dx.doi.org/10.12968/joan.2021.10.sup1.39.

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With the breadth and variety of hyaluronic acid hydrogels available, it can be challenging to understand the evolving product characteristics and associated terminology. Similarly, different hyaluronic acid hydrogels can share the same indication, and yet consist of different rheological and physiochemical properties. In this paper, hyaluronic acid biophysical properties, such as molecular weights, stabilisation (crosslinking), modification and hyaluronic acid concentration, are explored in relation to findings from current literature. The significance for these specific properties is explored in relation to specific indications and anti-ageing benefits.

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6

Laffleur, Flavia, Julia Röggla, Muneeb Ahmad Idrees, and Julia Griessinger. "Chemical Modification of Hyaluronic Acid for Intraoral Application." Journal of Pharmaceutical Sciences 103, no. 8 (August 2014): 2414–23. http://dx.doi.org/10.1002/jps.24060.

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7

Roberts, C. R., P. J. Roughley, and J. S. Mort. "Degradation of human proteoglycan aggregate induced by hydrogen peroxide. Protein fragmentation, amino acid modification and hyaluronic acid cleavage." Biochemical Journal 259, no. 3 (May 1, 1989): 805–11. http://dx.doi.org/10.1042/bj2590805.

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We have previously shown that treatment of neonatal human articular-cartilage proteoglycan aggregates with H2O2 results in loss of the ability of the proteoglycan subunits to interact with hyaluronic acid and in fragmentation of the link proteins [Roberts, Mort & Roughley (1987) Biochem. J. 247, 349-357]. We now show the following. (1) Hyaluronic acid in proteoglycan aggregates is also fragmented by treatment with H2O2. (2) Although H2O2 treatment results in loss of the ability of the proteoglycan subunits to interact with hyaluronic acid, the loss of this function is not attributable to substantial cleavage of the hyaluronic acid-binding region of the proteoglycan subunits. (3) In contrast, link proteins retain the ability to bind to hyaluronic acid following treatment with H2O2. (4) The interaction between the proteoglycan subunit and link protein is, however, abolished. (5) N-Terminal sequence analysis of the first eight residues of the major product of link protein resulting from H2O2 treatment revealed that cleavage occurred between residues 13 and 14, so that the new N-terminal amino acid is alanine. (6) In addition, a histidine (residue 16) is converted into alanine and an asparagine (residue 21) is converted into aspartate by the action of H2O2. (7) Rat link protein showed no cleavage or modifications in similar positions under identical conditions. (8) This species variation may be related to the different availability of histidine residues required for the co-ordination of the transition metal ion involved in hydroxyl-radical generation from H2O2. (9) Changes in function of these structural macromolecules as a result of the action of H2O2 may be consequences of both fragmentation and chemical modification.

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8

Santaella-Sosa, Erick. "Hyaluronic acid filler vascular complication management: an updated and easy-to-follow emergency protocol." Journal of Aesthetic Nursing 10, Sup1 (February 1, 2021): 34–38. http://dx.doi.org/10.12968/joan.2021.10.sup1.34.

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With the breadth and variety of hyaluronic acid hydrogels available, it can be challenging to understand the evolving product characteristics and associated terminology. Similarly, different hyaluronic acid hydrogels can share the same indication, and yet consist of different rheological and physiochemical properties. In this paper, hyaluronic acid biophysical properties, such as molecular weights, stabilisation (crosslinking), modification and hyaluronic acid concentration, are explored in relation to findings from current literature. The significance for these specific properties is explored in relation to specific indications and anti-ageing benefits.

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9

Lin, Quan Kui, Xiao Jie Huang, Jun Mei Tang, and Hao Chen. "Facile and Efficient Anti-Fouling Surface Construction on Poly(dimethylsiloxane) via Mussel-Inspired Chemistry." Advanced Materials Research 749 (August 2013): 344–49. http://dx.doi.org/10.4028/www.scientific.net/amr.749.344.

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Poly (dimethylsiloxane) (PDMS) silicones have found many applications in biomedical devices, such as catheters and intraocular lenses. But their hydrophobicity makes the possibility of the unexpected bioadhesion. In this paper, we reported a facile and efficient anti-fouling surface modification method on PDMS via self-polymerization of dopamine and the followed hyaluronic acid immobilization. Dopamine, commonly used as a neurotransmitter, is also a small molecule mimic of the adhesive proteins of mussels. Self-polymerization of dopamine can produce a thin polydopamine (PDA) layer on PDMS surface. Subsequently, thiol group functionalized hyaluronic acid (denoted as HA-SH) was immobilized covalently onto the resultant surface by the coupling between thiol group and reactive polydopamine layer. Then, the in vitro adhesion behaviors of the lens epithelial cells (LECs) and macrophage were investigated for evalution the anti-fouling effect of the hyaluronic acid modified PDMS surface. The results indicated that the cellular adhesion on PDMS were greatly decreased after hyaluronic acid modification, which suggested the potential application of such hyaluronic acid modified PDMS in biomedical applications.

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10

Kim, Jongho, Chaemyeong Lee, and Ji Hyun Ryu. "Adhesive Catechol-Conjugated Hyaluronic Acid for Biomedical Applications: A Mini Review." Applied Sciences 11, no. 1 (December 22, 2020): 21. http://dx.doi.org/10.3390/app11010021.

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Recently, catechol-containing polymers have been extensively developed as promising materials for surgical tissue adhesives, wound dressing, drug delivery depots, and tissue engineering scaffolds. Catechol conjugation to the polymer backbone provides adhesive properties to the tissue and does not significantly affect the intrinsic properties of the polymers. An example of a catecholic polymer is catechol-conjugated hyaluronic acid. In general, hyaluronic acid shows excellent biocompatibility and biodegradability; thus, it is used in various medical applications. However, hyaluronic acid alone has poor mechanical and tissue adhesion properties. Catechol modification considerably increases the mechanical and underwater adhesive properties of hyaluronic acid, while maintaining its biocompatibility and biodegradability and enabling its use in several biomedical applications. In this review, we briefly describe the synthesis and characteristics of catechol-modified hyaluronic acid, with a specific focus on catechol-involving reactions. Finally, we discuss the basic concepts and therapeutic effects of catechol-conjugated hyaluronic acid for biomedical applications.

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11

Liu, Yan, Huiyuan Hu, Xinlin Yang, Jing Lv, Li Zhou, and Zhongkuan Luo. "Hydrophilic modification on polyvinyl alcohol membrane by hyaluronic acid." Biomedical Materials 14, no. 5 (August 2, 2019): 055009. http://dx.doi.org/10.1088/1748-605x/ab3010.

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12

Holmes, M. W. A., M. T. Bayliss, and H. Muir. "Hyaluronic acid in human articular cartilage. Age-related changes in content and size." Biochemical Journal 250, no. 2 (March 1, 1988): 435–41. http://dx.doi.org/10.1042/bj2500435.

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Total tissue content and molecular mass of hyaluronic acid was determined in papain digests of human articular cartilage using a sensitive radiosorbent assay [Laurent & Tengblad (1980) Anal. Biochem. 109, 386-394]. 1) Hyaluronic acid content increased from 0.5 microgram/mg wet wt. to 2.5 micrograms/mg wet wt. between the ages of 2.5 years and 86 years. 2) Hyaluronic acid chain size decreased from Mr 2.0 x 10(6) to 3.0 x 10(5) over the same age range. 3) There was no age-related change in the size of newly-synthesized hyaluronic acid, which was of very high molecular mass, in both immature and mature cartilage. The results are consistent with an age-related decrease in proteoglycan aggregate size and suggest that modification of the hyaluronic acid chain may take place in the extracellular matrix.

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13

E. Salah, E. Salah, R. Ahmed R. Ahmed, E. Hala E. Hala, and B. Hala B. Hala. "Modification of Hyaluronic Acid with Hydrazine & Hydrazone; And Using their New Conjugates as Potential Antimicrobial Agents." Indian Journal of Applied Research 3, no. 7 (October 1, 2011): 23–26. http://dx.doi.org/10.15373/2249555x/july2013/8.

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14

Li, Hongru, Zhiping Qi, Shuang Zheng, Yuxin Chang, Weijian Kong, Chuan Fu, Ziyuan Yu, Xiaoyu Yang, and Su Pan. "The Application of Hyaluronic Acid-Based Hydrogels in Bone and Cartilage Tissue Engineering." Advances in Materials Science and Engineering 2019 (December 20, 2019): 1–12. http://dx.doi.org/10.1155/2019/3027303.

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At present, the healing of osteopathy, especially the healing of cartilage, has been proven to be difficult. Commonly used treatment methods are autogenous bone grafts and allogeneic bone grafts, but grafts cannot fully meet the clinical treatment requirements due to problems related to the source, price, immunity, and other concerns. Thus, the combination of biomaterials and tissue engineering technology has become a new direction in research. Among studies on tissue engineering bone and cartilage materials, hydrogels that show biological activity, absorbability after degradability, plasticity, and easy preparation have become the focus. Hydrogels are used as extracellular matrix mimics. Although various materials are able to form hydrogels, hyaluronic acid and its derivatives are prominently used. Hyaluronic acid hydrogels have many advantages, such as promoting cell adhesion and proliferation and wound healing. They also demonstrate sufficient biological activity for stimulating a microenvironment for cell survival. However, their disadvantages require further modification and include a poor degradation rate and insufficient mechanical performance. In this paper, hyaluronic acid-based hydrogels, their modifications, applications, and mechanisms, as well as new techniques for processing hyaluronic acid hydrogels in bone and cartilage tissue engineering, are briefly reviewed, and their future prospects and directions for future work are discussed.

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15

Ding, Yu Long, Hong Bo Zhang, Rui Xue Yin, and Wen Jun Zhang. "Photo-Crosslinkable Double-Network Hyaluronic Acid Based Hydrogel Dressing." Materials Science Forum 982 (March 2020): 59–66. http://dx.doi.org/10.4028/www.scientific.net/msf.982.59.

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Hyaluronic acid (HA)-based hydrogels are widely used in biomedical applications due to their excellent biocompatibility and enzymatic degradability. In this paper a photo-crosslinking double-network hyaluronic acid-based hydrogel dressing was proposed. Hyaluronic acid can be UV-crosslinked by modification with methacrylic anhydride (HA-MA) and disulfide-crosslinked by modification with 3,3'-dithiobis (propionylhydrazide) (DTP) (HA-SH). The mixings of these two materials at different ratios were produced. All the samples can be quickly gelled at 365 nm for 10 s. The rheological tests show that the storage modulus (G') of the double network (HA-SH/HA-MA) hydrogel is increased with the increase of HA-SH content. The HA-SH/HA-MA hydrogel has porous structure, high swelling ratio and Controlled degradation rate. In vitro degradation tests show that the ratio of HA-SH/HA-MA ratio was 9:1 (S9M1) in 100 U/ml hyaluronidase (Hase) degraded by 89.91±2.26% at 11d. The cytocompatibility of HA-SH/HA-MA hydrogels was proved by Live/Dead stainings and CCK-8 assays in the human dermis fibroblasts (HDF) cells test. All these results highlight the biological potential of the HA-SH/HA-MA hydrogels for DFU intervention.

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16

Ikeda, Jun, Chunfeng Zhao, Yu-Long Sun, Kai-Nan An, and Peter C. Amadio. "Carbodiimide-Derivatized Hyaluronic Acid Surface Modification of Lyophilized Flexor Tendon." Journal of Bone & Joint Surgery 92, no. 2 (February 2010): 388–95. http://dx.doi.org/10.2106/jbjs.h.01641.

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17

Collins, Maurice N., and Colin Birkinshaw. "Hyaluronic acid solutions-A processing method for efficient chemical modification." Journal of Applied Polymer Science 130, no. 1 (March 8, 2013): 145–52. http://dx.doi.org/10.1002/app.39145.

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18

Oh, Eun Ju, Ji Seok Kim, and Sei Kwang Hahn. "A Novel Degradation Controlled Hyaluronic Acid Derivatives." Key Engineering Materials 342-343 (July 2007): 525–28. http://dx.doi.org/10.4028/www.scientific.net/kem.342-343.525.

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A novel protocol to control the molecular degradation of hyaluronic acid (HA) was successfully developed. HA has a different conformational structure in water and in organic solvent, and the carboxyl group of HA is known to be the recognition site of CD44 and hyaluronidase. Based on these facts, HA was chemically modified in the mixed solvent of water and ethanol by grafting adipic acid dihydrazide (ADH) to the carboxyl group of HA, which resulted in high degree of ADH modification up to 85 mol% with controlled degradation of HA by hyaluronidase. The degradation controlled HA-ADH will be assessed for various tissue engineering applications.

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19

Московцев, А. А., Д. М. Зайченко, В. Н. Хабаров, Н. П. Михайлова, Д. Ю. Тявин, М. А. Селянин, А. А. Соколовская, and А. А. Кубатиев. "A new composition of hyaluronic acid modifications, HR-2, with proteinogenic amino acids increases the metabolic activity of fibroblasts without pronounced proliferative effects." Nauchno-prakticheskii zhurnal «Patogenez», no. 4() (December 11, 2018): 28–36. http://dx.doi.org/10.25557/2310-0435.2018.04.28-36.

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Гетерополисахарид гиалуронан, являясь ключевым компонентом внеклеточного матрикса, играет важную роль в поддержании определенных физико-химических условий в тканях. Кроме того, гиалуронан может модулировать состояние клеток через взаимодействие с рецепторами и эндоцитоз, однако, эти эффекты недостаточно изучены. Благодаря своим уникальным свойствам, гиалуронан нашел широкое применение в разных областях биомедицины, в частности, активно используется в качестве микроимплантатов в дерму для коррекции возрастных изменений кожи. Вместе с тем, нативный гиалуронан нестабилен при инъекции и подвергается быстрой деградации в ткани, что существенно ограничивает продолжительность вызываемых им эффектов. В данной работе исследуется новая композиция на основе гиалуронана - HR-2, которую отличают ковалентные сшивки между цепями, введенные путем разработанной авторами одностадийной технологии твердофазной модификации полисахаридов. Сшивки препятствуют быстрой деградации гиалуронана. Авторами предложена концепция функционирования гиалуронана в ткани в качестве депо протеиногенных аминокислот и витаминов в целях поддержания биосинтетической активности клеток. Ранее было показано, что сшитый по данной технологии гиалуронан более стабилен в дерме, в связи с чем его действие в качестве депо может быть пролонгировано. В данной работе исследуется влияние на эндотелиоцитоподобные клетки и фибробласты препарата HR-2, представляющего собой новую композицию гиалуроната натрия и сополимера гиалуроновой кислоты с аскорбилфосфатом магния с добавлением глицина, пролина, лизина. В работе проводится сравнение с немодифицированным гиалуронатом натрия. Установлено, что композиция HR-2 в сравнительно высоких концентрациях дозозависимо увеличивает активность дегидрогеназ в фибробластах, что может свидетельствовать о метаболическом их стимулировании. Это отличает препарат HR-2 от нативной гиалуроновой кислоты, ингибирующей в этих же концентрациях метаболическую активность фибробластов. Оба препарата - и HR-2, и нативная гиалуроновая кислота - в малых концентрациях вызывают гормезис-подобный, стимулирующий метаболизм эндотелиоцитов эффект. Цитотоксичность композиции HR-2 ниже нативной гиалуроновой кислоты на обоих клеточных типах. Следует также отметить, что не выявлено достоверного пролиферативного действия обоих препаратов. Полученные в работе новые сведения могут быть использованы для оптимизации режимов применения препаратов гиалуроновой кислоты в биомедицине, с целью достижения максимального терапевтического эффекта и снижения нежелательных последствий его применения. Hyaluronan (HA) is a linear heteropolysaccharide, a key component of the extracellular matrix. It plays an important role in maintaining certain physicochemical conditions in tissues. In addition, hyaluronan can modulate the state of cells through interaction with receptors and endocytosis; however, these effects are not well understood. Due to its unique properties, hyaluronan is widely used in various fields of biomedicine, in particular, as microimplant for correction of age-related skin changes. However, native hyaluronan is unstable when injected and undergoes rapid degradation in the tissue, which significantly limits duration of its effects. In this study, we evaluated a new hyaluronan-based composition, HR-2, which is distinguished by covalent cross-links between the chains. Those cross-links were incorporated using a one-stage technology of solid-phase modification of polysaccharides developed by the authors. The cross-links prevent the rapid degradation of hyaluronan. The authors proposed a concept of injecting hyaluronan into tissue as a depot of proteinogenic amino acids and vitamins in order to maintain the biosynthetic activity of cells. Previously it was shown that hyaluronan produced with this technology was more stable in the dermis, and, therefore, its performance as a depot can be prolonged. In this work, we studied the effect on endotheliocyte-like cells and fibroblasts of HR-2, which is a new composition of sodium hyaluronate and a copolymer of hyaluronic acid with magnesium ascorbyl phosphate supplemented with glycine, proline, and lysine. The study compared HR-2 with unmodified sodium hyaluronate. We found that the composition of HR-2 in relatively high concentrations dose-dependently increased dehydrogenase activities in fibroblasts, that might indicate their metabolic stimulation. This differs HR-2 from native hyaluronic acid, which inhibits the metabolic activity of fibroblasts when added in similar concentrations. Low concentrations of both drugs, HR-2 and native hyaluronic acid, exerted a hormesis-like effect on endotheliocyte metabolism. Cytotoxicity of the HR-2 formulation was lower than of native hyaluronic acid in both cell types. It should also be noted that no reliable proliferative effects of both drugs have been identified. The new information obtained in this study can help optimizing the use of hyaluronic acid drugs in biomedicine to achieve the best therapeutic effect and reduce undesirable consequences of its use.

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Dadoo, Nayereh, and William M. Gramlich. "Spatiotemporal Modification of Stimuli-Responsive Hyaluronic Acid/Poly(N-isopropylacrylamide) Hydrogels." ACS Biomaterials Science & Engineering 2, no. 8 (July 6, 2016): 1341–50. http://dx.doi.org/10.1021/acsbiomaterials.6b00259.

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21

Sochilina, A. V., A. G. Savelyev, P. A. Demina, N. V. Ierusalimsky, D. A. Khochenkov, R. A. Akasov, N. V. Sholina, E. V. Khaydukov, and A. N. Generalova. "Controlled modification of hyaluronic acid for photoinduced reactions in tissue engineering." Journal of Physics: Conference Series 1124 (December 2018): 031014. http://dx.doi.org/10.1088/1742-6596/1124/3/031014.

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22

Momose, Toshimitsu, Peter C. Amadio, Yu-Long Sun, Chunfeng Zhao, Mark E. Zobitz, Jeffrey R. Harrington, and Kai-Nan An. "Surface modification of extrasynovial tendon by chemically modified hyaluronic acid coating." Journal of Biomedical Materials Research 59, no. 2 (November 2, 2001): 219–24. http://dx.doi.org/10.1002/jbm.1235.

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23

Lee, Sanghun, Semin Kim, Junggeon Park, and Jae Young Lee. "Universal surface modification using dopamine-hyaluronic acid conjugates for anti-biofouling." International Journal of Biological Macromolecules 151 (May 2020): 1314–21. http://dx.doi.org/10.1016/j.ijbiomac.2019.10.177.

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24

Li, Yuqing, Yongtai Zheng, Xinyi Lai, Yuehuan Chu, and Yongming Chen. "Biocompatible surface modification of nano-scale zeolitic imidazolate frameworks for enhanced drug delivery." RSC Advances 8, no. 42 (2018): 23623–28. http://dx.doi.org/10.1039/c8ra03616k.

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25

Zagorulko, Y. Y., and E. Y. Zagorulko. "Features of Hyaluronic Acid Solutions for Intra-articular Introduction and Recent Trends in Their Development (Review)." Drug development & registration 9, no. 2 (May 30, 2020): 45–54. http://dx.doi.org/10.33380/2305-2066-2020-9-2-45-54.

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Introduction. The most common way to maintain the viscoelastic properties of synovial fluid is intra-articular administration of hyaluronic acid solutions. Such forms have several features due to the method of administration, the characteristics of the substance, as well as their composition, technology, and packaging. The aim of the work to analyze the features of hyaluronic acid solutions for intra-articular administration, as well as to consider resent trends to their pharmaceutical development.Text. Currently, in Russia, most of these forms are registered as medical devices. Each drug has its characteristics, including the source of the substance, the main molecular weight and the molecular weight range of hyaluronic acid, the structure of the molecule (linear or cross-linked), the method of its chemical modification, concentration, solution volume, dosage, etc. As excipients most often use sodium chloride, water for injection, and phosphate-buffered saline to maintain pH values close to the synovial fluid. Some prostheses contain mannitol as an antioxidant. Combinations of hyaluronic acid with active chondroprotective substances (chondroitin sulfate, sodium succinate) are known. The main type of primary packaging is glass prefilled syringes. The choice of sterilization methods is determined by the chemical structure of hyaluronic acid, aseptic production is used for most prostheses.Conclusion. Currently, research solutions to create thermostable and enzyme-resistant compositions with hyaluronic acid for intra-articular administration are being successfully applied. Modern developments are aimed at creating polymer complexes of hyaluronic acid with substances that improve the lubricity of solutions, the development of nanosystems (liposomes, nanoparticles, nano micelles, etc.) with chondroprotective, as well as the creation of inert biocompatible prostheses with viscoelastic properties. The creation of forms of hyaluronic acid and alternative drugs that can support the rheological properties of synovial fluid is currently a promising area of research.

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26

Lee, J. Y., Z. Z. Khaing, J. J. Siegel, and C. E. Schmidt. "Surface modification of neural electrodes with a pyrrole-hyaluronic acid conjugate to attenuate reactive astrogliosis in vivo." RSC Advances 5, no. 49 (2015): 39228–31. http://dx.doi.org/10.1039/c5ra03294f.

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27

Mattioli-Belmonte, M., F. Gabbanelli, T. Casoli, A. Delfino, F. Giantomassi, G. Biagini, G. Giavaresi, P. Torricelli, and M. Fini. "Fabricated HyalS Micropatterns and Surface Guidance of NCTC 2544 Continuous Cell Line: An in Vitro Study." International Journal of Artificial Organs 25, no. 9 (September 2002): 892–98. http://dx.doi.org/10.1177/039139880202500912.

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Surface topography is important in establishing tissue organisation adjacent to implants, smooth surfaces generally being associated with fibrous encapsulation. By virtue of its large hydrated molecular volume and its capacity to form molecular matrix, hyaluronic acid can expand the interfibrillar collagen spaces to allow the movement of cells, although it can also hamper their locomotion. Low molecular-weight hyaluronan can also stimulate cell proliferation, especially at low concentrations. The aim of the present work was to evaluate in vitro the growth and migratory behaviour of NCTC 2544 keratinocytes cultured on different materials microstructured with hyaluronic acid or sulfated hyaluronic acid to assess the possibility of using these devices in the repair process of soft tissues. Ultrastructural morphological analyses, morphometric evaluations and detection of cytoskeletal elements were performed. Our observations provide evidence that micrometer-size parallel grooves of hyaluronic acid can influence cell growth behaviour since cells seeded onto the microstructured substrate arranged themselves according to a shape and an orientation that clearly reflected the chemotropism exerted on them by the two forms of acid. These data also highlight the importance of accurate microtexture fabrication. We intend to follow up these in vitro studies with in vivo experimental applications using PET and gelatin substrates structured with HyalS to evaluate wound healing responses, and to extend our investigations of the cytoskeletal modifications induced by different microstructures.

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28

Kim, Choi, Choi, Park, and Ryu. "Hyaluronic Acid-Coated Nanomedicine for Targeted Cancer Therapy." Pharmaceutics 11, no. 7 (June 30, 2019): 301. http://dx.doi.org/10.3390/pharmaceutics11070301.

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Hyaluronic acid (HA) has been widely investigated in cancer therapy due to its excellent characteristics. HA, which is a linear anionic polymer, has biocompatibility, biodegradability, non-immunogenicity, non-inflammatory, and non-toxicity properties. Various HA nanomedicines (i.e., micelles, nanogels, and nanoparticles) can be prepared easily using assembly and modification of its functional groups such as carboxy, hydroxy and N-acetyl groups. Nanometer-sized HA nanomedicines can selectively deliver drugs or other molecules into tumor sites via their enhanced permeability and retention (EPR) effect. In addition, HA can interact with overexpressed receptors in cancer cells such as cluster determinant 44 (CD44) and receptor for HA-mediated motility (RHAMM) and be degraded by a family of enzymes called hyaluronidase (HAdase) to release drugs or molecules. By interaction with receptors or degradation by enzymes inside cancer cells, HA nanomedicines allow enhanced targeting cancer therapy. In this article, recent studies about HA nanomedicines in drug delivery systems, photothermal therapy, photodynamic therapy, diagnostics (because of the high biocompatibility), colloidal stability, and cancer targeting are reviewed for strategies using micelles, nanogels, and inorganic nanoparticles.

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Vil’danova, R. R., N. N. Sigaeva, O. S. Kukovinets, V. P. Volodina, L. V. Spirikhin, I. S. Zaidullin, and S. V. Kolesov. "Modification of hyaluronic acid and chitosan, aimed at developing hydrogels for ophthalmology." Russian Journal of Applied Chemistry 87, no. 10 (October 2014): 1547–57. http://dx.doi.org/10.1134/s1070427214100231.

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Payne, William M., Denis Svechkarev, Alexander Kyrychenko, and Aaron M. Mohs. "The role of hydrophobic modification on hyaluronic acid dynamics and self-assembly." Carbohydrate Polymers 182 (February 2018): 132–41. http://dx.doi.org/10.1016/j.carbpol.2017.10.054.

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Sabino, Marcos Antonio, Maria Gabriela Carrero, and Carlos Julio Rodriguez. "Intelligent copolymers based on poly (N-isopropilacrylamide). Part ii: Grafts polysaccharide to obtain new biomaterials for biomedical and pharmacological applications." International Journal of Advances in Medical Biotechnology - IJAMB 2, no. 1 (March 1, 2019): 17. http://dx.doi.org/10.25061/2595-3931/ijamb/2019.v2i1.31.

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Biopolymers such as polysaccharides are compounds that have functional groups and they are very susceptible to be used in chemical modifications and also allows them to synthesizer of new copolymers (used as graft-like chains). Poly (N-Isopropylacrylamide) PNIPAm, is a thermosensitive synthetic polymer widely used in the preparation of intelligent gels for the biomedical field, but have some limitations in use as biodegradable matrix or scaffolds. In this research wered the synthesis and characterization of copolymers their PNIPAm grafted with the polysaccharides: chitosan (CS) or hyaluronic acid (HA), were performed to obtain new biodegradable and biocompatible biomaterials that conserve the intelligent character (thermosensitivity).The PNIPAm was in first chemically modified with 3-butenoic acid in order to generate carboxyl end groups on the graft-polymer chain (PNIPAm-co-COOH) which serve as anchor points and then covalently graft the polysaccharides. For the specific case of grafting with hyaluronic acid, it was necessary to perform a second modification using piperazine (PIP) and obtain the graft-polymers PNIPAm-co-COO-g-PIP. All this modification process was previously reported (Carrero et al, 2018). In this case, the polysaccharides used as grafts-like chains were: (1) chitosan oligomers obtained by acid degradation and (2) hyaluronic acid. The characterization of all copolymers obtained was follow by infrared spectroscopic (FT-IR); the differential scanning calorimetric (DSC) technique was used to determine the lower critical solution transition temperature (LCST), resulting in the range of 29-34 °C. Its morphology was studied using scanning electron microscopy (SEM), but previously was simulate an inject process, for the reversible gel character presented by these novel copolymers; resulting a high porosity and interconnection between pores (scaffold-like micrometric structures). Hemocompatibility assays were performed on agar/blood systems, showing non cytotoxicity. All these results give these graftcopolymers a high potentiality of use as scaffolds in tissue engineering and also for pharmacological applications.

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Egle, Karina, and Arita Dubnika. "Development of Bioadhesive Biomaterials Based on Silk and Hyaluronic Acid." Key Engineering Materials 850 (June 2020): 236–41. http://dx.doi.org/10.4028/www.scientific.net/kem.850.236.

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Silk fibroin can be derived from the silkworm Bombyx mori and it has the main properties for its use as bioadhesive biomaterial in medicine – biocompatibility, good mechanical properties and controllable degradation rate. On the other hand hyaluronic acid (HA) is an attractive polymer for biomedical applications, due to its biological and structural importance, as well as its ease of modification. Thus in this study, two types of silk raw materials for preparation of silk fibroin (SF) solutions were used. Obtained SF solutions with and without hyaluronic acid (HA) were cross-linked to form hydrogels. Widely used cross-linking agent glutaraldehyde (GTA) was used in this study. Two temperatures 37°C and 60°C were chosen to determine the effect of temperature on the cross-linking rate of the samples. The gelation time, swelling ratio and structural features of the adhesive were also studied.

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Abatangelo, G., V. Vindigni, G. Avruscio, L. Pandis, and P. Brun. "Hyaluronic Acid: Redefining Its Role." Cells 9, no. 7 (July 21, 2020): 1743. http://dx.doi.org/10.3390/cells9071743.

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The discovery of several unexpected complex biological roles of hyaluronic acid (HA) has promoted new research impetus for biologists and, the clinical interest in several fields of medicine, such as ophthalmology, articular pathologies, cutaneous repair, skin remodeling, vascular prosthesis, adipose tissue engineering, nerve reconstruction and cancer therapy. In addition, the great potential of HA in medicine has stimulated the interest of pharmaceutical companies which, by means of new technologies can produce HA and several new derivatives in order to increase both the residence time in a variety of human tissues and the anti-inflammatory properties. Minor chemical modifications of the molecule, such as the esterification with benzyl alcohol (Hyaff-11® biomaterials), have made possible the production of water-insoluble polymers that have been manufactured in various forms: membranes, gauzes, nonwoven meshes, gels, tubes. All these biomaterials are used as wound-covering, anti-adhesive devices and as scaffolds for tissue engineering, such as epidermis, dermis, micro-vascularized skin, cartilage and bone. In this review, the essential biological functions of HA and the applications of its derivatives for pharmaceutical and tissue regeneration purposes are reviewed.

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Perez-Rizquez, Carlos, David Lopez-Tejedor, Laura Plaza-Vinuesa, Blanca de las Rivas, Rosario Muñoz, Jose Cumella, and Jose M. Palomo. "Chemical Modification of Novel Glycosidases from Lactobacillus plantarum Using Hyaluronic Acid: Effects on High Specificity against 6-Phosphate Glucopyranoside." Coatings 9, no. 5 (May 9, 2019): 311. http://dx.doi.org/10.3390/coatings9050311.

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Three novel glycosidases produced from Lactobacillus plantarum, so called Lp_0440, Lp_2777, and Lp_3525, were isolated and overexpressed on Escherichia coli containing a His-tag for specific purification. Their specific activity was evaluated against the hydrolysis of p-nitrophenylglycosides and p-nitrophenyl-6-phosphate glycosides (glucose and galactose) at pH 7. All three were modified with hyaluronic acid (HA) following two strategies: A simple coating by direct incubation at alkaline pH or direct chemical modification at pH 6.8 through preactivation of HA with carbodiimide (EDC) and N-hydroxysuccinimide (NHS) at pH 4.8. The modifications exhibited important effect on enzyme activity and specificity against different glycopyranosides in the three cases. Physical modification showed a radical decrease in specific activity on all glycosidases, without any significant change in enzyme specificity toward monosaccharide (glucose or galactose) or glycoside (C-6 position free or phosphorylated). However, the surface covalent modification of the enzymes showed very interesting results. The glycosidase Lp_0440 showed low glycoside specificity at 25 °C, showing the same activity against p-nitrophenyl-glucopyranoside (pNP-Glu) or p-nitrophenyl-6-phosphate glucopyranoside (pNP-6P-Glu). However, the conjugated cHA-Lp_0440 showed a clear increase in the specificity towards the pNP-Glu and no activity against pNP-6P-Glu. The other two glycosidases (Lp_2777 and Lp_3525) showed high specificity towards pNP-6P-glycosides, especially to the glucose derivative. The HA covalent modification of Lp_3525 (cHA-Lp_3525) generated an enzyme completely specific against the pNP-6P-Glu (phosphoglycosidase) maintaining more than 80% of the activity after chemical modification. When the temperature was increased, an alteration of selectivity was observed. Lp_0440 and cHA-Lp_0440 only showed activity against p-nitrophenyl-galactopyranoside (pNP-Gal) at 40 °C, higher than at 25 °C in the case of the conjugated enzyme.

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Lim, Hyun Ju, T. Hiran Perera, Thomas S. Wilems, Sukhen Ghosh, Yi-Yan Zheng, Ali Azhdarinia, Qilin Cao, and Laura A. Smith Callahan. "Response to di-functionalized hyaluronic acid with orthogonal chemistry grafting at independent modification sites in rodent models of neural differentiation and spinal cord injury." Journal of Materials Chemistry B 4, no. 42 (2016): 6865–75. http://dx.doi.org/10.1039/c6tb01906d.

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Prestwich, Glenn D., Dale M. Marecak, James F. Marecek, Koen P. Vercruysse, and Michael R. Ziebell. "Controlled chemical modification of hyaluronic acid: synthesis, applications, and biodegradation of hydrazide derivatives." Journal of Controlled Release 53, no. 1-3 (April 1998): 93–103. http://dx.doi.org/10.1016/s0168-3659(97)00242-3.

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37

Kenne, Lennart, Suresh Gohil, Eva M. Nilsson, Anders Karlsson, David Ericsson, Anne Helander Kenne, and Lars I. Nord. "Modification and cross-linking parameters in hyaluronic acid hydrogels—Definitions and analytical methods." Carbohydrate Polymers 91, no. 1 (January 2013): 410–18. http://dx.doi.org/10.1016/j.carbpol.2012.08.066.

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38

Yang, Biao, Xueping Guo, Hengchang Zang, and Jianjian Liu. "Determination of modification degree in BDDE-modified hyaluronic acid hydrogel by SEC/MS." Carbohydrate Polymers 131 (October 2015): 233–39. http://dx.doi.org/10.1016/j.carbpol.2015.05.050.

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39

Zhang, Ling, Yumei Xiao, Bo Jiang, Hongsong Fan, and Xingdong Zhang. "Effect of adipic dihydrazide modification on the performance of collagen/hyaluronic acid scaffold." Journal of Biomedical Materials Research Part B: Applied Biomaterials 9999B (2009): NA. http://dx.doi.org/10.1002/jbm.b.31516.

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40

Sikkema, Rebecca, Blanca Keohan, and Igor Zhitomirsky. "Hyaluronic-Acid-Based Organic-Inorganic Composites for Biomedical Applications." Materials 14, no. 17 (August 31, 2021): 4982. http://dx.doi.org/10.3390/ma14174982.

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Applications of natural hyaluronic acid (HYH) for the fabrication of organic-inorganic composites for biomedical applications are described. Such composites combine unique functional properties of HYH with functional properties of hydroxyapatite, various bioceramics, bioglass, biocements, metal nanoparticles, and quantum dots. Functional properties of advanced composite gels, scaffold materials, cements, particles, films, and coatings are described. Benefiting from the synergy of properties of HYH and inorganic components, advanced composites provide a platform for the development of new drug delivery materials. Many advanced properties of composites are attributed to the ability of HYH to promote biomineralization. Properties of HYH are a key factor for the development of colloidal and electrochemical methods for the fabrication of films and protective coatings for surface modification of biomedical implants and the development of advanced biosensors. Overcoming limitations of traditional materials, HYH is used as a biocompatible capping, dispersing, and structure-directing agent for the synthesis of functional inorganic materials and composites. Gel-forming properties of HYH enable a facile and straightforward approach to the fabrication of antimicrobial materials in different forms. Of particular interest are applications of HYH for the fabrication of biosensors. This review summarizes manufacturing strategies and mechanisms and outlines future trends in the development of functional biocomposites.

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Sun, Yulong, Chunfeng Zhao, Peter C. Amadio, and Kai-Nan An. "Biomimetic modification of the gliding surface of extrasynovial tendon." Journal of Materials Research 21, no. 8 (August 1, 2006): 2079–83. http://dx.doi.org/10.1557/jmr.2006.0253.

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Tendons may be classified as intrasynovial or extrasynovial based upon their anatomic location. We studied the physical properties of extrasynovial and intrasynovial tendons. Extrasynovial tendon has a rougher surface and higher friction than intrasynovial tendon. A number of carbodiimide derivatized biomaterials were developed to modify the irregular surface of an extrasynovial tendon to mimic the smooth surface of an intrasynovial tendon. We found that carbodiimide derivatized hyaluronic acid-gelatin (cd-HA-gelatin) chemically bonded to the extrasynovial tendon surface and optimally reduced gliding resistance in vitro. This biosynthetic, biomimetic modification of the extrasynovial tendon surface may prove to be a useful clinical product.

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Si, Xing, Ding, Zhang, Yin, and Zhang. "3D Bioprinting of the Sustained Drug Release Wound Dressing with Double-Crosslinked Hyaluronic-Acid-Based Hydrogels." Polymers 11, no. 10 (September 27, 2019): 1584. http://dx.doi.org/10.3390/polym11101584.

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：Hyaluronic acid (HA)-based hydrogels are widely used in biomedical applications due to their excellent biocompatibility. HA can be Ultraviolet (UV)-crosslinked by modification with methacrylic anhydride (HA-MA) and crosslinked by modification with 3,3'-dithiobis(propionylhydrazide) (DTP) (HA-SH) via click reaction. In the study presented in this paper, a 3D-bioprinted, double-crosslinked, hyaluronic-acid-based hydrogel for wound dressing was proposed. The hydrogel was produced by mixing HA-MA and HA-SH at different weight ratios. The rheological test showed that the storage modulus (G') of the HA-SH/HA-MA hydrogel increased with the increase in the HA-MA content. The hydrogel had a high swelling ratio and a high controlled degradation rate. The in vitro degradation test showed that the hydrogel at the HA-SH/HA-MA ratio of 9:1 (S9M1) degraded by 89.91% ± 2.26% at 11 days. The rheological performance, drug release profile and the cytocompatibility of HA-SH/HA-MA hydrogels with loaded Nafcillin, which is an antibacterial drug, were evaluated. The wound dressing function of this hydrogel was evaluated by Live/Dead staining and CCK-8 assays. The foregoing results imply that the proposed HA-SH/HA-MA hydrogel has promise in wound repair applications.

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Hsieh, Cindy Yi Chi, Fang-Wei Hu, Wen-Shiang Chen, and Wei-Bor Tsai. "Reducing the Foreign Body Reaction by Surface Modification with Collagen/Hyaluronic Acid Multilayered Films." ISRN Biomaterials 2014 (April 13, 2014): 1–8. http://dx.doi.org/10.1155/2014/718432.

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Biological response against foreign implants often leads to encapsulation, possibly resulting in malfunction of implants devices. The aim of this study was to reduce the foreign body reaction by surface modification of biomaterials through layer-by-layer deposition of type I collagen (COL)/hyaluronic acid (HA) multilayer films. Polydimethylsiloxane (PDMS) samples were coated with alternative COL and HA layers with different layers. We found that the in vitro adhesion, proliferation, and activation of macrophage-like cells were greatly decreased by COL/HA multilayered deposition. The PDMS samples modified with 20 bilayers of COL/HA were implanted in rats for 3 weeks, and the thickness of encapsulation surrounding the samples was decreased by 29–57% compared to the control unmodified PDMS. This study demonstrates the potential of COL/HA multilayer films to reduce foreign body reaction.

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Chen, Hao, Xuhong Chen, Huiying Chen, Xin Liu, Junxing Li, Jun Luo, Aihua He, Charles C. Han, Ying Liu, and Shanshan Xu. "Molecular Interaction, Chain Conformation, and Rheological Modification during Electrospinning of Hyaluronic Acid Aqueous Solution." Membranes 10, no. 9 (August 31, 2020): 217. http://dx.doi.org/10.3390/membranes10090217.

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Most of natural water-soluble polymers are difficult to electrospin due to their specific chain conformation in aqueous solution, which limits their applications. This study investigated the effects of polyethylene oxide (PEO) on the electrospinning of hyaluronic acid (HA) in HA/PEO aqueous solutions. The rheological properties of HA/PEO aqueous solutions showed polymer chain entanglement in HA was the essential factor affecting its electrospinnability. Wide-angle X-ray scattering and differential scanning calorimetry analyses of a PEO crystal showed different crystallization behavior of the PEO chain with different molecular weight, which indicates different interaction with HA. A schematic molecular model has been proposed to explain the effect of PEO on the chain conformation of HA along with the relationship between electrospinnability and chain entanglement. PEO with a relatively high molecular weight with limited crystal formation formed extensive chain entanglements with HA, while PEO with relatively low molecular weight weakened the interactions among HA chains. The findings of this study provide a wide perspective to better understand the electrospinning mechanisms of natural polyelectrolytes and usage in tissue engineering.

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Wang, Xiaoying, Yamin Li, Quanshun Li, Caleb I. Neufeld, Dimitra Pouli, Shuo Sun, Liu Yang, et al. "Hyaluronic acid modification of RNase A and its intracellular delivery using lipid-like nanoparticles." Journal of Controlled Release 263 (October 2017): 39–45. http://dx.doi.org/10.1016/j.jconrel.2017.01.037.

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46

PRESTWICH, G. D., D. M. MARECAK, J. F. MARECEK, K. P. VERCRUYSSE, and M. R. ZIEBELL. "ChemInform Abstract: Chemical Modification of Hyaluronic Acid for Drug Delivery, Biomaterials and Biochemical Probes." ChemInform 29, no. 46 (June 19, 2010): no. http://dx.doi.org/10.1002/chin.199846316.

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Lih, Eugene, So Yoon Chi, Tae Il Son, Yoon Ki Joung, and Dong Keun Han. "Facile Surface Modification of Nitinol with Dopamine-Conjugated Hyaluronic Acid for Improving Blood Compatibility." Journal of Biomaterials and Tissue Engineering 6, no. 10 (October 1, 2016): 780–87. http://dx.doi.org/10.1166/jbt.2016.1507.

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48

Guidi, Giuliano, Myrto Korogiannaki, and Heather Sheardown. "Modification of Timolol Release From Silicone Hydrogel Model Contact Lens Materials Using Hyaluronic Acid." Eye & Contact Lens: Science & Clinical Practice 40, no. 5 (September 2014): 269–76. http://dx.doi.org/10.1097/icl.0000000000000033.

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49

Chahuki, Fatemeh Fotouhi, Saeed Aminzadeh, Vahab Jafarian, Fatemeh Tabandeh, and Mahvash Khodabandeh. "Hyaluronic acid production enhancement via genetically modification and culture medium optimization in Lactobacillus acidophilus." International Journal of Biological Macromolecules 121 (January 2019): 870–81. http://dx.doi.org/10.1016/j.ijbiomac.2018.10.112.

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Kwon, Mi Y., Chao Wang, Jonathan H. Galarraga, Ellen Puré, Lin Han, and Jason A. Burdick. "Influence of hyaluronic acid modification on CD44 binding towards the design of hydrogel biomaterials." Biomaterials 222 (November 2019): 119451. http://dx.doi.org/10.1016/j.biomaterials.2019.119451.

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