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Journal articles on the topic 'Cyanines and squaraines'

Author: Grafiati

Published: 25 May 2024

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1

Dereje, Degnet Melese, Carlotta Pontremoli, Maria Jesus Moran Plata, Sonja Visentin, and Nadia Barbero. "Polymethine dyes for PDT: recent advances and perspectives to drive future applications." Photochemical & Photobiological Sciences 21, no. 3 (February 1, 2022): 397–419. http://dx.doi.org/10.1007/s43630-022-00175-6.

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AbstractIt has been proved that the effectiveness of photodynamic therapy (PDT) is closely related to the intrinsic features of the photosensitizer (PS). Over the recent years, several efforts have been devoted to the discovery of novel and more efficient photosensitizers showing higher efficacy and lower side effects. In this context, squaraine and cyanine dyes have been reported to potentially overcome the drawbacks related to the traditional PSs. In fact, squaraines and cyanines are characterized by sharp and intense absorption bands and narrow emission bands with high extinction coefficients typically in the red and near-infrared region, good photo and thermal stability and a strong fluorescent emission in organic solvents. In addition, biocompatibility and low toxicity make them suitable for biological applications. Despite these interesting intrinsic features, their chemical instability and self-aggregation properties in biological media still limit their use in PDT. To overcome these drawbacks, the self-assembly and incorporation into smart nanoparticle systems are forwarded promising approaches that can control their physicochemical properties, providing rational solutions for the limitation of free dye administration in the PDT application. The present review summarizes the latest advances in squaraine and cyanine dyes for PDT application, analyzing the different strategies, i.e.the self-assembly and the incorporation into nanoparticles, to further enhance their photochemical properties and therapeutic potential. The in vivo assessments are still limited, thus further delaying their effective application in PDT. Graphical abstract

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2

Dülcks, Thomas, Walter Grahn, Hans-Hermann Johannes, Ulf Lawrentz, Miriam Rittner, Hans-Martin Schiebel, and Peter Schulze. "Mass Spectrometry of Oligomeric Cyanines and Squaraines of the Indole Series: Fast Atom Bombardment-Induced Chemical Reactions." Zeitschrift für Naturforschung B 57, no. 4 (April 1, 2002): 393–98. http://dx.doi.org/10.1515/znb-2002-0405.

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Fast atom bombardment (FAB) has been used for mass spectrometric characterization of oligomeric cyanines and squaraines of the indole series which are linked by different aromatic spacers. Markedly different results were obtained for the oligomers and for the corresponding monomers. In addition to the expected mono-anions and mono-cations, ions of high relative abundance were detected which can only be explained on the basis of FAB-induced chemical reactions of the initial oligomers. Formation of allenes, hydrogenation and dehydrogenation, respectively, is characteristic for this class of compounds under FAB-conditions.

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3

Lima, Eurico, Renato E. Boto, Diana Ferreira, José R. Fernandes, Paulo Almeida, Luis F. V. Ferreira, Eliana B. Souto, Amélia M. Silva, and Lucinda V. Reis. "Quinoline- and Benzoselenazole-Derived Unsymmetrical Squaraine Cyanine Dyes: Design, Synthesis, Photophysicochemical Features and Light-Triggerable Antiproliferative Effects against Breast Cancer Cell Lines." Materials 13, no. 11 (June 10, 2020): 2646. http://dx.doi.org/10.3390/ma13112646.

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Photodynamic therapy is an innovative treatment approach broadly directed towards oncological diseases. Its applicability and efficiency are closely related to the interaction of three main components, namely a photosensitizer, light and molecular triplet oxygen, which should drive cell death. Recently, several studies have demonstrated that squaraine cyanine dyes have a set of photophysical and photochemical properties that have made of these compounds’ potential photosensitizers for this therapeutic modality. In the present research work, we describe the synthesis and characterization of four quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes. Except for the precursor of aminosquaraine dyes, i.e., O-methylated derivative, all dyes were evaluated for their behavior and absorption capacity in different organic and aqueous solvents, their ability to form singlet oxygen, their light-stability, and in vitro phototherapeutic effects against two human breast cancer cell cultures (BT-474 and MCF-7). Regardless of the nature of the used solvents, the synthesized dyes showed intense absorption in the red and near-infrared spectral regions, despite the formation of aggregates in aqueous media. Dyes showed high light-stability against light exposure. Despite the low ability to produce singlet oxygen, aminosquaraine dyes demonstrated worthy in vitro phototherapeutic activity.

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4

Lange, Natalia, Wojciech Szlasa, Jolanta Saczko, and Agnieszka Chwiłkowska. "Potential of Cyanine Derived Dyes in Photodynamic Therapy." Pharmaceutics 13, no. 6 (May 31, 2021): 818. http://dx.doi.org/10.3390/pharmaceutics13060818.

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Photodynamic therapy (PDT) is a method of cancer treatment that leads to the disintegration of cancer cells and has developed significantly in recent years. The clinically used photosensitizers are primarily porphyrin, which absorbs light in the red spectrum and their absorbance maxima are relatively short. This review presents group of compounds and their derivatives that are considered to be potential photosensitizers in PDT. Cyanine dyes are compounds that typically absorb light in the visible to near-infrared-I (NIR-I) spectrum range (750–900 nm). This meta-analysis comprises the current studies on cyanine dye derivatives, such as indocyanine green (so far used solely as a diagnostic agent), heptamethine and pentamethine dyes, squaraine dyes, merocyanines and phthalocyanines. The wide array of the cyanine derivatives arises from their structural modifications (e.g., halogenation, incorporation of metal atoms or organic structures, or synthesis of lactosomes, emulsions or conjugation). All the following modifications aim to increase solubility in aqueous media, enhance phototoxicity, and decrease photobleaching. In addition, the changes introduce new features like pH-sensitivity. The cyanine dyes involved in photodynamic reactions could be incorporated into sets of PDT agents.

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5

D. Martins, Tiago, Eurico Lima, Renato E. Boto, Diana Ferreira, José R. Fernandes, Paulo Almeida, Luis F. V. Ferreira, Amélia M. Silva, and Lucinda V. Reis. "Red and Near-Infrared Absorbing Dicyanomethylene Squaraine Cyanine Dyes: Photophysicochemical Properties and Anti-Tumor Photosensitizing Effects." Materials 13, no. 9 (May 1, 2020): 2083. http://dx.doi.org/10.3390/ma13092083.

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Photodynamic therapy is a medical modality developed for the treatment of several diseases of oncological and non-oncological etiology that requires the presence of a photosensitizer, light and molecular oxygen, which combined will trigger physicochemical reactions responsible for reactive oxygen species production. Given the scarcity of photosensitizers that exhibit desirable characteristics for its potential application in this therapeutic strategy, the main aims of this work were the study of the photophysical and photochemical properties and the photobiological activity of several dicyanomethylene squaraine cyanine dyes. Thus, herein, the study of their aggregation character, photobleaching and singlet oxygen production ability, and the further application of the previously synthesized dyes in Caco-2 and HepG2 cancer cell lines, to evaluate their phototherapeutic effects, are described. Dicyanomethylene squaraine dyes exhibited moderate light-stability and, despite the low singlet oxygen quantum yields, were a core of dyes that exhibited relevant in vitro photodynamic activity, as there was an evident increase in the toxicity of some of the tested dyes exclusive to radiation treatments.

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6

Qiao, Weiguo, and Zhong’an Li. "Recent Progress of Squaraine-Based Fluorescent Materials and Their Biomedical Applications." Symmetry 14, no. 5 (May 9, 2022): 966. http://dx.doi.org/10.3390/sym14050966.

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Squaraines (SQs) are unusual cyanine dyes with a unique resonance-stabilized zwitterionic structure. These dyes have attracted significant attention in the fields of organic electronics and organic photonics, due to their facile synthesis, intense and narrow visible and near-infrared absorption/emission, high photostability, low biotoxicity, etc. In this review, we summarize the recent progress of SQ-based fluorescent materials and their biomedical applications. After a brief introduction to SQs, general synthetic routes and design principles of SQ-based fluorescent materials, as well as their aggregation-induced luminescence behaviors, are discussed. Subsequently, their biomedical applications for cell imaging and as fluorescent sensors and therapeutic agents are introduced. Finally, a summary and perspective are given for promoting the development of SQs-based fluorescent materials.

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7

Terpetschnig, E. "Synthesis and characterization of unsymmetrical squaraines: a new class of cyanine dyes." Dyes and Pigments 21, no. 3 (1993): 227–34. http://dx.doi.org/10.1016/0143-7208(93)85016-s.

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8

TERPETSCHNIG, E., and J. R. LAKOWICZ. "ChemInform Abstract: Synthesis and Characterization of Unsymmetrical Squaraines: A New Class of Cyanine Dyes." ChemInform 25, no. 2 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199402240.

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9

Ma, Y. L., Shi Xue Ren, and Shi Yan Han. "Photo-Degradation Alkali Lignin by Bis-(2-Methyl Quinoline) Squarylium Cyanine TiO₂ Photocatalyst in Sunlight." Advanced Materials Research 838-841 (November 2013): 2717–20. http://dx.doi.org/10.4028/www.scientific.net/amr.838-841.2717.

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Photo-degradation alkali lignin was prepared in sunlight by the system of TiO2 and squaraine dye (QSC). The influence of the ratio of QSC to TiO2 on the solar energy conversion efficiency was tested; the principle of degradation alkali lignin by TiO2 photocatalyst in sunlight was researched. The results showed that the number-average and mass-average molecular mass of degradation alkali lignin and the control lignin were 1,548 and 2,822, respectively, the phenolic hydroxyl of degradation alkali lignin is 5.63% with the control is 4.64%, and alcoholic hydroxyl of degradation alkali lignin is 3.21% with the control is 3.77%.

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10

Grynyov, Roman S., Alexander V. Sorokin, Gleb Ya Guralchuk, Svetlana L. Yefimova, Igor A. Borovoy, and Yuri V. Malyukin. "Squaraine Dye as an Exciton Trap for Cyanine J-Aggregates in a Solution." Journal of Physical Chemistry C 112, no. 51 (November 24, 2008): 20458–62. http://dx.doi.org/10.1021/jp809124m.

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11

PONTREMOLI, Carlotta, Maria Jesus MORAN PLATA, Degnet Melese DEREJE, Ettore SANSONE, Giorgia CHINIGÒ, Alessandra FIORIO PLA, Sonja VISENTIN, Claudia BAROLO, and Nadia BARBERO. "The Effect of Substitutions on Squaraine and Cyanine dyes on their Photodynamic Activity." Photodiagnosis and Photodynamic Therapy 41 (March 2023): 103484. http://dx.doi.org/10.1016/j.pdpdt.2023.103484.

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12

PONTREMOLI, Carlotta, Maria Jesus MORAN PLATA, Degnet Melese DEREJE, Ettore SANSONE, Giorgia CHINIGÒ, Alessandra FIORIO PLA, Sonja VISENTIN, Claudia BAROLO, and Nadia BARBERO. "The Effect of Substitutions on Squaraine and Cyanine dyes on their Photodynamic Activity." Photodiagnosis and Photodynamic Therapy 41 (March 2023): 103385. http://dx.doi.org/10.1016/j.pdpdt.2023.103385.

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13

Saikiran, M., D. Sato, S. S. Pandey, and T. Kato. "Photophysical investigations of squaraine and cyanine dyes and their interaction with bovine serum albumin." Journal of Physics: Conference Series 704 (April 2016): 012012. http://dx.doi.org/10.1088/1742-6596/704/1/012012.

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14

Meador, William E., Shane A. Autry, Riley N. Bessetti, Jacqueline N. Gayton, Alex S. Flynt, Nathan I. Hammer, and Jared H. Delcamp. "Water-Soluble NIR Absorbing and Emitting Indolizine Cyanine and Indolizine Squaraine Dyes for Biological Imaging." Journal of Organic Chemistry 85, no. 6 (February 10, 2020): 4089–95. http://dx.doi.org/10.1021/acs.joc.9b03108.

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15

Markova, Larysa I., Ewald A. Terpetschnig, and Leonid D. Patsenker. "Comparison of a series of hydrophilic squaraine and cyanine dyes for use as biological labels." Dyes and Pigments 99, no. 3 (December 2013): 561–70. http://dx.doi.org/10.1016/j.dyepig.2013.06.022.

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16

Friães, Sofia, Eurico Lima, Renato E. Boto, Diana Ferreira, José R. Fernandes, Luis F. V. Ferreira, Amélia M. Silva, and Lucinda V. Reis. "Photophysicochemical Properties and In Vitro Phototherapeutic Effects of Iodoquinoline- and Benzothiazole-Derived Unsymmetrical Squaraine Cyanine Dyes." Applied Sciences 9, no. 24 (December 11, 2019): 5414. http://dx.doi.org/10.3390/app9245414.

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The search to replace conventional cancer treatment therapies, such as chemotherapy, radiotherapy and surgery has led over the last ten years, to a substantial effort in the development of several classes of photodynamic therapy photosensitizers with desired photophysicochemical and photobiological properties. Herein we report the synthesis of 6-iodoquinoline- and benzothiazole-based unsymmetrical squaraine cyanine dyes functionalized with amine groups located in the four-membered central ring. Their photodegradation and singlet oxygen production ability, as well as their in vitro photocytotoxicity against Caco-2 and HepG2 cell lines using a 630.8 ± 0.8 nm centered light-emitting diode system, were also investigated. All photosensitizer candidates displayed strong absorption within the tissue transparency spectral region (650–850 nm). The synthesized dyes were found to have moderate light stability. The potential of these compounds is evidenced by their cytotoxic activity against both tumor cell lines, highlighting the zwitterionic unsubstituted dye, which showed more intense photodynamic activity. Although the singlet oxygen quantum yields of these iodinated derivatives are considered low, it could be concluded that their introduction into the quinoline heterocycle was highly advantageous as it played a role in increasing selective cytotoxicity in the presence of light. Thus, the novel synthesized dyes present photophysicochemical and in vitro photobiological properties that make them excellent photosensitizer candidates for photodynamic therapy.

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17

Reddington, Mark V. "Synthesis and Properties of Phosphonic Acid Containing Cyanine and Squaraine Dyes for Use as Fluorescent Labels." Bioconjugate Chemistry 18, no. 6 (November 2007): 2178–90. http://dx.doi.org/10.1021/bc070090y.

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18

Lima, Eurico, Octávio Ferreira, Vanessa S. D. Gomes, Adriana O. Santos, Renato E. Boto, José R. Fernandes, Paulo Almeida, Samuel M. Silvestre, and Lucinda V. Reis. "Synthesis and in vitro evaluation of the antitumoral phototherapeutic potential of squaraine cyanine dyes derived from indolenine." Dyes and Pigments 167 (August 2019): 98–108. http://dx.doi.org/10.1016/j.dyepig.2019.04.007.

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19

Liu, Taihong, Xinglei Liu, Maira A. Valencia, Binglin Sui, Yuanwei Zhang, and Kevin D. Belfield. "Far-Red-Emitting TEG-Substituted Squaraine Dye: Synthesis, Optical Properties, and Selective Detection of Cyanide in Aqueous Solution." European Journal of Organic Chemistry 2017, no. 27 (July 20, 2017): 3957–64. http://dx.doi.org/10.1002/ejoc.201700649.

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20

Momicchioli, Fabio, Aleksandr S. Tatikolov, Davide Vanossi, and Glauco Ponterini. "Electronic structure and photochemistry of squaraine dyes: basic theoretical analysis and direct detection of the photoisomer of a symmetrical squarylium cyanine." Photochemical & Photobiological Sciences 3, no. 4 (2004): 396. http://dx.doi.org/10.1039/b315605b.

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21

Bigelow, Richard W., and Hans-Joachim Freund. "An MNDO and CNDO / S(S + DES CI) study on the structural and electronic properties of a model squaraine dye and related cyanine." Chemical Physics 107, no. 2-3 (September 1986): 159–74. http://dx.doi.org/10.1016/0301-0104(86)85001-7.

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22

Lei, Yuqing, Yuqian Wang, Sophie K. Hill, Zihe Cheng, Qiao Song, and Sébastien Perrier. "Supra‐Fluorophores: Ultrabright Fluorescent Supramolecular Assemblies Derived from Conventional Fluorophores in Water." Advanced Materials, February 28, 2024. http://dx.doi.org/10.1002/adma.202401346.

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AbstractFluorescent organic nanoparticles (NPs) with exceptional brightness hold significant promise for demanding fluorescence bioimaging applications. Although considerable efforts have been invested in developing novel organic dyes with enhanced performance, augmenting the brightness of conventional fluorophores is still one of the biggest challenges to overcome. In this study, we present a supramolecular strategy for constructing ultrabright fluorescent nanoparticles in aqueous media (referred to as “Supra‐fluorophores”) derived from conventional fluorophores. To achieve this, we have employed a cylindrical nanoparticle with a hydrophobic microdomain, assembled by a cyclic peptide‐diblock copolymer conjugate in water, as a supramolecular scaffold. The noncovalent dispersion of fluorophore moieties within the hydrophobic microdomain of the scaffold effectively mitigates the undesired aggregation‐caused quenching and fluorescence quenching by water, resulting in fluorescent NPs with high brightness. This strategy is applicable to a broad spectrum of fluorophore families, covering polyaromatic hydrocarbons, coumarins, boron‐dipyrromethenes, cyanines, xanthenes, and squaraines. The resulting fluorescent NPs demonstrate high fluorescence quantum yield (>30%) and brightness per volume (as high as 12 060 M−1 cm−1 nm−3). Moreover, high‐performance NPs with emission in the NIR region are constructed, showcasing up to 20‐fold increase in both brightness and photostability. Our Supra‐fluorophore strategy offers a versatile and effective method for transforming existing fluorophores into ultrabright fluorescent NPs in aqueous environments, for applications such as bioimaging.This article is protected by copyright. All rights reserved

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23

Meador, William E., Karina Kapusta, Iyanuoluwani Owolabi, Shane A. Autry, Julia Saloni, Wojciech Kolodziejczyk, Nathan I. Hammer, Alex S. Flynt, Glake A. Hill, and Jared Heath Delcamp. "Ultra Bright Near‐Infrared Sulfonate‐Indolizine Cyanine‐ and Squaraine‐Albumin Chaperones: Record Quantum Yields and Applications." ChemPhotoChem, June 20, 2022. http://dx.doi.org/10.1002/cptc.202200127.

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24

Meador, William E., Karina Kapusta, Iyanuoluwani Owolabi, Shane A. Autry, Julia Saloni, Wojciech Kolodziejczyk, Nathan I. Hammer, Alex S. Flynt, Glake A. Hill, and Jared H. Delcamp. "Ultra‐Bright Near‐Infrared Sulfonate‐Indolizine Cyanine‐ and Squaraine‐Albumin Chaperones: Record Quantum Yields and Applications." ChemPhotoChem 6, no. 9 (September 2022). http://dx.doi.org/10.1002/cptc.202200237.

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25

Meador, William E., Karina Kapusta, Iyanuoluwani Owolabi, Shane A. Autry, Julia Saloni, Wojciech Kolodziejczyk, Nathan I. Hammer, Alex S. Flynt, Glake A. Hill, and Jared H. Delcamp. "Front Cover: Ultra‐Bright Near‐Infrared Sulfonate‐Indolizine Cyanine‐ and Squaraine‐Albumin Chaperones: Record Quantum Yields and Applications (ChemPhotoChem 9/2022)." ChemPhotoChem 6, no. 9 (September 2022). http://dx.doi.org/10.1002/cptc.202200238.

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