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Journal articles on the topic 'Dibenzocyclooctyne'

Author: Grafiati

Published: 21 December 2024

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1

He, Yinming, Li Liu, and Liang Cheng. "A Short Review of Research Progress on the Synthesis Approaches of Aza-Dibenzocyclooctyne Derivatives." Molecules 28, no. 9 (April 25, 2023): 3715. http://dx.doi.org/10.3390/molecules28093715.

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Cyclooctyne molecules have found wide applications in the strain-promoted azide–alkyne cycloaddition (SPAAC) reactions, which avoid the biotoxicity caused by the use of Cu(I) catalysts. Among the various cyclooctyne systems, dibenzocyclooctyne (DBCO) series have displayed the highest reaction activity. However, the synthesis processes of such structures are time-consuming, which to some extent limit their large-scale development and application. This review has summarized current synthesis routes of two DBCO molecules, aza-dibenzocyclooctyne (DIBAC) and biarylazacyclooctynone (BARAC).

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2

Narayanam, Maruthi Kumar, Yong Liang, K. N. Houk, and Jennifer M. Murphy. "Discovery of new mutually orthogonal bioorthogonal cycloaddition pairs through computational screening." Chemical Science 7, no. 2 (2016): 1257–61. http://dx.doi.org/10.1039/c5sc03259h.

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3

Shenje, Learnmore, Yingqi Qu, Vladimir Popik, and Susanne Ullrich. "Femtosecond photodecarbonylation of photo-ODIBO studied by stimulated Raman spectroscopy and density functional theory." Physical Chemistry Chemical Physics 23, no. 45 (2021): 25637–48. http://dx.doi.org/10.1039/d1cp03512f.

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4

Adronov, Alex, Kelvin Li, and Stuart McNelles. "Preparation and Properties of a Hydrolytically Stable Cyclooctyne-Containing Polymer." Synlett 29, no. 19 (September 3, 2018): 2535–41. http://dx.doi.org/10.1055/s-0037-1610636.

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A poly[(phenylene vinylene)-co-dibenzocyclooctyne] polymer prepared by Wittig polymerization chemistry between dibenzocyclooctyne bisaldehyde [DIBO-(CHO)2] and bis(triethyleneglycol)phenylbis(tributylphosphonium) dibromide is reported. The resulting polymer exhibits moderate molecular weight (Mn: 10.5 kDa, Mw: 21.3 kDa, Ð: 2.02) and is fluorescent. It could be readily functionalized by strain-promoted alkyne-azide cycloadditon with different azides, and fluorescence of the polymer was preserved after functionalization. Grafting azide-terminated 5 kDa poly(ethylene glycol) monomethyl ether chains drastically affected the solubility of the polymer. Cross-linking the polymer with poly(ethylene glycol) that was terminated at both ends with azide groups gave access to a fluorescent organogel that could be dried and reswollen with water to form a hydrogel.

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5

Wang, Mengzhe, Christopher D. McNitt, Hui Wang, Xiaofen Ma, Sarah M. Scarry, Zhanhong Wu, Vladimir V. Popik, and Zibo Li. "The efficiency of 18F labelling of a prostate specific membrane antigen ligand via strain-promoted azide–alkyne reaction: reaction speed versus hydrophilicity." Chemical Communications 54, no. 56 (2018): 7810–13. http://dx.doi.org/10.1039/c8cc03999b.

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6

Kardelis, Vladimir, Ryan C. Chadwick, and Alex Adronov. "Click Functionalization of a Dibenzocyclooctyne-Containing Conjugated Polyimine." Angewandte Chemie International Edition 55, no. 3 (December 8, 2015): 945–49. http://dx.doi.org/10.1002/anie.201508639.

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7

Kardelis, Vladimir, Ryan C. Chadwick, and Alex Adronov. "Click Functionalization of a Dibenzocyclooctyne-Containing Conjugated Polyimine." Angewandte Chemie 128, no. 3 (December 8, 2015): 957–61. http://dx.doi.org/10.1002/ange.201508639.

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8

Moran, Joseph, Craig S. McKay, and John Paul Pezacki. "Strain-promoted 1,3-dipolar cycloadditions of diazo compounds with cyclooctynes." Canadian Journal of Chemistry 89, no. 2 (February 2011): 148–51. http://dx.doi.org/10.1139/v10-112.

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Strain-promoted cycloadditions of diazo compounds with dibenzocyclooctyne proceed with second-order rate constants of >10 L mol–1 s–1 at 25 °C. These reactions display rate constants that are comparable or greater than those of the analogous reactions of nitrones or azides with cyclooctynes.

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9

Kettenbach, K., and T. L. Ross. "A 18F-labeled dibenzocyclooctyne (DBCO) derivative for copper-free click labeling of biomolecules." MedChemComm 7, no. 4 (2016): 654–57. http://dx.doi.org/10.1039/c5md00508f.

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The new prosthetic group ¹⁸F-TEG-DBCO (dibenzocyclooctyne) can be prepared within a total reaction time of 60 min including purification with an overall yield (n.d.c.) of 34 ± 5%. Copper-free click cycloadditions with various biomolecule-azides resulted in very high RCYs under mild conditions.

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10

Djurdjevic, Sinisa, and James R. Green. "Nicholas Reactions in the Synthesis of Dicobalt Dibenzocyclooctyne Complexes." Organic Letters 15, no. 21 (October 14, 2013): 5468–71. http://dx.doi.org/10.1021/ol402617a.

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11

Ando, Takehiro, Yukio Takamori, Takumi Yokoyama, Mizuki Yamamoto, and Takashi Kawakami. "Directed evolution of dibenzocyclooctyne-reactive peptide tags for protein labeling." Biochemical and Biophysical Research Communications 534 (January 2021): 27–33. http://dx.doi.org/10.1016/j.bbrc.2020.12.002.

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12

Zeng, Zhiying, Changying Li, Yupeng Zhu, Lan Yang, Shuangquan Shi, Fengyuan Yang, and Xuli Feng. "Dibenzocyclooctyne linked lysine-cyclodextrin for efficient intranucleus delivery of proteins." Journal of Controlled Release 352 (December 2022): 759–65. http://dx.doi.org/10.1016/j.jconrel.2022.11.001.

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13

Yang, Xiaoke, Shuangshuang Wang, Yechao Yan, Ying Wu, Ke Zhang, and Yongming Chen. "Well-defined dibenzocyclooctyne end functionalized polymers from atom transfer radical polymerization." Polymer 55, no. 5 (March 2014): 1128–35. http://dx.doi.org/10.1016/j.polymer.2014.01.022.

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14

McNitt, Christopher D., and Vladimir V. Popik. "Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations." Organic & Biomolecular Chemistry 10, no. 41 (2012): 8200. http://dx.doi.org/10.1039/c2ob26581h.

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15

Lo, Kenneth Kam-Wing, Bruce Ting-Ngok Chan, Hua-Wei Liu, Kenneth Yin Zhang, Steve Po-Yam Li, and Tommy Siu-Ming Tang. "Cyclometalated iridium(iii) polypyridine dibenzocyclooctyne complexes as the first phosphorescent bioorthogonal probes." Chem. Commun. 49, no. 39 (2013): 4271–73. http://dx.doi.org/10.1039/c2cc36907a.

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16

Sun, Peng, Guowei Yan, Qingquan Tang, Yongming Chen, and Ke Zhang. "Well-defined cyclopropenone-masked dibenzocyclooctyne functionalized polymers from atom transfer radical polymerization." Polymer 64 (May 2015): 202–9. http://dx.doi.org/10.1016/j.polymer.2014.10.041.

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17

Qu, Lin, Ying Wu, Peng Sun, Ke Zhang, and Zhengping Liu. "Cyclopropenone-masked dibenzocyclooctyne end-functionalized polymers from reversible addition-fragmentation chain transfer polymerization." Polymer 114 (April 2017): 36–43. http://dx.doi.org/10.1016/j.polymer.2017.02.071.

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18

Tang, Tommy Siu-Ming, Alex Man-Hei Yip, Kenneth Yin Zhang, Hua-Wei Liu, Po Lam Wu, King Fai Li, Kok Wai Cheah, and Kenneth Kam-Wing Lo. "Bioorthogonal Labeling, Bioimaging, and Photocytotoxicity Studies of Phosphorescent Ruthenium(II) Polypyridine Dibenzocyclooctyne Complexes." Chemistry - A European Journal 21, no. 30 (June 19, 2015): 10729–40. http://dx.doi.org/10.1002/chem.201501040.

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19

Ding, Jin, Hang Su, Fan Wang, and Taiwei Chu. "A pre-targeting strategy for imaging glucose metabolism using technetium-99m labelled dibenzocyclooctyne derivative." Bioorganic & Medicinal Chemistry Letters 29, no. 14 (July 2019): 1791–98. http://dx.doi.org/10.1016/j.bmcl.2019.05.012.

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20

Choi, Alex Wing-Tat, Hua-Wei Liu, and Kenneth Kam-Wing Lo. "Rhenium(I) polypyridine dibenzocyclooctyne complexes as phosphorescent bioorthogonal probes: Synthesis, characterization, emissive behavior, and biolabeling properties." Journal of Inorganic Biochemistry 148 (July 2015): 2–10. http://dx.doi.org/10.1016/j.jinorgbio.2015.02.018.

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21

Osuofa, Joshua, and Scott M. Husson. "Preparation of Protein A Membrane Adsorbers Using Strain-Promoted, Copper-Free Dibenzocyclooctyne (DBCO)-Azide Click Chemistry." Membranes 13, no. 10 (October 6, 2023): 824. http://dx.doi.org/10.3390/membranes13100824.

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Protein A chromatography is the preferred unit operation for purifying Fc-based proteins. Convective chromatography technologies, like membrane adsorbers, can perform the purification rapidly and improve throughput dramatically. While the literature reports the preparation of Protein A membrane adsorbers utilizing traditional coupling chemistries that target lysine or thiol groups on the Protein A ligand, this study demonstrates a new approach utilizing copper-free dibenzocyclooctyne (DBCO)-azide click chemistry. The synthetic pathway consists of three main steps: bioconjugation of Protein A with a DBCO-polyethylene glycol (PEG) linker, preparation of an azide-functionalized membrane surface, and click reaction of DBCO-Protein A onto the membrane surface. Using polyclonal human immunoglobulins (hIgG) as the target molecule, Protein A membranes prepared by this synthetic pathway showed a flowrate-independent dynamic binding capacity of ~10 mg/mL membrane at 10% breakthrough. Fitting of static binding capacity measurements to the Langmuir adsorption isotherm showed a maximum binding (qmax) of 27.48 ± 1.31 mg/mL and an apparent equilibrium dissociation constant (Kd) of value of 1.72 × 10−1 ± 4.03 × 10−2 mg/mL. This work represents a new application for copper-less click chemistry in the membrane chromatography space and outlines a synthetic pathway that can be followed for immobilization of other ligands.

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22

Erickson, Patrick W., James M. Fulcher, Paul Spaltenstein, and Michael S. Kay. "Traceless Click-Assisted Native Chemical Ligation Enabled by Protecting Dibenzocyclooctyne from Acid-Mediated Rearrangement with Copper(I)." Bioconjugate Chemistry 32, no. 10 (October 8, 2021): 2233–44. http://dx.doi.org/10.1021/acs.bioconjchem.1c00403.

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23

Porcello, Alexandre, Paula Gonzalez-Fernandez, Olivier Jordan, and Eric Allémann. "Nanoforming Hyaluronan-Based Thermoresponsive Hydrogels: Optimized and Tunable Functionality in Osteoarthritis Management." Pharmaceutics 14, no. 3 (March 17, 2022): 659. http://dx.doi.org/10.3390/pharmaceutics14030659.

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Hyaluronic acid (HA) constitutes a versatile chemical framework for the development of osteoarthritis pain treatment by means of injection in the joints, so-called viscosupplementation. Without appropriate physico-chemical tuning, such preparations are inherently hindered by prompt in vivo degradation, mediated by hyaluronidases and oxidative stress. To prolong hydrogel residence time and confer optimized product functionality, novel thermoresponsive nanoforming HA derivatives were proposed and characterized. Combined use of sulfo-dibenzocyclooctyne-PEG4-amine linkers and poly(N-isopropylacrylamide) in green chemistry process enabled the synthesis of HA-based polymers, with in situ obtention of appropriate viscoelastic properties. Spontaneous and reversible thermoformation of nanoparticles above 30 °C was experimentally confirmed. Lead formulations were compared to a commercially available HA-based product and shown significantly better in vitro resistance to enzymatic and oxidative degradation, required half the injection force with optimal viscoelastic hydrogel properties in equine synovial fluids. Results highlighted the vast potential of appropriately engineered HA-based systems as next-generation long-acting viscosupplementation products for osteoarthritic patients.

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24

Kutovyi, Yurii, Jie Li, Ihor Zadorozhnyi, Hanna Hlukhova, Nazarii Boichuk, Dmytro Yehorov, Marcus Menger, and Svetlana Vitusevich. "Highly Sensitive and Fast Detection of C-Reactive Protein and Troponin Biomarkers Using Liquid-gated Single Silicon Nanowire Biosensors." MRS Advances 5, no. 16 (2020): 835–46. http://dx.doi.org/10.1557/adv.2020.60.

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ABSTRACTC-reactive protein (CRP) and cardiac troponin I (cTnI) biomolecules represent the earliest enzymes that appear in the blood when a cardiac injury occurs. Real-time and selective detection of these biomarkers is essential for the prediction and detection of cardiovascular diseases at an early stage. Here we report on the label-free specific detection of both proteins at picomolar concentrations using fabricated nanowire-based biosensors. We demonstrate a novel functionalization technique based on the attachment of dibenzocyclooctyne (DBCO)-linked troponin-specific aptamers to azide-functionalized silicon (Si) nanowire (NW) surface. Due to the fast and reliable immobilization of cTnI-specific aptamers and CRP-specific antibodies on the Si NWs, the fabricated devices can rapidly detect target biomolecules demonstrating high sensitivity. We confirm the attachment of proteins to the surface of Si NWs by atomic force microscopy (AFM). Moreover, we demonstrate that nanowire structures of different sizes enable the detection of biomarkers in a wide concentration range (from 1 pg/ml to 1 µg/ml), corresponding to CRP and cTnI elevation levels during the early stage of disease formation.

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25

Dharmatti, Miyatake, Nandakumar, Ueda, Kobayashi, Kiga, Yamamura, and Ito. "Enhancement of Binding Affinity of Folate to Its Receptor by Peptide Conjugation." International Journal of Molecular Sciences 20, no. 9 (April 30, 2019): 2152. http://dx.doi.org/10.3390/ijms20092152.

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(1) Background: The folate receptor (FR) is a target for cancer treatment and detection. Expression of the FR is restricted in normal cells but overexpressed in many types of tumors. Folate was conjugated with peptides for enhancing binding affinity to the FR. (2) Materials and Methods: For conjugation, folate was coupled with propargyl or dibenzocyclooctyne, and 4-azidophenylalanine was introduced in peptides for “click” reactions. We measured binding kinetics including the rate constants of association (ka) and dissociation (kd) of folate-peptide conjugates with purified FR by biolayer interferometry. After optimization of the conditions for the click reaction, we successfully conjugated folate with designed peptides. (3) Results: The binding affinity, indicated by the equilibrium dissociation constant (KD), of folate toward the FR was enhanced by peptide conjugation. The enhanced FR binding affinity by peptide conjugation is a result of an increase in the number of interaction sites. (4) Conclusion: Such peptide-ligand conjugates will be important in the design of ligands with higher affinity. These high affinity ligands can be useful for targeted drug delivery system.

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26

Au, Kin Man, Andrew Z. Wang, and Steven I. Park. "Pretargeted delivery of PI3K/mTOR small-molecule inhibitor–loaded nanoparticles for treatment of non-Hodgkin’s lymphoma." Science Advances 6, no. 14 (April 2020): eaaz9798. http://dx.doi.org/10.1126/sciadv.aaz9798.

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Overactivation of the PI3K/mTOR signaling has been identified in non-Hodgkin’s lymphoma. BEZ235 is an effective dual PI3K/mTOR inhibitor, but it was withdrawn from early-phase clinical trials owing to poor solubility and on-target/off-tumor toxicity. Here, we developed a nanoparticle (NP)–based pretargeted system for the therapeutic delivery of BEZ235 to CD20- and HLA-DR–expressing lymphoma cells for targeted therapy. The pretargeted system is composed of dibenzocyclooctyne-functionalized anti-CD20 and anti-Lym1 antibodies as the tumor-targeting components and azide-functionalized BEZ235-encapsulated NPs as the effector drug carrier. Using lymphoma cell lines with different CD20 and HLA-DR antigen densities as examples, we demonstrate that the dual antibody pretargeted strategy effectively raises the number of NPs retained on the target tumor cells and improves the in vitro and in vivo antitumor activity of BEZ235 through the inhibition of the PI3K/mTOR pathway. Our data demonstrate that the NP-based pretargeted system improves the therapeutic window of small-molecule kinase inhibitor.

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27

Dadfar, Seyed Mohammad Mahdi, Sylwia Sekula-Neuner, Vanessa Trouillet, Hui-Yu Liu, Ravi Kumar, Annie K. Powell, and Michael Hirtz. "Evaluation of click chemistry microarrays for immunosensing of alpha-fetoprotein (AFP)." Beilstein Journal of Nanotechnology 10 (December 16, 2019): 2505–15. http://dx.doi.org/10.3762/bjnano.10.241.

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The level of cancer biomarkers in cells, tissues or body fluids can be used for the prediction of the presence of cancer or can even indicate the stage of the disease. Alpha-fetoprotein (AFP) is the most commonly used biomarker for early screening and diagnosis of hepatocellular carcinoma (HCC). Here, a combination of three techniques (click chemistry, the biotin–streptavidin–biotin sandwich strategy and the use of antigen–antibody interactions) were combined to implement a sensitive fluorescent immunosensor for AFP detection. Three types of functionalized glasses (dibenzocyclooctyne- (DBCO-), thiol- and epoxy-terminated surfaces) were biotinylated by employing the respective adequate click chemistry counterparts (biotin–thiol or biotin–azide for the first class, biotin–maleimide or biotin–DBCO for the second class and biotin–amine or biotin–thiol for the third class). The anti-AFP antibody was immobilized on the surfaces via a biotin–streptavidin–biotin sandwich technique. To evaluate the sensing performance of the differently prepared surfaces, fluorescently labeled AFP was spotted onto them via microchannel cantilever spotting (µCS). Based on the fluorescence measurements, the optimal microarray design was found and its sensitivity was determined.

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28

Yang, Bingquan, Yangxin Wang, Mariia Vorobii, Eric Sauter, Meike Koenig, Ravi Kumar, Cesar Rodriguez‐Emmenegger, and Michael Hirtz. "Evaluation of Dibenzocyclooctyne and Bicyclononyne Click Reaction on Azido‐Functionalized Antifouling Polymer Brushes via Microspotting (Adv. Mater. Interfaces 16/2022)." Advanced Materials Interfaces 9, no. 16 (June 2022): 2270092. http://dx.doi.org/10.1002/admi.202270092.

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29

Golkowski, Martin, and Thomas Ziegler. "Synthesis of Tetra(2-hydroxyethoxy)-Substituted Dibenzocyclooctyne Derivatives as Novel, Highly Hydrophilic Tool Compounds for Strain-Promoted Alkyne-Azide Cycloaddition Applications." Synthesis 45, no. 09 (March 28, 2013): 1207–14. http://dx.doi.org/10.1055/s-0032-1316875.

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30

Karsten, Lennard, Nils Janson, Vadim Le Joncour, Sarfaraz Alam, Benjamin Müller, Jayendrakishore Tanjore Ramanathan, Pirjo Laakkonen, Norbert Sewald, and Kristian M. Müller. "Bivalent EGFR-Targeting DARPin-MMAE Conjugates." International Journal of Molecular Sciences 23, no. 5 (February 23, 2022): 2468. http://dx.doi.org/10.3390/ijms23052468.

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Epidermal growth factor receptor (EGFR) is a validated tumor marker overexpressed in various cancers such as squamous cell carcinoma (SSC) of the head and neck and gliomas. We constructed protein-drug conjugates based on the anti-EGFR Designed Ankyrin Repeat Protein (DARPin) E01, and compared the bivalent DARPin dimer (DD1) and a DARPin-Fc (DFc) to the monomeric DARPin (DM) and the antibody derived scFv425-Fc (scFvFc) in cell culture and a mouse model. The modular conjugation system, which was successfully applied for the preparation of protein-drug and -dye conjugates, uses bio-orthogonal protein-aldehyde generation by the formylglycine-generating enzyme (FGE). The generated carbonyl moiety is addressed by a bifunctional linker with a pyrazolone for a tandem Knoevenagel reaction and an azide for strain-promoted azide-alkyne cycloaddition (SPAAC). The latter reaction with a PEGylated linker containing a dibenzocyclooctyne (DBCO) for SPAAC and monomethyl auristatin E (MMAE) as the toxin provided the stable conjugates DD1-MMAE (drug-antibody ratio, DAR = 2.0) and DFc-MMAE (DAR = 4.0) with sub-nanomolar cytotoxicity against the human squamous carcinoma derived A431 cells. In vivo imaging of Alexa Fluor 647-dye conjugates in A431-xenografted mice bearing subcutaneous tumors as the SCC model revealed unspecific binding of bivalent DARPins to the ubiquitously expressed EGFR. Tumor-targeting was verified 6 h post-injection solely for DD1 and scFvFc. The total of four administrations of 6.5 mg/kg DD1-MMAE or DFc-MMAE twice weekly did not cause any sequela in mice. MMAE conjugates showed no significant anti-tumor efficacy in vivo, but a trend towards increased necrotic areas (p = 0.2213) was observed for the DD1-MMAE (n = 5).

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31

Porcello, Alexandre, Paula Gonzalez-Fernandez, Annick Jeannerat, Cédric Peneveyre, Philippe Abdel-Sayed, Corinne Scaletta, Wassim Raffoul, et al. "Thermo-Responsive Hyaluronan-Based Hydrogels Combined with Allogeneic Cytotherapeutics for the Treatment of Osteoarthritis." Pharmaceutics 15, no. 5 (May 18, 2023): 1528. http://dx.doi.org/10.3390/pharmaceutics15051528.

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Thermo-responsive hyaluronan-based hydrogels and FE002 human primary chondroprogenitor cell sources have both been previously proposed as modern therapeutic options for the management of osteoarthritis (OA). For the translational development of a potential orthopedic combination product based on both technologies, respective technical aspects required further optimization phases (e.g., hydrogel synthesis upscaling and sterilization, FE002 cytotherapeutic material stabilization). The first aim of the present study was to perform multi-step in vitro characterization of several combination product formulas throughout the established and the optimized manufacturing workflows, with a strong focus set on critical functional parameters. The second aim of the present study was to assess the applicability and the efficacy of the considered combination product prototypes in a rodent model of knee OA. Specific characterization results (i.e., spectral analysis, rheology, tribology, injectability, degradation assays, in vitro biocompatibility) of hyaluronan-based hydrogels modified with sulfo-dibenzocyclooctyne-PEG4-amine linkers and poly(N-isopropylacrylamide) (HA-L-PNIPAM) containing lyophilized FE002 human chondroprogenitors confirmed the suitability of the considered combination product components. Specifically, significantly enhanced resistance toward oxidative and enzymatic degradation was shown in vitro for the studied injectable combination product prototypes. Furthermore, extensive multi-parametric (i.e., tomography, histology, scoring) in vivo investigation of the effects of FE002 cell-laden HA-L-PNIPAM hydrogels in a rodent model revealed no general or local iatrogenic adverse effects, whereas it did reveal some beneficial trends against the development of knee OA. Overall, the present study addressed key aspects of the preclinical development process for novel biologically-based orthopedic combination products and shall serve as a robust methodological basis for further translational investigation and clinical work.

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32

Hellwinkel, Dieter, and Siegbert Bohnet. "Dibenzocycloocten-, Dibenzochalcocin- und Diarenochalconindione." Chemische Berichte 120, no. 7 (July 1987): 1151–73. http://dx.doi.org/10.1002/cber.19871200711.

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33

Chen, Min, Zhixin Liao, and Daofeng Chen. "Four New Dibenzocyclooctene Lignans fromKadsura renchangiana." Helvetica Chimica Acta 87, no. 6 (June 2004): 1368–76. http://dx.doi.org/10.1002/hlca.200490124.

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34

Ma, Wen-Hui, Yan Lu, and Dao-Feng Chen. "Dibenzocyclooctane Lignans from the Stems of Schisandra wilsoniana." Planta Medica 79, no. 12 (July 9, 2013): 1051–55. http://dx.doi.org/10.1055/s-0032-1328747.

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35

Ma, Wen-Hui, Jian-Cheng He, Peng-Shan Duan, Ting Han, Cheng-Jian Zheng, and Lu-Ping Qin. "Dibenzocyclooctane lignans from the stems of Schisandra bicolor." Biochemical Systematics and Ecology 38, no. 6 (December 2010): 1156–59. http://dx.doi.org/10.1016/j.bse.2010.10.011.

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36

Moore, J. A., and T. D. Mitchell. "REGIOSELECTIVE FORMATION OF β-KETOAMIDES IN THE DIBENZOCYCLOOCTANE FAMILY." Organic Preparations and Procedures International 20, no. 2 (April 1988): 135–43. http://dx.doi.org/10.1080/00304948809355801.

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37

Lu, Hua, and Geng-Tao Liu. "Anti-Oxidant Activity of Dibenzocyclooctene Lignans Isolated from Schisandraceae." Planta Medica 58, no. 04 (August 1992): 311–13. http://dx.doi.org/10.1055/s-2006-961473.

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38

Carroll, AR, and WC Taylor. "Intramolecular Oxidative Coupling of Aromatic Compounds. VI. An Efficient Synthesis of Some Dibenzocyclooctene Lignans." Australian Journal of Chemistry 47, no. 5 (1994): 937. http://dx.doi.org/10.1071/ch9940937.

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The 1,4-diaryl-2,3-dimethylbutanes (4) and (5) were readily prepared by reductive coupling of an arylacetone precursor followed by hydrogenation. Intramolecular oxidative coupling (dichlorodicyanobenzoquinone/trifluoroacetic acid) gave dibenzocyclooctene derivatives in good yield. (�)-Deoxyschizandrin and the corresponding trans isomer, existing in two distinct conformations, were prepared.

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39

Chen, Min, Xiumei Xu, Zhihua Liao, Li Dong, Lei Li, and Chengzhi Huang. "Neglschisandrins A-B: Two New Dibenzocyclooctene Lignans from Schisandra neglecta." Molecules 13, no. 3 (March 3, 2008): 548–55. http://dx.doi.org/10.3390/molecules13030548.

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40

Jia, Zhengwei, Zhixin Liao, and Daofeng Chen. "Two New Dibenzocyclooctene Lignans from the Water Extract ofKadsura spp." Helvetica Chimica Acta 88, no. 8 (August 2005): 2288–93. http://dx.doi.org/10.1002/hlca.200590163.

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Friscourt, Frédéric, Petr A. Ledin, Ngalle Eric Mbua, Heather R. Flanagan-Steet, Margreet A. Wolfert, Richard Steet, and Geert-Jan Boons. "Polar Dibenzocyclooctynes for Selective Labeling of Extracellular Glycoconjugates of Living Cells." Journal of the American Chemical Society 134, no. 11 (March 9, 2012): 5381–89. http://dx.doi.org/10.1021/ja3002666.

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Liu, Xiaojun, Jian Zhang, Lin Shen, Jieqiong Liu, Jian Huang, Zhixiang Zhuang, Yongmei Yin, Xiang Wang, Xian Wang, and Jiong Wu. "Evaluation of the safety, pharmacokinetics, and efficacy of JSKN003 in patients with advanced solid tumors: A phase I/II clinical study." Journal of Clinical Oncology 42, no. 16_suppl (June 1, 2024): 3031. http://dx.doi.org/10.1200/jco.2024.42.16_suppl.3031.

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Abstract:

3031 Background: JSKN003 is a bispecific HER2-directed antibody-drug conjugate (ADC) conjugated to a topoisomerase I inhibitor via a dibenzocyclooctyne tetrapeptide linker on the glycan of a humanized bispecific antibody. Pre-clinical studies showed that JSKN003 had a good serum stability, that may lead to a broader therapeutic window. Methods: JSKN003-102 (NCT05744427) is a phase I (dose escalation and dose expansion) and phase II (cohort expansion) study in Chinese patients (pts) with advanced solid tumors. Pts (ECOG PS 0-1) with HER2-expressing (IHC ≥ 1+) or HER2-mutant cancers who failed prior systemic therapies were recruited and received JSKN003 monotherapy intravenously Q3W. The objectives were safety, MTD or RP2D, pharmacokinetics, and preliminary antitumor activity. Here the results from phase I were reported. Results: As of 5th Jan 2024, 46 pts (25 breast cancers, 11 gastric cancers, 8 colorectal cancers, 1 lung cancer, and 1 ovarian cancer) were enrolled and received JSKN003 across 6 dose levels, including 2.1 (n=1), 4.2 (n=10), 5.2 (n=14), 6.3 (n=15), 7.3 (n=3), and 8.4 mg/kg (n=3), Q3W, in phase I period. Among the 46 pts, 18 were IHC 3+, 21 were IHC 2+, and 7 were IHC 1+. Most pts (73.9%) received ≥ 3 prior lines of therapy, including 60.9% and 45.6% of pts received prior anti-HER2 and anti-HER2 ADC therapy, respectively. The median duration of treatment was 13.1 (range, 2.1 - 42.4) weeks, and 37 pts (80.4%) remained on treatment. Treatment-related adverse events (TRAEs) occurred in 44 pts (95.7%), and the common, mostly grade 1 and 2, were diarrhea (37.0%) and nausea (32.6%). Only 6 pts (13.0%) experienced grade ≥3 TRAEs, and the common were lymphopenia (4.3%) and neutropenia(4.3%). 1 pt (2.2%) had treatment related SAE (nausea, grade 3). No pts experienced DLT or interstitial lung disease, and no TRAE led to death or discontinuation. Following a single dose, exposures (Cmax and AUC) of JSKN003 increased proportionally over a dose range of 4.2 mg/kg to 6.3mg/kg. T1/2 of JSKN003 is approximately 3-5 days. No significant accumulation was observed after 4 cycles treatment. The exposure of released payload was very low, demonstrating the stability of the JSKN003 in circulation. 37 pts had at least one post-baseline tumor assessment. The ORR and DCR was 51.4% (95%CI: 34.4, 68.1) and 91.9% (95%CI: 78.1, 98.3), respectively. The ORR in pts with HER2 IHC 1+, 2+ and 3+ was 20.0% (95% CI: 0.5, 71.6), 33.3% (95% CI: 11.8, 61.6), and 76.5% (95% CI: 50.1, 93.2), respectively. For pts who received prior anti-HER2 ADC, the ORR was 57.9% (95% CI: 33.5, 79.7). For HER2 positive breast cancer and gastric cancer, the ORR was 66.7% (95% CI: 38.4, 88.2) in 15 pts and 100% (95% CI: 39.8, 100) in 4 pts, respectively. Conclusions: MTD of JSKN003 was not reached yet. And safety of JSKN003 was extremely excellent with encouraging preliminary antitumor activity in heavily pretreated pts with advanced solid tumors. Clinical trial information: NCT05744427 .

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te Grotenhuis, Colet, Naudin van den Heuvel, Jarl Ivar van der Vlugt, and Bas de Bruin. "Catalytic Dibenzocyclooctene Synthesis via Cobalt(III)-Carbene Radical and ortho -Quinodimethane Intermediates." Angewandte Chemie 130, no. 1 (December 6, 2017): 146–51. http://dx.doi.org/10.1002/ange.201711028.

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Li, Liang, Hai-Ying Ren, Xiao-Dong Yang, Jing-Feng Zhao, Gan-Peng Li, and Hong-Bin Zhang. "Rubriflorin A and B, Two Novel Partially Saturated Dibenzocyclooctene Lignans fromSchisandra rubriflora." Helvetica Chimica Acta 87, no. 11 (November 2004): 2943–47. http://dx.doi.org/10.1002/hlca.200490265.

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Lu, Yan, and Daofeng Chen. "Kadsutherins A–C: Three New Dibenzocyclooctane Lignans from the Stems ofKadsura Species." Helvetica Chimica Acta 89, no. 5 (May 2006): 895–901. http://dx.doi.org/10.1002/hlca.200690092.

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te Grotenhuis, Colet, Naudin van den Heuvel, Jarl Ivar van der Vlugt, and Bas de Bruin. "Catalytic Dibenzocyclooctene Synthesis via Cobalt(III)-Carbene Radical and ortho -Quinodimethane Intermediates." Angewandte Chemie International Edition 57, no. 1 (December 6, 2017): 140–45. http://dx.doi.org/10.1002/anie.201711028.

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Yang, Bing-You, Jiang-Tao Guo, Zu-Yi Li, Chang-Fu Wang, Zhi-Bin Wang, Qiu-Hong Wang, and Hai-Xue Kuang. "New Thymoquinol Glycosides and Neuroprotective Dibenzocyclooctane Lignans from the Rattan Stems ofSchisandra chinensis." Chemistry & Biodiversity 13, no. 9 (September 2016): 1118–25. http://dx.doi.org/10.1002/cbdv.201500311.

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Pelter, Andrew, Peter Satchwell, Robert S. Ward, and Keith Blake. "Effective, direct biomimetic synthesis of dibenzocyclooctene lignans by hypervalent iodine oxidation of phenolic dibenzylbutyrolactones." Journal of the Chemical Society, Perkin Transactions 1, no. 18 (1995): 2201. http://dx.doi.org/10.1039/p19950002201.

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XUE, J., G. LIU, H. WEI, and Y. PAN. "Antioxidant activity of two dibenzocyclooctene lignans on the aged and ischemic brain in rats☆." Free Radical Biology and Medicine 12, no. 2 (1992): 127–35. http://dx.doi.org/10.1016/0891-5849(92)90006-3.

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Terzic, Vida, Guillaume Pousse, Rachel Méallet-Renault, Philippe Grellier, and Joëlle Dubois. "Dibenzocyclooctynes: Effect of Aryl Substitution on Their Reactivity toward Strain-Promoted Alkyne–Azide Cycloaddition." Journal of Organic Chemistry 84, no. 13 (June 3, 2019): 8542–51. http://dx.doi.org/10.1021/acs.joc.9b00895.

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