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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 (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 (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 chai

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5

Wang, Mengzhe, Christopher D. McNitt, Hui Wang, et al. "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 (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 (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 (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 <sup>18</sup>F-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 (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, et al. "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 (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, et al. "Bioorthogonal Labeling, Bioimaging, and Photocytotoxicity Studies of Phosphorescent Ruthenium(II) Polypyridine Dibenzocyclooctyne Complexes." Chemistry - A European Journal 21, no. 30 (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 (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 (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 w

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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 (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 (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-isopropylacryl

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24

Kutovyi, Yurii, Jie Li, Ihor Zadorozhnyi, et al. "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-func

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25

Dharmatti, Miyatake, Nandakumar, et al. "Enhancement of Binding Affinity of Folate to Its Receptor by Peptide Conjugation." International Journal of Molecular Sciences 20, no. 9 (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 inter

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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 (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-encap

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27

Dadfar, Seyed Mohammad Mahdi, Sylwia Sekula-Neuner, Vanessa Trouillet, et al. "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-),

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28

Yang, Bingquan, Yangxin Wang, Mariia Vorobii, et al. "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 (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 (2013): 1207–14. http://dx.doi.org/10.1055/s-0032-1316875.

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30

Karsten, Lennard, Nils Janson, Vadim Le Joncour, et al. "Bivalent EGFR-Targeting DARPin-MMAE Conjugates." International Journal of Molecular Sciences 23, no. 5 (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 pro

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31

Porcello, Alexandre, Paula Gonzalez-Fernandez, Annick Jeannerat, et al. "Thermo-Responsive Hyaluronan-Based Hydrogels Combined with Allogeneic Cytotherapeutics for the Treatment of Osteoarthritis." Pharmaceutics 15, no. 5 (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 produc

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32

Hellwinkel, Dieter, and Siegbert Bohnet. "Dibenzocycloocten-, Dibenzochalcocin- und Diarenochalconindione." Chemische Berichte 120, no. 7 (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 (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 (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 (2010): 1156–59. http://dx.doi.org/10.1016/j.bse.2010.10.011.

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36

Moore, J. A., та T. D. Mitchell. "REGIOSELECTIVE FORMATION OF β-KETOAMIDES IN THE DIBENZOCYCLOOCTANE FAMILY". Organic Preparations and Procedures International 20, № 2 (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 (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 (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 (2005): 2288–93. http://dx.doi.org/10.1002/hlca.200590163.

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41

Friscourt, Frédéric, Petr A. Ledin, Ngalle Eric Mbua, et al. "Polar Dibenzocyclooctynes for Selective Labeling of Extracellular Glycoconjugates of Living Cells." Journal of the American Chemical Society 134, no. 11 (2012): 5381–89. http://dx.doi.org/10.1021/ja3002666.

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42

Liu, Xiaojun, Jian Zhang, Lin Shen, et al. "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 (2024): 3031. http://dx.doi.org/10.1200/jco.2024.42.16_suppl.3031.

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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 p

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43

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 (2017): 146–51. http://dx.doi.org/10.1002/ange.201711028.

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44

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 (2004): 2943–47. http://dx.doi.org/10.1002/hlca.200490265.

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45

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

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46

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 (2017): 140–45. http://dx.doi.org/10.1002/anie.201711028.

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47

Yang, Bing-You, Jiang-Tao Guo, Zu-Yi Li, et al. "New Thymoquinol Glycosides and Neuroprotective Dibenzocyclooctane Lignans from the Rattan Stems ofSchisandra chinensis." Chemistry & Biodiversity 13, no. 9 (2016): 1118–25. http://dx.doi.org/10.1002/cbdv.201500311.

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48

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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49

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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50

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 (2019): 8542–51. http://dx.doi.org/10.1021/acs.joc.9b00895.

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