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Journal articles on the topic 'Trans-cyclooctene'

Author: Grafiati

Published: 4 June 2025

Last updated: 1 August 2025

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1

Wang, Ke, Danzhu Wang, Kaili Ji, et al. "Post-synthesis DNA modifications using a trans-cyclooctene click handle." Organic & Biomolecular Chemistry 13, no. 3 (2015): 909–15. http://dx.doi.org/10.1039/c4ob02031f.

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Efficient enzymatic DNA incorporation of trans-cyclooctene thymidine triphosphate (TCO-TTP) is reported. The general handle of trans-cyclooctene can undergo a rapid bioorthogonal cycloaddition with tetrazine, which is suitable for further DNA labeling work.

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2

de Geus, Mark A. R., G. J. Mirjam Groenewold, Elmer Maurits, Can Araman, and Sander I. van Kasteren. "Synthetic methodology towards allylic trans-cyclooctene-ethers enables modification of carbohydrates: bioorthogonal manipulation of the lac repressor." Chemical Science 11, no. 37 (2020): 10175–79. http://dx.doi.org/10.1039/d0sc03216f.

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Two novel reagents were developed to direct formation of allylic cis-cyclooctene (CCO) ethers, followed by photochemical isomerization to obtain trans-cyclooctene (TCO) ethers. The method was used to cage a bio-active carbohydrate.

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3

Kiss, Loránd, Enikő Forró, and Ferenc Fülöp. "Novel stereocontrolled syntheses of tashiromine and epitashiromine." Beilstein Journal of Organic Chemistry 11 (April 30, 2015): 596–603. http://dx.doi.org/10.3762/bjoc.11.66.

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A novel stereocontrolled approach has been developed for the syntheses of tashiromine and epitashiromine alkaloids from cyclooctene β-amino acids. The synthetic concept is based on the azetidinone opening of a bicyclic β-lactam, followed by oxidative ring opening through ring C–C double bond and reductive ring-closure reactions of the cis- or trans-cyclooctene β-amino acids.

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4

Matikonda, Siddharth S., Douglas L. Orsi, Verena Staudacher, et al. "Bioorthogonal prodrug activation driven by a strain-promoted 1,3-dipolar cycloaddition." Chemical Science 6, no. 2 (2015): 1212–18. http://dx.doi.org/10.1039/c4sc02574a.

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5

Asare-Okai, P. N., E. Agustin, D. Fabris, and M. Royzen. "Site-specific fluorescence labelling of RNA using bio-orthogonal reaction of trans-cyclooctene and tetrazine." Chem. Commun. 50, no. 58 (2014): 7844–47. http://dx.doi.org/10.1039/c4cc02435d.

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6

Regeta, Khrystyna, Amit Nagarkar, Andreas F. M. Kilbinger, and Michael Allan. "Transient anions of cis- and trans-cyclooctene studied by electron-impact spectroscopy." Physical Chemistry Chemical Physics 17, no. 6 (2015): 4696–700. http://dx.doi.org/10.1039/c4cp04083j.

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7

Vázquez, Arcadio, Rastislav Dzijak, Martin Dračínský, Robert Rampmaier, Sebastian J. Siegl, and Milan Vrabel. "Mechanism-Based Fluorogenic trans -Cyclooctene-Tetrazine Cycloaddition." Angewandte Chemie International Edition 56, no. 5 (2016): 1334–37. http://dx.doi.org/10.1002/anie.201610491.

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8

Zhou, Yimin, Roy C. H. Wong, Gaole Dai, and Dennis K. P. Ng. "A bioorthogonally activatable photosensitiser for site-specific photodynamic therapy." Chemical Communications 56, no. 7 (2020): 1078–81. http://dx.doi.org/10.1039/c9cc07938f.

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Inverse-electron-demand Diels–Alder reaction of a 1,2,4,5-tetrazine-substituted boron dipyrromethene with a biotin-conjugated trans-cyclooctene results in site-specific activation of the photoactivity of the former photosensitiser.

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9

Johann, Kerstin, Dennis Svatunek, Christine Seidl, et al. "Tetrazine- and trans-cyclooctene-functionalised polypept(o)ides for fast bioorthogonal tetrazine ligation." Polymer Chemistry 11, no. 27 (2020): 4396–407. http://dx.doi.org/10.1039/d0py00375a.

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Tetrazine- and trans-cyclooctene-functionalised polypeptides and polypetoids were prepared by ring-opening polymerisation of N-carboxyanhydrides using the respective functional initiators and shown to react in fast bioorthogonal tetrazine ligations.

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10

Zhang, Yajie, Hong Chen, Tingting Zhang, et al. "Fast-forming BMSC-encapsulating hydrogels through bioorthogonal reaction for osteogenic differentiation." Biomaterials Science 6, no. 10 (2018): 2578–81. http://dx.doi.org/10.1039/c8bm00689j.

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An injectable in situ fast-forming hydrogel was fabricated to encapsulate BMSCs for osteogenic differentiation through the inverse electron demand Diels–Alder click reaction between trans-cyclooctene-modified PEG and tetrazine-modified hyaluronic acid.

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11

Yazdani, Abdolreza, Nancy Janzen, Shannon Czorny, et al. "Preparation of tetrazine-containing [2 + 1] complexes of 99mTc and in vivo targeting using bioorthogonal inverse electron demand Diels–Alder chemistry." Dalton Transactions 46, no. 42 (2017): 14691–99. http://dx.doi.org/10.1039/c7dt01497j.

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A new <sup>99m</sup>Tc-labelled tetrazine for targeted imaging using bioorthogonal chemistry was developed and evaluated in vivo using a trans-cyclooctene derived bisphosphonate targeting regions of high bone turnover and bone lesions.

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12

Teh, Jin Hui, Marta Braga, Louis Allott, et al. "A kit-based aluminium-[¹⁸F]fluoride approach to radiolabelled microbubbles." Chemical Communications 57, no. 88 (2021): 11677–80. http://dx.doi.org/10.1039/d1cc04790f.

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A facile, kit-based method for 18F-labelling of ultrasound microbubble contrast agents is reported using the IEDDA ligation between a trans-cyclooctene modified phospholipid and a [18F]AlF-tetrazine tracer, enabling in vivo tracking of microbubbles.

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13

Jean, Stéphanie, Kevin Cormier, Alyssa E. Patterson, et al. "Synthesis, characterization, and anticancer properties of organometallic Schiff base platinum complexes." Canadian Journal of Chemistry 93, no. 10 (2015): 1140–46. http://dx.doi.org/10.1139/cjc-2015-0157.

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A small family of organometallic platinum complexes containing a chloride, cis-cyclooctene, and a Schiff base ligand have been prepared and characterized fully. Three aliphatic amines and four aromatic amines were chosen as representative examples. All complexes were stable in air except for 7, derived from the pinacol-protected 4-aminophenylboronate ester 4-H2NC6H4Bpin (pin = 1,2-O2C2Me4), which decomposed via B–C bond cleavage. Both complexes 4 (derived from aniline) and 7 were further characterized by single-crystal X-ray diffraction studies and confirmed the square planar nature of the pla

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14

Hernández-Gil, Javier, Marta Braga, Bethany I. Harriss, et al. "Development of 68Ga-labelled ultrasound microbubbles for whole-body PET imaging." Chemical Science 10, no. 21 (2019): 5603–15. http://dx.doi.org/10.1039/c9sc00684b.

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We report a rapid and efficient method for labelling ultrasound microbubble (MB) agents with a generator-produced PET isotope using a facile ligation between a trans-cyclooctene-modified phospholipid and a new <sup>68</sup>Ga-HBED-CC-tetrazine tracer. This method provides accessible solutions for in vivo tracking of MBs.

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15

van Onzen, Arthur H. A. M., Ron M. Versteegen, Freek J. M. Hoeben, et al. "Bioorthogonal Tetrazine Carbamate Cleavage by Highly Reactive trans-Cyclooctene." Journal of the American Chemical Society 142, no. 25 (2020): 10955–63. http://dx.doi.org/10.1021/jacs.0c00531.

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16

Selvaraj, Ramajeyam, and Joseph M. Fox. "trans-Cyclooctene—a stable, voracious dienophile for bioorthogonal labeling." Current Opinion in Chemical Biology 17, no. 5 (2013): 753–60. http://dx.doi.org/10.1016/j.cbpa.2013.07.031.

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17

Leong, Max K., Vladimir S. Mastryukov, and James E. Boggs. "Structure and conformation of cyclopentene, cycloheptene and trans-cyclooctene." Journal of Molecular Structure 445, no. 1-3 (1998): 149–60. http://dx.doi.org/10.1016/s0022-2860(98)00421-9.

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18

Darko, Ampofo, Joseph Fox, and Samantha Boyd. "Large-Scale Flow Photochemical Synthesis of Functionalized trans-Cyclooctenes Using Sulfonated Silica Gel." Synthesis 50, no. 24 (2018): 4875–82. http://dx.doi.org/10.1055/s-0037-1610240.

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Functionalized trans-cyclooctenes are useful bioorthogonal reagents that are typically prepared using a flow photoisomerization method in which the product is captured by AgNO3 on silica gel. While this method is effective, the leaching of silver can be problematic when scaling up syntheses. It is shown here that Ag(I) immobilized on tosic silica gel can be used to capture trans-cyclooctene products at higher loadings without leaching. It is demonstrated that the sulfonated silica gel can be regenerated and reused with similar yields over multiple runs. Nine different trans-cyclooctenes were s

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19

Böttcher, Hans-Christian, та Peter Mayer. "The Crystal Structure of trans-[{Rh(μ-Cl)(CO)(coe)}2 ] (coe = cis-cyclooctene)". Zeitschrift für Naturforschung B 63, № 3 (2008): 342–44. http://dx.doi.org/10.1515/znb-2008-0320.

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Single crystals of trans-[{Rh(μ-Cl)(CO)(coe)}2] (1) obtained from the reaction of [{Rh(μ-Cl)(coe)2}2] (coe = cis-cyclooctene) with carbon monoxide have been analyzed by X-ray crystallography (monoclinic, C2/c, Z = 4, a = 15.6271(4), b = 13.6943(4), c = 10.4169(2) Å ; β = 115.3549(17)°; V = 2014.50(9) Å3; T = 200(2) K).

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20

van den Broek, Sara Lopes, Vladimir Shalgunov, Gitte Knudsen, Dag Sehlin, Stina Syvaenen та Matthias Herth. "Trans-cyclooctene modified antibodies for pretargeted imaging of amyloid-β". Nuclear Medicine and Biology 108-109 (травень 2022): S98—S99. http://dx.doi.org/10.1016/s0969-8051(22)00226-8.

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21

Lorenzo, Maltish M., Caitlin G. Decker, Muhammet U. Kahveci, Samantha J. Paluck, and Heather D. Maynard. "Homodimeric Protein–Polymer Conjugates via the Tetrazine–trans-Cyclooctene Ligation." Macromolecules 49, no. 1 (2015): 30–37. http://dx.doi.org/10.1021/acs.macromol.5b02323.

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22

Greenberg, Arthur, and Deyi Yang. "Comparison of reactions of difluorocarbene with cis- and trans-cyclooctene." Journal of Organic Chemistry 55, no. 1 (1990): 372–73. http://dx.doi.org/10.1021/jo00288a071.

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23

van de Graaff, Michel J., Timo Oosenbrug, Mikkel H. S. Marqvorsen, et al. "Conditionally Controlling Human TLR2 Activity via Trans-Cyclooctene Caged Ligands." Bioconjugate Chemistry 31, no. 6 (2020): 1685–92. http://dx.doi.org/10.1021/acs.bioconjchem.0c00237.

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24

Keinänen, Outi, Ermei M. Mäkilä, Rici Lindgren, et al. "Pretargeted PET Imaging of trans-Cyclooctene-Modified Porous Silicon Nanoparticles." ACS Omega 2, no. 1 (2017): 62–69. http://dx.doi.org/10.1021/acsomega.6b00269.

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25

Auchynnikava, Tatsiana, Antti Äärelä, Heidi Liljenbäck, et al. "Pretargeted PET imaging of trans-cyclooctene functionalized spherical nucleic acids." Nuclear Medicine and Biology 126-127 (November 2023): 108699. http://dx.doi.org/10.1016/j.nucmedbio.2023.108699.

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26

Timperanza, Chiara, Holger Jensen, Tom Bäck, Sture Lindegren, and Emma Aneheim. "Pretargeted Alpha Therapy of Disseminated Cancer Combining Click Chemistry and Astatine-211." Pharmaceuticals 16, no. 4 (2023): 595. http://dx.doi.org/10.3390/ph16040595.

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To enhance targeting efficacy in the radioimmunotherapy of disseminated cancer, several pretargeting strategies have been developed. In pretargeted radioimmunotherapy, the tumor is pretargeted with a modified monoclonal antibody that has an affinity for both tumor antigens and radiolabeled carriers. In this work, we aimed to synthesize and evaluate poly-L-lysine-based effector molecules for pretargeting applications based on the tetrazine and trans-cyclooctene reaction using 211At for targeted alpha therapy and 125I as a surrogate for the imaging radionuclides 123, 124I. Poly-L-lysine in two s

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27

Ren, Xiaomei, Afaf H. El-Sagheer, and Tom Brown. "Azide and trans-cyclooctene dUTPs: incorporation into DNA probes and fluorescent click-labelling." Analyst 140, no. 8 (2015): 2671–78. http://dx.doi.org/10.1039/c5an00158g.

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28

Darko, Ampofo, Stephen Wallace, Olga Dmitrenko, et al. "Conformationally strained trans-cyclooctene with improved stability and excellent reactivity in tetrazine ligation." Chem. Sci. 5, no. 10 (2014): 3770–76. http://dx.doi.org/10.1039/c4sc01348d.

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29

Vázquez, Rocío García, Umberto Battisti, Vladimir Shalgunov, Gabriela Schäfer, Matthias Barz, and Matthias Herth. "[11C]Carboxylated tetrazines for facile labeling of trans-cyclooctene-functionalized macromolecules." Nuclear Medicine and Biology 108-109 (May 2022): S71—S72. http://dx.doi.org/10.1016/s0969-8051(22)00175-5.

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30

Braddock, D. Christopher, Gemma Cansell, Stephen A. Hermitage, and Andrew J. P. White. "An asymmetric synthesis of enantiopure chair and twist trans-cyclooctene isomers." Tetrahedron: Asymmetry 15, no. 19 (2004): 3123–29. http://dx.doi.org/10.1016/j.tetasy.2004.07.036.

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31

Pedersen, Thomas Bondo, and Henrik Koch. "Theoretical electronic absorption and natural circular dichroism spectra of (−)-trans-cyclooctene." Journal of Chemical Physics 112, no. 5 (2000): 2139–47. http://dx.doi.org/10.1063/1.480826.

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32

Demonceau, Albert, François Simal, Corine A. Lemoine, Alfred F. Noels, Igor T. Chizhevsky, and Pavel V. Sorokin. "[OsH4(PPh3)3]: New Catalyst for the Selective Cyclopropanation of Activated Olefins." Collection of Czechoslovak Chemical Communications 61, no. 12 (1996): 1798–804. http://dx.doi.org/10.1135/cccc19961798.

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The title compound was found to be an efficient catalyst for the selective cyclopropanation of activated olefins by ethyl diazoacetate. The cyclopropane yields range from moderate to good (75 to 95%) for activated olefins such as styrene and styrene derivatives, but are rather low (20 to 30%) for non-activated olefins such as terminal and cyclic alkenes. In the intermolecular competition, styrene was 45 times more reactive than cyclooctene. In all cases, trans (exo) cyclopropane predominated over the cis (endo) isomer.

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33

He, Xiao-Feng, Christopher M. Vogels, Andreas Decken, and Stephen A. Westcott. "2-Thiophen-2-ylbenzothiazole, -benzoxazole, and -benzimidazole platinum complexes." Canadian Journal of Chemistry 81, no. 7 (2003): 861–65. http://dx.doi.org/10.1139/v03-094.

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Oxidative cyclization of 2-aminothiophenol, 2-aminophenol, and 1,2-phenylenediamine with 2-thiophenecarboxaldehyde affords the corresponding 2-thiophen-2-ylbenzothiazole, -benzoxazole, and -benzimidazole compounds. Addition of these ligands (L) to [PtCl2(coe)]2 (coe = cis-cyclooctene) gives complexes of the type trans-PtCl2L(coe) in moderate yields. Crystals of the benzothiazole derivative (1) were monoclinic, space group P2(1)/c, a = 11.561(4) Å, b = 15.335(15) Å, c = 11.769(4) Å, β = 105.182(5)°, Z = 4.Key words: platinum, imine, benzothiazole, benzoxazole, benzimidazole.

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34

Wang, Ping, Zhenkun Na, Jiaqi Fu, et al. "Microarray immobilization of biomolecules using a fast trans-cyclooctene (TCO)–tetrazine reaction." Chem. Commun. 50, no. 80 (2014): 11818–21. http://dx.doi.org/10.1039/c4cc03838j.

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35

Li, Zibo, Hancheng Cai, Matthew Hassink, et al. "Tetrazine–trans-cyclooctene ligation for the rapid construction of 18F labeled probes." Chemical Communications 46, no. 42 (2010): 8043. http://dx.doi.org/10.1039/c0cc03078c.

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36

Traylor, Teddy G., Yassuko Iamamoto, and Taku Nakano. "Mechanisms of hemin-catalyzed oxidations: rearrangements during the epoxidation of trans-cyclooctene." Journal of the American Chemical Society 108, no. 12 (1986): 3529–31. http://dx.doi.org/10.1021/ja00272a070.

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37

Herth, Matthias M., Valdemar L. Andersen, Szabolcs Lehel, Jacob Madsen, Gitte M. Knudsen, and Jesper L. Kristensen. "Development of a 11C-labeled tetrazine for rapid tetrazine–trans-cyclooctene ligation." Chemical Communications 49, no. 36 (2013): 3805. http://dx.doi.org/10.1039/c3cc41027g.

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38

Stauch, Tim, Jan Felix Scholtes, and Andreas Dreuw. "Rational design of improved dienophiles for in vivo tetrazine-trans-cyclooctene ligation." Chemical Physics Letters 654 (June 2016): 6–8. http://dx.doi.org/10.1016/j.cplett.2016.04.044.

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39

Siegl, Sebastian J., Juraj Galeta, Rastislav Dzijak, et al. "An Extended Approach for the Development of Fluorogenic trans ‐Cyclooctene–Tetrazine Cycloadditions." ChemBioChem 20, no. 7 (2019): 886–90. http://dx.doi.org/10.1002/cbic.201800711.

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40

Adam, Waldemar, Chantu R. Saha-Moeller, and Oliver Weichold. "ChemInform Abstract: Epoxidation of trans-Cyclooctene by Methyltrioxorhenium/H2O2: Reaction of trans-Epoxide with the Monoperoxo Complex." ChemInform 31, no. 49 (2000): no. http://dx.doi.org/10.1002/chin.200049095.

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41

Liang, Dongjun, Kane Wu, Reika Tei, Timothy W. Bumpus, Johnny Ye, and Jeremy M. Baskin. "A real-time, click chemistry imaging approach reveals stimulus-specific subcellular locations of phospholipase D activity." Proceedings of the National Academy of Sciences 116, no. 31 (2019): 15453–62. http://dx.doi.org/10.1073/pnas.1903949116.

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The fidelity of signal transduction requires spatiotemporal control of the production of signaling agents. Phosphatidic acid (PA) is a pleiotropic lipid second messenger whose modes of action differ based on upstream stimulus, biosynthetic source, and site of production. How cells regulate the local production of PA to effect diverse signaling outcomes remains elusive. Unlike other second messengers, sites of PA biosynthesis cannot be accurately visualized with subcellular precision. Here, we describe a rapid, chemoenzymatic approach for imaging physiological PA production by phospholipase D (

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42

Wood, John L., Patrick J. Carroll, and Amos B. Smith. "Novel structures of a trans-cyclooctene and trans-fused cyclopropane generated via photoisomerization of a gem-dichlorocyclopropyl-benzocycloheptenone." Journal of the Chemical Society, Chemical Communications, no. 19 (1992): 1433. http://dx.doi.org/10.1039/c39920001433.

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43

Echalier, Cécile, Anna Rutkowska, Ana Kojic, et al. "amTCO, a new trans-cyclooctene derivative to study drug-target interactions in cells." Chemical Communications 57, no. 14 (2021): 1814–17. http://dx.doi.org/10.1039/d0cc06709a.

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44

Adhikari, Karuna, Filipe Elvas, Sigrid Stroobants, Pieter Van der Veken, and Koen Augustyns. "Development and evaluaton of a trans-cyclooctene (TCO) probe for pretargeted PET imaging." Nuclear Medicine and Biology 108-109 (May 2022): S176. http://dx.doi.org/10.1016/s0969-8051(22)00370-5.

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45

Xu, Lujuan, Marco Raabe, Maksymilian M. Zegota, et al. "Site-selective protein modification via disulfide rebridging for fast tetrazine/trans-cyclooctene bioconjugation." Organic & Biomolecular Chemistry 18, no. 6 (2020): 1140–47. http://dx.doi.org/10.1039/c9ob02687h.

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46

Chiang, Y., and A. J. Kresge. "Mechanism of hydration of simple olefins in aqueous solution. cis- and trans-Cyclooctene." Journal of the American Chemical Society 107, no. 22 (1985): 6363–67. http://dx.doi.org/10.1021/ja00308a033.

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47

Inoue, Yoshihisa, Taizo Yokoyama, Noritsugu Yamasaki, and Akira Tai. "Temperature switching of product chirality upon photosensitized enantiodifferentiating cis-trans isomerization of cyclooctene." Journal of the American Chemical Society 111, no. 16 (1989): 6480–82. http://dx.doi.org/10.1021/ja00198a101.

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48

Chaudhuri, Samata, Till Korten, and Stefan Diez. "Tetrazine–trans-cyclooctene Mediated Conjugation of Antibodies to Microtubules Facilitates Subpicomolar Protein Detection." Bioconjugate Chemistry 28, no. 4 (2017): 918–22. http://dx.doi.org/10.1021/acs.bioconjchem.7b00118.

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49

Taylor, Michael T., Melissa L. Blackman, Olga Dmitrenko, and Joseph M. Fox. "Design and Synthesis of Highly Reactive Dienophiles for the Tetrazine–trans-Cyclooctene Ligation." Journal of the American Chemical Society 133, no. 25 (2011): 9646–49. http://dx.doi.org/10.1021/ja201844c.

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50

Yamasaki, Noritsugu, Yoshihisa Inoue, Taizo Yokoyama, and Akira Tai. "High photostationary state trans/cis ratios upon aromatic ester-sensitized photoisomerization of cyclooctene." Journal of Photochemistry and Photobiology A: Chemistry 48, no. 2-3 (1989): 465–67. http://dx.doi.org/10.1016/1010-6030(89)87024-8.

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