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Journal articles on the topic 'Cyclooctane Series'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Sedenkova, Kseniya N., Olga V. Ryzhikova, Svetlana A. Stepanova, et al. "Bis(oxiranes) Containing Cyclooctane Core: Synthesis and Reactivity towards NaN3." Molecules 27, no. 20 (2022): 6889. http://dx.doi.org/10.3390/molecules27206889.

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Reactions of oxirane ring opening provide a powerful tool for regio- and stereoselective synthesis of polyfunctional and heterocyclic compounds, widely used in organic chemistry and drug design. Cyclooctane, alongside other medium-sized rings, is of interest as a novel molecular platform for the construction of target-oriented leads. Additionally, cyclooctane derivatives are well known to be prone to transannular reactions, which makes them a promising object in the search for novel approaches to polycyclic structures. In the present work, a series of cyclooctanediones was studied in Corey-Cha

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2

Ryzhikova, Olga V., Kseniya N. Sedenkova, Sergey V. Kositov, Victor A. Tafeenko, Yuri K. Grishin, and Elena B. Averina. "Stereoselective Approach to Hydroxyalkyl-1,2,3-triazoles Containing Cyclooctane Core and Their Use for CuAAC Catalysis." Catalysts 13, no. 5 (2023): 835. http://dx.doi.org/10.3390/catal13050835.

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1,2,3-Triazoles bearing additional functional groups have found applications as the ligands in catalysis of a broad scope of reactions, synthesis of transition metals complexes for various practicable purposes, and design of metal-based drugs. Triazolyl ligands accelerating CuAAC reactions, such as TBTA and TTTA, are nowadays commonly used in organic synthesis, and the search for novel ligands with a less complicated structure represents an important task. In the present work a series of hydroxyalkyltriazoles, containing a cyclooctane core, were synthesized via cycloaddition of readily availab

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3

Sedenkova, Kseniya N., Kristian S. Andriasov, Marina G. Eremenko, et al. "Bicyclic Isoxazoline Derivatives: Synthesis and Evaluation of Biological Activity." Molecules 27, no. 11 (2022): 3546. http://dx.doi.org/10.3390/molecules27113546.

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The application of non-planar scaffolds in drug design allows for the enlargement of the chemical space, and for the construction of molecules that have more effective target–ligand interactions or are less prone to the development of resistance. Among the works of the last decade, a literature search revealed spirothiazamenthane, which has served as a lead in the development of derivatives active against resistant viral strains. In this work, we studied the novel molecular scaffold, which resembles spirothiazamenthane, but combines isoxazoline as a heterocycle and cyclooctane ring as a hydrop

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4

Sedenkova, Kseniya N., Artem S. Sazonov, Dmitry A. Vasilenko, et al. "3-[N,N-Bis(sulfonyl)amino]isoxazolines with Spiro-Annulated or 1,2-Annulated Cyclooctane Rings Inhibit Reproduction of Tick-Borne Encephalitis, Yellow Fever, and West Nile Viruses." International Journal of Molecular Sciences 24, no. 13 (2023): 10758. http://dx.doi.org/10.3390/ijms241310758.

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Spirocyclic compounds containing heterocyclic moieties represent promising 3D scaffolds for modern drug design. In the search for novel anti-flaviviral agents, we have obtained a series of 3-[N,N-bis(sulfonyl)amino]isoxazolines containing spiro-annulated cyclooctane rings and assessed their antiviral activity against tick-borne encephalitis (TBEV), yellow fever (YFV), and West Nile (WNV) viruses. The structural analogs of spirocyclic compounds with a single sulfonyl group or 1,2-annulated cyclooctane ring were also investigated. Almost all the studied 3-[N,N-bis(sulfonyl)amino]isoxazolines rev

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5

Alleman, Cécile, Charlène Gadais, Laurent Legentil, and François-Hugues Porée. "Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series." Beilstein Journal of Organic Chemistry 19 (March 3, 2023): 245–81. http://dx.doi.org/10.3762/bjoc.19.23.

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Terpene compounds probably represent the most diversified class of secondary metabolites. Some classes of terpenes, mainly diterpenes (C20) and sesterterpenes (C25) and to a lesser extent sesquiterpenes (C15), share a common bicyclo[3.6.0]undecane core which is characterized by the presence of a cyclooctane ring fused to a cyclopentane ring, i.e., a [5-8] bicyclic ring system. This review focuses on the different strategies elaborated to construct this [5-8] bicyclic ring system and their application in the total synthesis of terpenes over the last two decades. The overall approaches involve t

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6

Kirillova, Marina V., Polyana Tomé de Paiva, Wagner A. Carvalho, Dalmo Mandelli, and Alexander M. Kirillov. "Mixed-ligand aminoalcohol-dicarboxylate copper(II) coordination polymers as catalysts for the oxidative functionalization of cyclic alkanes and alkenes." Pure and Applied Chemistry 89, no. 1 (2017): 61–73. http://dx.doi.org/10.1515/pac-2016-1012.

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AbstractNew copper(II) catalytic systems for the mild oxidative C–H functionalization of cycloalkanes and cycloalkenes were developed, which are based on a series of mixed-ligand aminoalcohol-dicarboxylate coordination polymers, namely [Cu2(μ-dmea)2(μ-nda)(H2O)2]n·2nH2O (1), [Cu2(μ-Hmdea)2(μ-nda)]n·2nH2O (2), and [Cu2(μ-Hbdea)2(μ-nda)]n·2nH2O (3) that bear slightly different dicopper(II) aminoalcoholate cores, as well as on a structurally distinct dicopper(II) [Cu2(H4etda)2(μ-nda)]·nda·4H2O (4) derivative [abbreviations: H2nda, 2,6-naphthalenedicarboxylic acid; Hdmea, N,N′-dimethylethanolamine

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7

Brodnik, Helena, Luka Ciber, Uroš Grošelj, Nejc Petek, Bogdan Štefane та Jurij Svete. "Preparation and Transformations of Acetophenone-Derived Enamino Ketones, BF2-β-Ketoiminates, and BF2-β-Diketonates". Molecules 30, № 3 (2025): 601. https://doi.org/10.3390/molecules30030601.

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A series of differently substituted β-enaminones 2a,b, 4a–i, 8a–d, and 9–13, their BF2-β-ketoiminate complexes 5a–d, and BF2-β-diketonate complexes 6a–d were prepared as model substrates for photochemical transformations. The attempted photochemical transformations of enaminones 2, 4, 8 and BF2-β-ketoiminate complexes 5 failed. On the other hand, irradiation of mixtures of BF2-β-diketonate complexes 6a–d and cycloalkanes with UV-A light (365 nm) gave the corresponding De Mayo reaction products 7a–f in 9–30% yields. The photochemical ring-expansion of acetyl tetralone-derived BF2-complex 6d gav

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8

Khaziev, Rail, Nikita Shtyrlin, Roman Pavelyev, et al. "Synthesis and Antimicrobial Activity of Adamantyl Substituted Pyridoxine Derivatives." Letters in Drug Design & Discovery 16, no. 12 (2019): 1360–69. http://dx.doi.org/10.2174/1570180816666190911150705.

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Background: Adamantane derivatives possess multiple pharmacological activities such as antiviral, anticancer, antimycobacterial, antidiabetic, antiparkinsonian and others. The interest of medicinal chemists in adamantane compounds is due to their unique spatial structure, high lipophilicity, and carbon cage rigidity. As a result, these molecules can easily penetrate biological lipid membranes and often have unique target-specific activity profile. Another pharmacophore studied in this work is pyridoxine (vitamin B6). Pyridoxine plays highly important roles in living cells as a key cofactor of

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9

Chung, Suhman, Michaela Wendeler, Jason W. Rausch, et al. "Structure-Activity Analysis of Vinylogous Urea Inhibitors of Human Immunodeficiency Virus-Encoded Ribonuclease H." Antimicrobial Agents and Chemotherapy 54, no. 9 (2010): 3913–21. http://dx.doi.org/10.1128/aac.00434-10.

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ABSTRACT Vinylogous ureas 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide and N-[3-(aminocarbonyl)-4,5-dimethyl-2-thienyl]-2-furancarboxamide (compounds 1 and 2, respectively) were recently identified to be modestly potent inhibitors of the RNase H activity of HIV-1 and HIV-2 reverse transcriptase (RT). Both compounds shared a 3-CONH2-substituted thiophene ring but were otherwise structurally unrelated, which prevented a precise definition of the pharmacophore. We have therefore examined a larger series of vinylogous ureas carrying amide, amine, and cycloalkane modifications

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10

Wang, Huiqun, Sebla Onbulak, Steven Weigand, Frank S. Bates, and Marc A. Hillmyer. "Polyolefin graft copolymers through a ring-opening metathesis grafting through approach." Polymer Chemistry 12, no. 14 (2021): 2075–83. http://dx.doi.org/10.1039/d0py01728k.

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A series of polyethylene-g-atactic polypropylene graft copolymers were synthesized by grafting through copolymerization of a cyclooctene terminated aPP macromonomer with cyclooctene monomer and subsequent hydrogenation.

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11

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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12

Zhou, Zhe, Cansu Ergene, and Edmund F. Palermo. "Synthetic mimics of cyclic antimicrobial peptides via templated ring-opening metathesis (TROM)." Polymer Chemistry 10, no. 43 (2019): 5849–58. http://dx.doi.org/10.1039/c9py01271k.

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We utilized a templated ring-opening metathesis (TROM) strategy to synthesize a series of precision macrocyclic olefins, each containing two, three or four repeating units of a cyclooctene with pendant carboxylic acid side chains.

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13

Mandarić, Mirna, Edi Topić, Dominique Agustin, Jana Pisk, and Višnja Vrdoljak. "Preparative and Catalytic Properties of MoVI Mononuclear and Metallosupramolecular Coordination Assemblies Bearing Hydrazonato Ligands." International Journal of Molecular Sciences 25, no. 3 (2024): 1503. http://dx.doi.org/10.3390/ijms25031503.

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A series of polynuclear, dinuclear, and mononuclear Mo(VI) complexes were synthesized with the hydrazonato ligands derived from 5-methoxysalicylaldehyde and the corresponding hydrazides (isonicotinic hydrazide (H2L1), nicotinic hydrazide (H2L2), 2-aminobenzhydrazide (H2L3), or 4-aminobenzhydrazide (H2L4)). The metallosupramolecular compounds obtained from non-coordinating solvents, [MoO2(L1,2)]n (1 and 2) and [MoO2(L3,4)]2 (3 and 4), formed infinite structures and metallacycles, respectively. By blocking two coordination sites with cis-dioxo ligands, the molybdenum centers have three coordinat

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14

Zedník, Jiří, Jan Sedláček, Jan Svoboda, Jiří Vohlídal, Dmitrij Bondarev та Ivana Císařová. "Bis(μ-carboxylato)dienerhodium(I) Complexes - Synthesis, Characterization and Catalytic Activity". Collection of Czechoslovak Chemical Communications 73, № 8-9 (2008): 1205–21. http://dx.doi.org/10.1135/cccc20081205.

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Dinuclear rhodium(I) η2:η2-cycloocta-1,5-diene (series a) and η2:η2-norborna-2,5-diene (series b) complexes with μ-RCOO- ligands, where R is linear C21H43 (complexes 1a, 1b), CH2CMe3 (2a, 2b), 1-adamantyl (3a, 3b) and benzyl (4a, 4b), have been prepared and characterized by spectroscopic methods. Structures of complexes 2b, 3a and 4a were determined by X-ray diffraction analysis. Complexes prepared show low to moderate catalytic activity in polymerization of phenylacetylene in THF giving high-cis-transoid polymers, but they show only oligomerization activity in dichloromethane.

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15

Saadi, Jakub, Irene Brüdgam, and Hans-Ulrich Reissig. "Highly substituted benzannulated cyclooctanol derivatives by samarium diiodide-induced cyclizations." Beilstein Journal of Organic Chemistry 6 (December 28, 2010): 1229–45. http://dx.doi.org/10.3762/bjoc.6.141.

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A series of γ-oxo esters suitably substituted with various styrene subunits was subjected to samarium diiodide-induced 8-endo-trig cyclizations. Efficacy, regioselectivity and stereoselectivity of these reactions via samarium ketyls strongly depend on the substitution pattern of the attacked alkene moiety. The stereoselectivity of the protonation of the intermediate samariumorganyl is also influenced by the structural features of the substrates. This systematic study reveals that steric and electronic factors exhibited by the alkene and ketone subunits are of high importance for the outcome of

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16

Hasanzadeh Esfahani, Maryam, Mahdi Behzad, Michal Dusek, and Monika Kucerakova. "Synthesis and characterization of a series of acylpyrazolone transition metal complexes: Crystal structures and catalytic performance in the epoxidation of cyclooctene." Inorganica Chimica Acta 508 (August 2020): 119637. http://dx.doi.org/10.1016/j.ica.2020.119637.

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17

Chowdhury, Habibar, Rajesh Bera, and Chandan Adhikary. "Synthesis, Structure, Magnetic and Catalytic Competency of a Tetradentate (NNOO) Schiff Base Mediated Dimeric Copper(II) Complex." Asian Journal of Chemistry 33, no. 6 (2021): 1280–86. http://dx.doi.org/10.14233/ajchem.2021.23168.

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One dinuclear copper(II) complex {μ-[2,2′-{ethane-1,2-diylbis[(azanylylidene)methanylylidene]}- bis(phenolato)]}-{μ-[2,2′-{ethane-1,2-diylbis[(azanylylidene)methanylylidene]}bis(phenolato)]}- dicopper(II), [Cu2(salen)2] (1) [salen2− = [2,2′-{ethane-1,2-diylbis[(azanylylidene)methanylylidene]}- bis(phenolato)] has been isolated and characterized by X-ray diffraction analysis and spectroscopic studies. X-ray single crystal structure examination revealed that each Cu(II) center in the asymmetric unit of 1 adopts a distorted square planar geometry with a CuN2O2 chromophore, where two asymmetric un

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18

Štěpnička, Petr, and Ivana Císařová. "Synthesis and Coordination Behaviour of a Phosphanyl(vinyl)ferrocene." Collection of Czechoslovak Chemical Communications 71, no. 2 (2006): 215–36. http://dx.doi.org/10.1135/cccc20060215.

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Donor properties of 1-(diphenylphosphanyl)-1'-vinylferrocene (1) were investigated in a series of reactions with palladium(II), rhodium(I), and copper(I) compounds. In all complexes obtained, compound 1 coordinates exclusively as a monodentate phosphorus donor, giving trans-[PdCl2(1-κP)2] (3) with [PdCl2(cod)], [PdCl(LNC)(1-κP)] (4) with [{Pd(LNC)}2(μ-Cl)2], and trans-[RhCl(CO)(1-κP)2] (5) with [{Rh(CO)2}2(μ-Cl)2] (cod = cycloocta-1,5-diene, LNC = 2-[(dimethylamino)methyl-κN]phenyl-κC1). Copper(I) precursors CuI and [Cu(MeCN)4]PF6 reacted with 1 in a similar manner, yielding at appropriate mol

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19

Enriquez, Raul G., Juan M. Fernandez-G, Ismael Leon, William F. Reynolds, Ji Ping Yang, and Margaret Yu. "Investigation of the effect of ring size on the product distribution for the Schiff base reaction of 2-acetylcycloalkanones with diamino alkanes." Canadian Journal of Chemistry 73, no. 1 (1995): 16–21. http://dx.doi.org/10.1139/v95-004.

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The Schiff base condensation reaction of 1,2-diaminoethane with a series of 2-acetylcycloalkanones (from cyclopentanone to cyclooctanone) has been investigated and the products characterized by two-dimensional nuclear magnetic resonance. The site of attack of the amino groups, i.e., ring ketone or acetyl ketone, is determined primarily by ring size. 2-Acetylcyclohexanone yields two products in ca. 9:1 ratio, the major product where the two amino groups attack at the ring ketones of two different cyclohexanone molecules, and the minor product where one amino group attacks one ring carbonyl of o

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20

Adjieufack, Abel Idrice, Jean Moto Ongagna, Jean Serge Essomba, et al. "Exploring the Mechanism of the Intramolecular Diels–Alder Reaction of (2E,4Z,6Z)-2(allyloxy)cycloocta-2,4,6-trien-1-one Using Bonding Evolution Theory." Molecules 28, no. 19 (2023): 6755. http://dx.doi.org/10.3390/molecules28196755.

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In the present work, the bond breaking/forming events along the intramolecular Diels–Alder (IMDA) reaction of (2E,4Z,6Z)-2(allyloxy)cycloocta-2,4,6-trien-1-one have been revealed within bonding evolution theory (BET) at the density functional theory level, using the M05-2X functional with the cc-pVTZ basis set. Prior to achieving this task, the energy profiles and stationary points at the potential energy surface (PES) have been characterized. The analysis of the results finds that this rearrangement can proceed along three alternative reaction pathways (a–c). Paths a and b involve two steps,

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21

Cáceres-Alonso, Mercedes, Miguel Costas, Lina Andreoli-Ball, and Donald Patterson. "Steric effects on the self-association of branched and cyclic alcohols in inert solvents. Apparent heat capacities of secondary and tertiary alcohols in hydrocarbons." Canadian Journal of Chemistry 66, no. 4 (1988): 989–98. http://dx.doi.org/10.1139/v88-165.

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Apparent heat capacities have been measured for fifteen branched and cyclic alcohols in dilute n-decane solution at 25 °C. The alcohols were 2-methyl-2-propanol, cyclohexanol, 3-methyl-3-pentanol, trans-, cis-, and mixed isomer 2-methylcyclohexanol, 1-methylcyclohexanol, 3-ethyl-3-pentanol, cyclooctanol, 3,7-dimethyl-1-octanol, 5-decanol, 4-propyl-4-heptanol, cyclododecanol, 5-butyl-5-nonanol, and 8-hexadecanol (in n-hexane). Excess heat capacities CpE throughout the concentration range were measured at 25 °C for: 1-hexanol + n-hexadecane (n-C16) and + 2,2,4,4,6,8,8-heptamethylnonane (br-C16),

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22

McFarland, Jesse M., Masa Aleckovic, George Coricor, et al. "Abstract 1540: A click chemistry-activated auristatin protodrug (TCO-MMAE) demonstrates potency and safety with antibody and intratumoral tumor-targeting agents." Cancer Research 83, no. 7_Supplement (2023): 1540. http://dx.doi.org/10.1158/1538-7445.am2023-1540.

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Abstract Click chemistry encompasses chemical reactions that are highly efficient, rapid and proceed in complex environments. The 2022 Nobel prize in Chemistry was awarded to Sharpless, Meldal and Bertozzi in recognition of the transformative effect click chemistry has had in research and drug development. Using click chemistry to precisely control the activation of drugs at tumors, Shasqi has developed the Click Activated Protodrugs Against Cancer (CAPAC™) platform. In essence, a click chemistry activator is localized to tumors, which subsequently activates protodrug(s) bearing the companion

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23

Li, Jiahui, Michael Thomas Gambles, Shannuo Li, Jindřich Kopeček, Douglas Sborov, and Jiyuan Yang. "Development of Next Generation Antibody-Polymer-Drug Conjugates for Treatment of Multiple Myeloma." Blood 142, Supplement 1 (2023): 3308. http://dx.doi.org/10.1182/blood-2023-186661.

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Background: Antibody-drug conjugates (ADCs) are an effective class of cancer therapeutics, but current ADCs face stability challenges, resulting in premature payload release and off-target toxicity. To overcome this, we developed a novel strategy using antibody-polymer-based drug conjugates (pADCs). Our pADCs have a number of advantages compared to currently FDA approved ADCs, including: 1) Increased drug payload without altering binding site numbers, ensuring maximum drug loading without affecting antigen and Fc binding; 2) Potential for synergistic immunotherapy and chemotherapy; 3) Improved

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24

Jing, Liang, Shamaila Yousaf, Saira Farhad, Fairouz Tchier, and Adnan Aslam. "Analyzing the expected values of neighborhood degree-based topological indices in random cyclooctane chains." Frontiers in Chemistry 12 (April 26, 2024). http://dx.doi.org/10.3389/fchem.2024.1388097.

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Cyclooctane is classified as a cycloalkane, characterized by the chemical formula C8H16. It consists of a closed ring structure composed of eight carbon atoms and sixteen hydrogen atoms. A cyclooctane chain typically refers to a series of cyclooctane molecules linked together. Cyclooctane and its derivatives find various applications in chemistry, materials science, and industry. Topological indices are numerical values associated with the molecular graph of a chemical compound, predicting certain physical or chemical properties. In this study, we calculated the expected values of degree-based

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25

Ryzhikova, Olga V., Aleksandra S. Churkina, Kseniya N. Sedenkova, et al. "Mono‐ and bis(steroids) containing a cyclooctane core: Synthesis, antiproliferative activity, and action on cell cytoskeleton microtubules." Archiv der Pharmazie, July 30, 2024. http://dx.doi.org/10.1002/ardp.202400483.

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AbstractSteroid dimers of natural and synthetic origin possess an unusual and complex molecular architecture that may lead to the realization of peculiar effects in biological systems, in particular in different cancer cell lines. In the present work, diastereoselective ring‐opening of mono‐ and polyoxiranes, containing a cyclooctane core, by azide‐anion was performed to yield a series of azidoalcohols with different types of symmetry. The products were involved in copper‐catalyzed azyde‐alkyne cycloaddition (CuAAC) reaction with ethinylestradiol and ethinyltestosterone, and the resulting ster

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26

GAUTAM, R. K., S. KANNAN, G. S. SAHARIA, and M. P. TYAGI. "ChemInform Abstract: Studies in the Cyclooctane Series. Part 9. Friedel-Crafts Reaction of the Anhydride of 1-Carboxycyclooctane-1-acetic Acid with Some Aromatic Substrates and Synthesis of 2,3-Benzo-Substituted Benzospiro(5,7)tridecanes." ChemInform 21, no. 31 (1990). http://dx.doi.org/10.1002/chin.199031137.

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27

Cokoja, Mirza, Fabian Schmidt, Markus Drees, Markus Hegelmann, Bastian Zehner, and Andreas Jess. "Surface‐Active Imidazolium Diorganophosphates as Catalysts for Epoxidations in Water." European Journal of Inorganic Chemistry, April 9, 2025. https://doi.org/10.1002/ejic.202500071.

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The synthesis and characterization of a series of imidazolium diorganophosphate‐based surface‐active ionic liquids (SAILs) of the general formula [OMIm][(RO)2PO2] (OMIm = 1‐octyl‐3‐methylimidazolium; R = H, Me, Et, Ph, p‐MeOPh) is reported. The reaction of [OMIm][(RO)2PO2] SAILs with hydrogen peroxide was investigated via 31P‐NMR spectroscopy, showing the presence of a phosphorous‐peroxo product, which was corroborated by DFT calculations. The sizes of the SAIL micelles in aqueous hydrogen peroxide were investigated by dynamic light scattering (DLS) before and after addition of cis‐cyclooctene

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28

Morrill, Kaitlyn, Jason D. Josephson, Didier A. Bilodeau, Baha Altamimi, Masaya Nakajima, and John Paul Pezacki. "Bioorthogonal Reactions of Oxadiazinones With Strained trans‐Cyclooctenes." Journal of Physical Organic Chemistry 38, no. 2 (2024). https://doi.org/10.1002/poc.4674.

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ABSTRACTWe report quantitative details of addition reactions of a strained trans‐cyclooctene with a series of oxadiazinones, analogues of the bioorthogonally fruitful tetrazines. Both experimental and computational studies of these ligations reveal their sensitivity to differing electronic character of oxadiazinone substituents. Achieving rate constants up to 9.5 L mol−1 s−1, oxadiazinones demonstrate untapped potential for bioorthogonal applications.

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29

Kim, Dahham, Hayoung Son, and Seung Bum Park. "Ultrafluorogenic Monochromophore‐Type BODIPY‐Tetrazine Series for Dual‐Color Bioorthogonal Imaging with a Single Probe." Angewandte Chemie, September 25, 2023. http://dx.doi.org/10.1002/ange.202310665.

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Various fluorogenic probes utilizing tetrazine (Tz) as a fluorescence quencher and bioorthogonal reaction partner have been extensively studied over the past few decades. Herein, we synthesized a series of boron‐dipyrromethene (BODIPY)‐Tz probes using monochromophoric design strategy for bioorthogonal cellular imaging. The BODIPY‐Tz probes exhibited excellent bicyclo[6.1.0]nonyne (BCN)‐selective fluorogenicity with three‐ to four‐digit‐fold enhancements in fluorescence over a wide range of emission wavelengths, including the far‐red region. Furthermore, we demonstrated the applicability of BOD

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30

Kim, Dahham, Hayoung Son, and Seung Bum Park. "Ultrafluorogenic Monochromophore‐Type BODIPY‐Tetrazine Series for Dual‐Color Bioorthogonal Imaging with a Single Probe." Angewandte Chemie International Edition, September 25, 2023. http://dx.doi.org/10.1002/anie.202310665.

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Various fluorogenic probes utilizing tetrazine (Tz) as a fluorescence quencher and bioorthogonal reaction partner have been extensively studied over the past few decades. Herein, we synthesized a series of boron‐dipyrromethene (BODIPY)‐Tz probes using monochromophoric design strategy for bioorthogonal cellular imaging. The BODIPY‐Tz probes exhibited excellent bicyclo[6.1.0]nonyne (BCN)‐selective fluorogenicity with three‐ to four‐digit‐fold enhancements in fluorescence over a wide range of emission wavelengths, including the far‐red region. Furthermore, we demonstrated the applicability of BOD

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31

Son, Hayoung, Dahham Kim, Sohee Kim, Wan Gi Byun, and Seung Bum Park. "Unveiling the Structure‐Fluorogenic Property Relationship of Seoul‐Fluor‐Derived Bioorthogonal Tetrazine Probes." Angewandte Chemie International Edition, November 29, 2024. http://dx.doi.org/10.1002/anie.202421982.

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Tetrazine (Tz)‐embedded fluorescent probes, known for their fluorogenicity following bioorthogonal inverse electron‐demand Diels‐Alder (iEDDA) reactions, are extensively used in bioimaging. Despite significant research on fluorogenic Tz probes, there has been limited systematic exploration of their fluorogenic responses with various dienophiles. In this study, we elucidate the structure‐fluorogenic property relationship of bioorthogonal Tz probes. We synthesized a series of Seoul‐Fluor‐Tz (SFTz) probes designed to exhibit differentiated turn‐on fluorescence upon iEDDA reactions with three dien

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Son, Hayoung, Dahham Kim, Sohee Kim, Wan Gi Byun, and Seung Bum Park. "Unveiling the Structure‐Fluorogenic Property Relationship of Seoul‐Fluor‐Derived Bioorthogonal Tetrazine Probes." Angewandte Chemie, November 29, 2024. http://dx.doi.org/10.1002/ange.202421982.

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Abstract:

Tetrazine (Tz)‐embedded fluorescent probes, known for their fluorogenicity following bioorthogonal inverse electron‐demand Diels‐Alder (iEDDA) reactions, are extensively used in bioimaging. Despite significant research on fluorogenic Tz probes, there has been limited systematic exploration of their fluorogenic responses with various dienophiles. In this study, we elucidate the structure‐fluorogenic property relationship of bioorthogonal Tz probes. We synthesized a series of Seoul‐Fluor‐Tz (SFTz) probes designed to exhibit differentiated turn‐on fluorescence upon iEDDA reactions with three dien

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Kardelis, Vladimir, Maria M. Denk, and Alex Adronov. "Click‐Functionalization of a Poly(Tetrazine)‐co‐Fluorene‐Conjugated Polymer with a Series of trans ‐Cyclooctene Derivatives." Angewandte Chemie International Edition, December 2020. http://dx.doi.org/10.1002/anie.202010795.

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Kardelis, Vladimir, Maria M. Denk, and Alex Adronov. "Click‐Functionalization of a Poly(Tetrazine)‐co‐Fluorene‐Conjugated Polymer with a Series of trans ‐Cyclooctene Derivatives." Angewandte Chemie International Edition, January 4, 2021. http://dx.doi.org/10.1002/anie.202016963.

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Kardelis, Vladimir, Maria M. Denk, and Alex Adronov. "Click‐Functionalization of a Poly(Tetrazine)‐co‐Fluorene‐Conjugated Polymer with a Series of trans ‐Cyclooctene Derivatives." Angewandte Chemie, December 2020. http://dx.doi.org/10.1002/ange.202010795.

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Kardelis, Vladimir, Maria M. Denk, and Alex Adronov. "Click‐Functionalization of a Poly(Tetrazine)‐co‐Fluorene‐Conjugated Polymer with a Series of trans ‐Cyclooctene Derivatives." Angewandte Chemie, January 4, 2021. http://dx.doi.org/10.1002/ange.202016963.

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Cano, Israel, Andreas Weilhard, Carmen Martin, et al. "Blurring the boundary between homogenous and heterogeneous catalysis using palladium nanoclusters with dynamic surfaces." Nature Communications 12, no. 1 (2021). http://dx.doi.org/10.1038/s41467-021-25263-6.

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AbstractUsing a magnetron sputtering approach that allows size-controlled formation of nanoclusters, we have created palladium nanoclusters that combine the features of both heterogeneous and homogeneous catalysts. Here we report the atomic structures and electronic environments of a series of metal nanoclusters in ionic liquids at different stages of formation, leading to the discovery of Pd nanoclusters with a core of ca. 2 nm surrounded by a diffuse dynamic shell of atoms in [C4C1Im][NTf2]. Comparison of the catalytic activity of Pd nanoclusters in alkene cyclopropanation reveals that the a

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Barrett, Khandra, Matthew Dupuis, Anna Crossman, et al. "Synthesis, characterization, and anticancer properties of iminopyridine platinum(II) complexes containing long aliphatic chains‡." Canadian Journal of Chemistry, June 30, 2023. http://dx.doi.org/10.1139/cjc-2023-0031.

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A series of iminopyridine ligands were prepared from the condensation reaction of 6-methylpyridine-2-carboxaldehyde and long chain aliphatic primary amines. Square planar platinum(II) complexes were synthesized from the reaction of [PtCl2(η2-coe)]2 (coe = cis-cyclooctene) with two equivalents of ligand. The synthesis of the platinum compounds appears to go through a 5-coordinate trigonal pyramidal species where coe remains coordinated initially but eventually dissociates to afford the 4-coordinate complexes. Ligands and platinum complexes were characterized using multi-nuclear NMR and FT-IR sp

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Ly, Alexandra L., and Alex Adronov. "Exploring the reactivity and interactions of a poly(fluorene‐co‐tetrazine)‐conjugated polymer with Single‐walled Carbon Nanotubes." Journal of Polymer Science, September 17, 2024. http://dx.doi.org/10.1002/pol.20240593.

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AbstractConjugated tetrazine‐containing polymers that undergo inverse electron demand Diels‐Alder (IEDDA) reactions with trans‐cyclooctenes are interesting not only for their intrinsic optoelectronic properties, but also their interactions with π‐conjugated surfaces. Here, we prepared a series of poly(fluorene‐co‐tetrazine) polymers and carried out IEDDA reactions to decorate them with hydroxyl, hexadecyl, or triethylene glycol side chains. The polymers were investigated pre‐ and post‐IEDDA coupling in terms of their ability to disperse single‐walled carbon nanotubes (SWNTs) in organic solvent

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Brind, Thomasin, Aggie Lawer, Tobias Todd, Sushant Aryal, Sarah Hook, and Allan Bernard Gamble. "Bioorthogonal Click‐to‐Release of Branched Pro‐Fluorophores." Chemistry – A European Journal, June 24, 2025. https://doi.org/10.1002/chem.202501544.

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Bioorthogonal click‐to‐release prodrug activation strategies should be fast and high yielding. However, in strain‐promoted alkene‐azide click‐to‐release, a fast click‐step translates to slow and inefficient drug release. To improve drug yield, branched dual‐core scaffolds that increase drug release are reported. The dual‐core consists of an exposed electron‐deficient aryl azide (core‐1) attached to an electron‐rich self‐immolating branched linker (core‐2). Core‐1, a tetrafluoroaryl azide with methyl‐substitution at the benzylic carbon, facilitates a rapid click reaction with trans‐cyclooctenes

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