用于释放COS/HS的寡聚（硫代聚氨酯）的自增强解聚
Self-Amplified Depolymerization of Oligo(thiourethanes) for the Release of COS/HS.
作者信息
Powell Chadwick R, Foster Jeffrey C, Swilley Sarah N, Kaur Kuljeet, Scannelli Samantha J, Troya Diego, Matson John B
机构信息
Department of Chemistry, Virginia Tech Center for Drug Discovery Macromolecules Innovation Institute 1040 Drillfield Dr., Blacksburg, VA 24061.
出版信息
Polym Chem. 2019 Jun 21;10(23):2991-2995. doi: 10.1039/C9PY00354A. Epub 2019 Apr 24.
Abstract
Herein we report the self-amplified depolymerization of an aryl oligo(thiourethane) (OTU) for the release of COS/HS. The OTU was synthesized via polyaddition of 4-isothiocyanatobenzyl alcohol and end-capped with an aryl azide. The aryl azide chain-end was reduced by tris(2-carboxyethyl)phosphine or HS to the corresponding aniline, resulting in depolymerization (i.e., self-immolation) and the release of COS/HS. Depolymerization was monitored by H NMR and UV-Vis spectroscopy, and the released COS was converted into HS by the ubiquitous enzyme carbonic anhydrase in aqueous media.
摘要
在此，我们报道了一种芳基低聚（硫代聚氨酯）（OTU）的自增强解聚反应，用于释放COS/HS。OTU通过4-异硫氰酸苄醇的加成聚合反应合成，并以芳基叠氮化物封端。芳基叠氮链端被三（2-羧乙基）膦或HS还原为相应的苯胺，导致解聚（即自牺牲）并释放COS/HS。通过核磁共振氢谱（1H NMR）和紫外可见光谱监测解聚过程，并且在水性介质中，释放出的COS被普遍存在的碳酸酐酶转化为HS。
相似文献
1
Self-Amplified Depolymerization of Oligo(thiourethanes) for the Release of COS/HS.
Polym Chem. 2019 Jun 21;10(23):2991-2995. doi: 10.1039/C9PY00354A. Epub 2019 Apr 24.
2
Investigations into the carbonic anhydrase inhibition of COS-releasing donor core motifs.
Biochem Pharmacol. 2018 Mar;149:124-130. doi: 10.1016/j.bcp.2017.11.004. Epub 2017 Nov 10.
3
Cell-Membrane Coated Self-Immolative Poly(thiourethane) for Cysteine/Homocysteine-Triggered Intracellular HS Delivery.
ACS Macro Lett. 2023 Nov 21;12(11):1583-1588. doi: 10.1021/acsmacrolett.3c00558. Epub 2023 Nov 8.
4
Esterase-Triggered Self-Immolative Thiocarbamates Provide Insights into COS Cytotoxicity.
ACS Chem Biol. 2019 Feb 15;14(2):170-175. doi: 10.1021/acschembio.8b00981. Epub 2019 Jan 17.
5
Development of Acid-Mediated HS/COS Donors That Respond to a Specific pH Window.
J Org Chem. 2019 Nov 15;84(22):14469-14475. doi: 10.1021/acs.joc.9b01873. Epub 2019 Sep 18.
6
Reactive oxygen species-triggered off-on fluorescence donor for imaging hydrogen sulfide delivery in living cells.
Chem Sci. 2019 Jul 10;10(33):7690-7694. doi: 10.1039/c9sc02323b. eCollection 2019 Sep 7.
7
Therapeutic Delivery of HS via COS: Small Molecule and Polymeric Donors with Benign Byproducts.
J Am Chem Soc. 2016 Oct 19;138(41):13477-13480. doi: 10.1021/jacs.6b07204. Epub 2016 Oct 7.
8
Bio-orthogonal "click-and-release" donation of caged carbonyl sulfide (COS) and hydrogen sulfide (HS).
Chem Commun (Camb). 2017 Jan 24;53(8):1378-1380. doi: 10.1039/c6cc09547j.
9
Cysteine-activated hydrogen sulfide (HS) delivery through caged carbonyl sulfide (COS) donor motifs.
Chem Commun (Camb). 2018 May 10;54(39):4951-4954. doi: 10.1039/c8cc02428f.
10
Self-Immolative Thiocarbamates Provide Access to Triggered H2S Donors and Analyte Replacement Fluorescent Probes.
J Am Chem Soc. 2016 Jun 15;138(23):7256-9. doi: 10.1021/jacs.6b03780. Epub 2016 Jun 3.
引用本文的文献
1
Self-immolative poly(thiocarbamate) with localized HS signal amplification for precise cancer imaging and therapy.
Nat Commun. 2024 Aug 30;15(1):7558. doi: 10.1038/s41467-024-52006-0.
2
Emerging Trends in the Chemistry of End-to-End Depolymerization.
JACS Au. 2023 Aug 23;3(9):2436-2450. doi: 10.1021/jacsau.3c00345. eCollection 2023 Sep 25.
3
Intelligent polymeric hydrogen sulfide delivery systems for therapeutic applications.
Bioact Mater. 2022 Apr 13;19:198-216. doi: 10.1016/j.bioactmat.2022.03.043. eCollection 2023 Jan.
4
Self-Immolative Polymers: An Emerging Class of Degradable Materials with Distinct Disassembly Profiles.
J Am Chem Soc. 2021 Dec 22;143(50):21177-21188. doi: 10.1021/jacs.1c11410. Epub 2021 Dec 13.
5
Moving Past Quinone-Methides: Recent Advances Toward Minimizing Electrophilic Byproducts from COS/HS Donors.
Curr Top Med Chem. 2021;21(32):2882-2889. doi: 10.2174/1568026621666210622130002.
6
Targeted Delivery of Persulfides to the Gut: Effects on the Microbiome.
Angew Chem Int Ed Engl. 2021 Mar 8;60(11):6061-6067. doi: 10.1002/anie.202014052. Epub 2021 Jan 29.
7
Fluorescent labeling of plasmid DNA for gene delivery: Implications of dye hydrophobicity on labeling efficiencies and nanoparticle size.
Anal Biochem. 2022 May 1;644:113895. doi: 10.1016/j.ab.2020.113895. Epub 2020 Aug 9.
8
Use of Dithiasuccinoyl-Caged Amines Enables COS/H S Release Lacking Electrophilic Byproducts.
Chemistry. 2020 Apr 24;26(24):5374-5380. doi: 10.1002/chem.201905577. Epub 2020 Mar 4.
9
The Benefits of Macromolecular/Supramolecular Approaches in Hydrogen Sulfide Delivery: A Review of Polymeric and Self-Assembled Hydrogen Sulfide Donors.
Antioxid Redox Signal. 2020 Jan 10;32(2):79-95. doi: 10.1089/ars.2019.7864.
本文引用的文献
1
Self-Propagating Amplification Reactions for Molecular Detection and Signal Amplification: Advantages, Pitfalls, and Challenges.
J Phys Org Chem. 2018 Aug;31(8). doi: 10.1002/poc.3827. Epub 2018 Mar 23.
2
Cysteine-activated hydrogen sulfide (HS) delivery through caged carbonyl sulfide (COS) donor motifs.
Chem Commun (Camb). 2018 May 10;54(39):4951-4954. doi: 10.1039/c8cc02428f.
3
A review of hydrogen sulfide (HS) donors: Chemistry and potential therapeutic applications.
Biochem Pharmacol. 2018 Mar;149:110-123. doi: 10.1016/j.bcp.2017.11.014. Epub 2017 Nov 23.
4
Kinetic Insights into Hydrogen Sulfide Delivery from Caged-Carbonyl Sulfide Isomeric Donor Platforms.
J Am Chem Soc. 2017 Nov 15;139(45):16365-16376. doi: 10.1021/jacs.7b09527. Epub 2017 Nov 2.
5
Triggered and Tunable Hydrogen Sulfide Release from Photogenerated Thiobenzaldehydes.
Chemistry. 2017 Aug 22;23(47):11294-11300. doi: 10.1002/chem.201701206. Epub 2017 Jul 27.
6
Light-Activated COS/HS Donation from Photocaged Thiocarbamates.
Org Lett. 2017 May 5;19(9):2278-2281. doi: 10.1021/acs.orglett.7b00808. Epub 2017 Apr 17.
7
Bio-orthogonal "click-and-release" donation of caged carbonyl sulfide (COS) and hydrogen sulfide (HS).
Chem Commun (Camb). 2017 Jan 24;53(8):1378-1380. doi: 10.1039/c6cc09547j.
8
Hydrogen Sulfide Donors Activated by Reactive Oxygen Species.
Angew Chem Int Ed Engl. 2016 Nov 14;55(47):14638-14642. doi: 10.1002/anie.201608052. Epub 2016 Oct 24.
9
Therapeutic Delivery of HS via COS: Small Molecule and Polymeric Donors with Benign Byproducts.
J Am Chem Soc. 2016 Oct 19;138(41):13477-13480. doi: 10.1021/jacs.6b07204. Epub 2016 Oct 7.
10
Self-Immolative Thiocarbamates Provide Access to Triggered H2S Donors and Analyte Replacement Fluorescent Probes.
J Am Chem Soc. 2016 Jun 15;138(23):7256-9. doi: 10.1021/jacs.6b03780. Epub 2016 Jun 3.
Zotero 插件