Cysteine-activated hydrogen sulfide (H2S) delivery through caged carbonyl sulfide (COS) donor motifs

被引：64
作者：
Zhao, Yu [1 ]
Steiger, Andrea K. [1 ]
Pluth, Michael D. [1 ]
机构：
[1] Univ Oregon, Inst Mol Biol, Mat Sci Inst, Dept Chem & Biochem, Eugene, OR 97403 USA
来源：
CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 39期
基金：
美国国家科学基金会;
关键词：
SULFUR-DIOXIDE SO2; FLUORESCENT-PROBES; RELEASE; AGENTS; HOMOCYSTEINE; INHIBITION; CHEMISTRY; DONATION;
D O I：
10.1039/c8cc02428f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Hydrogen sulfide (H2S) is an important biomolecule, and controllable H2S donors are needed to investigate H2S biological functions. Here we utilize cysteine-mediated addition/cyclization chemistry to unmask an acrylate-functionalized thiocarbamate and release carbonyl sulfide (COS), which is quickly converted to H2S by carbonic anhydrase (CA).
引用
收藏
页码：4951 / 4954
页数：4
相关论文
共 33 条
  • [1] Abe K, 1996, J NEUROSCI, V16, P1066
  • [2] SYNTHESIS OF SOME STABLE 7-HALO-1,4-THIAZEPINES - POTENTIAL SUBSTITUTED PENAM PRECURSORS
    BLONDEAU, P
    GAUTHIER, R
    BERSE, C
    GRAVEL, D
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (23): : 3866 - &
  • [3] Esterase Activated Carbonyl Sulfide/Hydrogen Sulfide (H2S) Donors
    Chauhan, Preeti
    Bora, Prerona
    Ravikumar, Govindan
    Jos, Swetha
    Chakrapani, Harinath
    [J]. ORGANIC LETTERS, 2017, 19 (01) : 62 - 65
  • [4] Thiol-Activated Anticancer Agents: The State of the Art
    Dalzoppo, Daniele
    Di Paolo, Veronica
    Calderan, Laura
    Pasut, Gianfranco
    Rosato, Antonio
    Caccuri, Anna Maria
    Quintieri, Luigi
    [J]. ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2017, 17 (01) : 4 - 20
  • [5] Chemical Biology of H2S Signaling through Persulfidation
    Filipovic, Milos R.
    Zivanovic, Jasmina
    Alvarez, Beatriz
    Banerjee, Ruma
    [J]. CHEMICAL REVIEWS, 2018, 118 (03) : 377 - 461
  • [6] A practical guide to working with H2S at the interface of chemistry and biology
    Hartle, Matthew D.
    Pluth, Michael D.
    [J]. CHEMICAL SOCIETY REVIEWS, 2016, 45 (22) : 6108 - 6117
  • [7] SYNTHESIS AND STEREOCHEMISTRY OF SUBSTITUTED 1,4-THIAZEPINES RELATED TO PENICILLINS
    LEONARD, NJ
    NING, RY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) : 3928 - &
  • [8] Cell-trappable fluorescent probes for endogenous hydrogen sulfide signaling and imaging H2O2-dependent H2S production
    Lin, Vivian S.
    Lippert, Alexander R.
    Chang, Christopher J.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2013, 110 (18) : 7131 - 7135
  • [9] Design, Synthesis, and Evaluation of Thiol-Activated Sources of Sulfur Dioxide (SO2) as Antimycobacterial Agents
    Malwal, Satish R.
    Sriram, Dharmarajan
    Yogeeswari, Perumal
    Konkimalla, V. Badireenath
    Chakrapani, Harinath
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (01) : 553 - 557
  • [10] Cascade Reaction-Based, Near-Infrared Multiphoton Fluorescent Probe for the Selective Detection of Cysteine
    Nawimanage, Rasika R.
    Prasai, Bijeta
    Hettiarachchi, Suraj U.
    McCarley, Robin L.
    [J]. ANALYTICAL CHEMISTRY, 2017, 89 (12) : 6886 - 6892
1234