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
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 50 条
  • [1] Cysteine-Activated Hydrogen Sulfide (H2S) Donors
    Zhao, Yu
    Wang, Hua
    Xian, Ming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (01) : 15 - 17
  • [2] Colorimetric Carbonyl Sulfide (COS)/Hydrogen Sulfide (H2S) Donation from γ-Ketothiocarbamate Donor Motifs
    Zhao, Yu
    Steiger, Andrea K.
    Pluth, Michael D.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13101 - 13105
  • [3] Chemical tools for carbonyl sulfide (COS) and hydrogen sulfide (H2S) delivery
    Pluth, Michael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [4] Bio-orthogonal "click-and-release'' donation of caged carbonyl sulfide (COS) and hydrogen sulfide (H2S)
    Steiger, Andrea K.
    Yang, Yang
    Royzen, Maksim
    Pluth, Michael D.
    CHEMICAL COMMUNICATIONS, 2017, 53 (08) : 1378 - 1380
  • [5] Esterase Activated Carbonyl Sulfide/Hydrogen Sulfide (H2S) Donors
    Chauhan, Preeti
    Bora, Prerona
    Ravikumar, Govindan
    Jos, Swetha
    Chakrapani, Harinath
    ORGANIC LETTERS, 2017, 19 (01) : 62 - 65
  • [6] Kinetic Insights into Hydrogen Sulfide Delivery from Caged-Carbonyl Sulfide Isomeric Donor Platforms
    Zhao, Yu
    Henthorn, Hillary A.
    Pluth, Michael D.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (45) : 16365 - 16376
  • [7] A cysteine-activated fluorescent H2S donor for visualizing H2S release and alleviating cellular inflammation
    Wang, Nianwei
    Wang, Xuan
    Wang, Jicheng
    Ren, Yikun
    Hua, Huiming
    Li, Dahong
    CHEMICAL COMMUNICATIONS, 2024, 61 (02) : 266 - 269
  • [8] Calcium sulfide (CaS), a donor of hydrogen sulfide (H2S): A new antihypertensive drug?
    Li, Ya-Feng
    Mao, Chuan-Shi
    Hui, Ru-Tai
    MEDICAL HYPOTHESES, 2009, 73 (03) : 445 - 447
  • [9] Visible-Light-Triggered Uncaging of Carbonyl Sulfide for Hydrogen Sulfide (H2S) Release
    Sharma, Ajay Kumar
    Nair, Mrutyunjay
    Chauhan, Preeti
    Gupta, Kavya
    Saini, Deepak K.
    Chakrapani, Harinath
    ORGANIC LETTERS, 2017, 19 (18) : 4822 - 4825
  • [10] Development and Application of Carbonyl Sulfide-Based Donors for H2S Delivery
    Levinn, Carolyn M.
    Cerda, Matthew M.
    Pluth, Michael D.
    ACCOUNTS OF CHEMICAL RESEARCH, 2019, 52 (09) : 2723 - 2731