Self-amplified depolymerization of oligo(thiourethanes) for the release of COS/H2S

被引:0
|
作者
Powell, Chadwick R. [1 ]
Foster, Jeffrey C. [1 ]
Swilley, Sarah N. [1 ]
Kaur, Kuljeet [1 ]
Scannelli, Samantha J. [1 ]
Troya, Diego [1 ]
Matson, John B. [1 ]
机构
[1] Virginia Tech, Ctr Drug Discovery, Macromol Innovat Inst, Dept Chem, 1040 Drillfield Dr, Blacksburg, VA 24061 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
HYDROGEN-SULFIDE; H2S DONORS; DELIVERY; PATHOGENESIS; DENDRIMERS; MOLECULE; DONATION; DESIGN; COS;
D O I
10.1039/c9py00354a
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Herein we report the self-amplified depolymerization of an aryl oligo(thiourethane) (OTU) for the release of COS/H2S. 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 H2S to the corresponding aniline, resulting in depolymerization (i.e., self-immolation) and the release of COS/H2S. Depolymerization was monitored by H-1 NMR and UV-Vis spectroscopy, and the released COS was converted into H2S by the ubiquitous enzyme carbonic anhydrase in aqueous media, generating an amplified response.
引用
收藏
页码:2991 / 2995
页数:5
相关论文
共 50 条
  • [1] Nanocoated bacteria with H2S generation-triggered self-amplified photothermal and photodynamic effect for breast cancer therapy
    Zhuang, He
    Wang, Rui
    Qi, Yao
    Liu, Yufei
    Xiong, Hui
    Yao, Jing
    JOURNAL OF CONTROLLED RELEASE, 2024, 373 : 507 - 519
  • [2] Use of Dithiasuccinoyl-Caged Amines Enables COS/H2S Release Lacking Electrophilic Byproducts
    Cerda, Matthew M.
    Mancuso, Jenna L.
    Mullen, Emma J.
    Hendon, Christopher H.
    Pluth, Michael D.
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (24) : 5374 - 5380
  • [3] Insights into the Mechanism of Thiol-Triggered COS/H2S Release from N-Dithiasuccinoyl Amines
    Zhou, Shengchao
    Mou, Yujie
    Liu, Miao
    Du, Qian
    Ali, Basharat
    Ramprasad, Jurupula
    Qiao, Chunhua
    Hu, Li-Fang
    Ji, Xingyue
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (13) : 8352 - 8359
  • [4] Simultaneous removal of H2S and COS using activated carbons and their supported catalysts
    Sakanishi, K
    Wu, ZH
    Matsumura, A
    Saito, I
    Hanaoka, T
    Minowa, T
    Tada, M
    Iwasaki, T
    CATALYSIS TODAY, 2005, 104 (01) : 94 - 100
  • [5] Inhibition of Mitochondrial Bioenergetics by Esterase-Triggered COS/H2S Donors
    Steiger, Andrea K.
    Marcatti, Michela
    Szabo, Csaba
    Szczesny, Bartosz
    Pluth, Michael D.
    ACS CHEMICAL BIOLOGY, 2017, 12 (08) : 2117 - 2123
  • [6] Light-Activated COS/H2S Donation from Photocaged Thiocarbamates
    Zhao, Yu
    Bolton, Sarah G.
    Pluth, Michael D.
    ORGANIC LETTERS, 2017, 19 (09) : 2278 - 2281
  • [7] Self-Assembled Nanostructures Regulate H2S Release from Constitutionally Isomeric Peptides
    Wang, Yin
    Kaur, Kuljeet
    Scannelli, Samantha J.
    Bitton, Ronit
    Matson, John B.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (44) : 14945 - 14951
  • [8] Amino acid-based H2S donors: N-thiocarboxyanhydrides that release H2S with innocuous byproducts
    Kaur, Kuljeet
    Enders, Patrick
    Zhu, Yumeng
    Bratton, Abigail F.
    Powell, Chadwick R.
    Kashfi, Khosrow
    Matson, John B.
    CHEMICAL COMMUNICATIONS, 2021, 57 (45) : 5522 - 5525
  • [9] Regulating H2S release from self-assembled peptide H2S-donor conjugates using cysteine derivatives
    Li, Zhao
    Thomas, Marius
    Berac, Christian M.
    Stach, Oliver S.
    Besenius, Pol
    Matson, John B.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (40) : 8173 - 8181
  • [10] H2S Activated Drug Release from Protein Cages
    Chen, Weijian
    Zhang, Yajie
    Li, Xiao
    Chen, Hong
    Sun, Jian
    Feng, Fude
    ACS APPLIED MATERIALS & INTERFACES, 2017, 9 (39) : 33571 - 33575