• 中国精品科技期刊
  • 中国高校百佳科技期刊
  • 中国中文核心期刊
  • 中国科学引文数据库核心期刊
Advanced Search
SHEN Xinxin, ZHANG Yihua, HUANG Zhangjian. Research advances in hydrogen sulfide donors[J]. Journal of China Pharmaceutical University, 2019, 50(3): 265-272. DOI: 10.11665/j.issn.1000-5048.20190302
Citation: SHEN Xinxin, ZHANG Yihua, HUANG Zhangjian. Research advances in hydrogen sulfide donors[J]. Journal of China Pharmaceutical University, 2019, 50(3): 265-272. DOI: 10.11665/j.issn.1000-5048.20190302

Research advances in hydrogen sulfide donors

More Information
  • Hydrogen sulfide(H2S)is an endogenous gas messenger molecule with extremely broad biological activities including vasodilation, anti-oxidation, anti-inflammation, cardioprotection and anti-tumor. Similar to other gas messenger molecules, the biological activity of H2S is dependent on its location, concentration and duration of exposure. Therefore, the key scientific issue is how to improve the selectivity of H2S donor molecules to release appropriate concentrations of H2S at the target site(commonly pathological place), exerting therapeutic efficacy with limited side-effects. This article reviews the structures and H2S release mechanisms of two classes of H2S donors focusing on the advances in the recently developed H2S donors with controllable release potential of H2S, thus providing new ideas for future H2S-based drug research.
  • [1]
    Abe K, Kimura H. The possible role of hydrogen sulfide as an endogenous neuromodulator[J].J Neurosci,1996,16(3):1066-1071.
    [2]
    Wang R.Two′s company,three′s a crowd:can H2S be the third endogenous gaseous transmitter[J].FASEB J,2002,16(13):1792-1798.
    [3]
    Kamoun P.Endogenous production of hydrogen sulfide in mammals[J].Amino Acids,2004,26(3):243-254.
    [4]
    Mikami Y,Shibuya N,Kimura Y,et al.Thioredoxin and dihydrolipoic acid are required for 3-mercaptopyruvate sulfurtransferase to produce hydrogen sulfide[J].Biochem J,2011,439(3):479-485.
    [5]
    Olas B.Hydrogen sulfide in signaling pathways[J].Clin Chim Acta,2015,439:212-218.
    [6]
    Nagy P.Mechanistic chemical perspective of hydrogen sulfide signaling[J].Methods Enzymol,2015,554:3-29.
    [7]
    Ariyaratnam P,Loubani M,Morice AH.Hydrogen sulphide vasodilates human pulmonary arteries:a possible role in pulmonary hypertension[J].Microvasc Res,2013,90:135-137.
    [8]
    Lefer DJ.A new gaseous signaling molecule emerges:cardioprotective role of hydrogen sulfide[J].Proc Natl Acad Sci U S A,2007,104(46):17907-17908.
    [9]
    Li L,Bhatia M,Zhu YZ,et al.Hydrogen sulfide is a novel mediator of lipopolysaccharide-induced inflammation in the mouse[J].FASEB J,2005,19(9):1196-1198.
    [10]
    Kimura Y,Kimura H.Hydrogen sulfide protects neurons from oxidative stress[J].FASEB J,2004,18(10):1165-1167.
    [11]
    Lee ZW,Zhou J,Chen CS,et al.The slow-releasing hydrogen sulfide donor,GYY4137,exhibits novel anti-cancer effects in vitro and in vivo[J].PLoS One,2011,6(6):e21077.
    [12]
    Kashfi K.Anti-cancer activity of new designer hydrogen sulfide-donating hybrids[J].Antioxid Redox Signal,2014,20(5):831-846.
    [13]
    Beltowski J. Hydrogen sulfide in pharmacology and medicine-An update[J].Pharmacol Rep,2015,67(3):647-658.
    [14]
    Filipovic MR,Miljkovic JL,Nauser T,et al.Chemical characterization of the smallest S-nitrosothiol,HSNO;cellular cross-talk of H2S and S-nitrosothiols[J].J Am Chem Soc,2012,134(29):12016-12027.
    [15]
    Haouzi P,Bell H,Philmon M.Hydrogen sulfide oxidation and the arterial chemoreflex:effect of methemoglobin[J].Respir Physiol Neurobiol,2011,177(3):273-283.
    [16]
    Holwerda KM,Burke SD,Faas MM,et al.Hydrogen sulfide attenuates sFlt1-induced hypertension and renal damage by upregulating vascular endothelial growth factor[J].J Am Soc Nephrol,2014,25(4):717-725.
    [17]
    Hellmich MR,Coletta C,Chao C,et al.The therapeutic potential of cystathionine β-synthetase/hydrogen sulfide inhibition in cancer[J].Antioxid Redox Signal,2015,22(5):424-448.
    [18]
    Ma Z,Bi Q,Wang Y.Hydrogen sulfide accelerates cell cycle progression in oral squamous cell carcinoma cell lines[J].Oral Dis,2015,21(2):156-162.
    [19]
    Pan Y,Ye S,Yuan D,et al.Hydrogen sulfide(H2S)/cystathionine γ-lyase(CSE)pathway contributes to the proliferation of hepatoma cells[J].Mutat Res,2014,763/764:10-18.
    [20]
    Wu DD,Si WR,Wang MJ,et al.Hydrogen sulfide in cancer:friend or foe[J].Nitric Oxide,2015,50:38-45.
    [21]
    Jin HF,Du JB,Tang CS.“Waste gas is not waste”:advance in the research of hydrogen sulfide[J].Acta Physiol Sin(生理学报),2010,62(6):495-504.
    [22]
    Zhao Y,Wang H,Xian M.Cysteine-activated hydrogen sulfide(H2S)donors[J].J Am Chem Soc,2011,133(1):15-17.
    [23]
    Cerda MM,Hammers MD,Earp MS,et al.Applications of synthetic organic tetrasulfides as H2S donors[J].Org Lett,2017,19(9):2314-2317.
    [24]
    Benavides GA,Squadrito GL,Mills RW,et al.Hydrogen sulfide mediates the vasoactivity of garlic[J].Proc Natl Acad Sci U S A,2007,104(46):17977-17982.
    [25]
    Liang D,Wu HX,Wong MV,et al.Diallyl trisulfide is a fast H2S donor,but diallyl disulfide is a slow one:the reaction pathways and intermediates of glutathione with polysulfides[J].Org Lett,2015,17(17):4196-4199.
    [26]
    Li L,Whiteman M,Guan YY,et al.Characterization of a novel,water-soluble hydrogen sulfide-releasing molecule(GYY4137):new insights into the biology of hydrogen sulfide[J].Circulation,2008,117(18):2351-2360.
    [27]
    Whiteman M,Li L,Rose P,et al.The effect of hydrogen sulfide donors on lipopolysaccharide-induced formation of inflammatory mediators in macrophages[J].Antioxid Redox Signal,2010,12(10):1147-1154.
    [28]
    Moore PK,Whiteman M.Chemistry,biochemistry and pharmacology of hydrogen sulfide[M].Handb Exp Pharmacol,2015,230:344-354.
    [29]
    Powell CR,Dillon KM,Matson JB.A review of hydrogen sulfide(H2S)donors:chemistry and potential therapeutic applications[J]. Biochem Pharmacol,2018,149:110-123.
    [30]
    Li L,Rossoni G,Sparatore A,et al.Anti-inflammatory and gastrointestinal effects of a novel diclofenac derivative[J].Free Radical Biol Med,2007,42(5):706-719.
    [31]
    Yin W,Lan L,Huang ZJ,et al.Discovery of a ring-opened derivative of 3-n-butylphthalide bearing NO/H2S-donating moieties as a potential anti-ischemic stroke agent[J].Eur J Med Chem,2016,115:369-380.
    [32]
    Zhao Y,Wang H,Xian M.Cysteine-activated hydrogen sulfide(H2S)donors[J].J Am Chem Soc,2011,133(1):15-17.
    [33]
    Zhao Y,Yang CT,Organ C,et al.Design,synthesis,and cardioprotective effects of N-mercapto-based hydrogen sulfide donors[J].J Med Chem,2015,58(18):7501-7511.
    [34]
    Zheng YQ,Yu BC,Ji KL,et al.Esterase-sensitive prodrugs with tunable release rates and direct generation of hydrogen sulfide[J].Angew Chem Int Ed,2016,55(14):4514-4518.
    [35]
    Zheng YQ, Yu BC, Li Z. An esterase-sensitive prodrug approach for controllable delivery of persulfide species[J].Angew Chem Int Ed,2017,56(39):11749-11753.
    [36]
    Fukushima N,Ieda N,Sasakura K,et al.Synthesis of a photocontrollable hydrogen sulfide donor using ketoprofenate photocages[J].Chem Commun,2014,50(5):587-589.
    [37]
    Fukushima N,Ieda N,Kawaguchi M,et al.Development of photo-controllable hydrogen sulfide donor applicable in live cells[J].Bioorg Med Chem Lett,2015,25(2):175-178.
    [38]
    Venkatesh Y,Das J,Chaudhuri A,et al.Light triggered uncaging of hydrogen sulfide(H2S)with real-time monitoring[J].Chem Commun,2018,54(25):3106-3109.
    [39]
    Luo XJ,Wu JB,Lv T,et al.Synthesis and evaluation of novel O2-derived diazeniumdiolates as photochemical and real-time monitoring nitric oxide delivery agents[J].Org Chem Front,2017,4(12):2445-2449.
    [40]
    Steiger AK,Pardue S,Kevil CG,et al.Self-immolative thiocarbamates provide access to triggered H2S donors and analyte replacement fluorescent probes[J].J Am Chem Soc,2016,138(23):7256-7259.
    [41]
    Chauhan P,Bora P,Ravikumar G,et al.Esterase activated carbonyl sulfide/hydrogen sulfide(H2S)donors[J].Org Lett,2017,19(1):62-65.
    [42]
    Alouane A,Labruere R,Schmidt F,et al.Self-immolative spacers:kinetic aspects,structure-property relationships,and applications[J].Angew Chem Int Ed,2015,54(26):7492-7509.
    [43]
    Steiger AK,Marcatti M,Szabo C,et al. Inhibition of mitochondrial bioenergetics by esterase-triggered COS/H2S donors[J].ACS Chem Biol,2017,12(8):2117-2123.
    [44]
    Zhao Y,Pluth MD.Hydrogen sulfide donors activated by reactive oxygen species[J].Angew Chem Int Ed,2016,55(47):14638-14642.
    [45]
    Li J, Chen PR. Development and application of bond cleavage reactions in bioorthogonal chemistry[J].Nat Chem Biol,2016,12(3):129-137.
    [46]
    Steiger AK,Yang Y,Royzen M,et al.Bio-orthogonal “click-and-release” donation of caged carbonyl sulfide(COS)and hydrogen sulfide(H2S)[J].Chem Commun,2017,53(8):1378-1380.
    [47]
    Zhao Y,Bolton SG,Pluth MD.Light-activated COS/H2S donation from photocaged thiocarbamates[J].Org Lett,2017,19(9):2278-2281.
    [48]
    Sharma AK, Nair M, Chauhan P, et al. Visible-light-triggered uncaging of carbonyl sulfide for hydrogen sulfide(H2S)release[J].Org Lett,2017,19(18):4822-4825.
    [49]
    Hirschmann R,Dewey RS,Schoenewaldt EF,et al.Synthesis of peptides in aqueous medium.VII.Preparation and use of 2,5-thiazolidinediones in peptide synthesis[J].J Org Chem,1971,36(1):49-59.
    [50]
    Powell CR,Foster JC,Okyere B,et al.Therapeutic delivery of H2S via COS:small molecule and polymeric donors with benign byproducts[J].J Am Chem Soc,2016,138(41):13477-13480.
    [51]
    Feng S,Zhao Y,Xian M,et al.Biological thiols-triggered hydrogen sulfide releasing microfibers for tissue engineering applications[J].Acta Biomater,2015,27:205-213.
    [52]
    Wu J,Li Y,He C,et al.Novel H2S releasing nanofibrous coating for in vivo dermal wound regeneration[J].ACS Appl Mater Interfaces,2016,8(41):27474-27481.

Catalog

    Article views (977) PDF downloads (2143) Cited by()

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return