메뉴 건너뛰기




Volumn 80, Issue 3, 2012, Pages 471-478

The Molecular Design of S-Nitrosothiols as Photodynamic Agents for Controlled Nitric Oxide Release

Author keywords

Chemical biology; Drug design; Molecular modeling; Nitric oxide; S nitrosothiol

Indexed keywords

NITRIC OXIDE; S NITROSOTHIOL; TERT BUTYL S NITROSOTHIOL; TERT DODECANE S NITROSOTHIOL; UNCLASSIFIED DRUG;

EID: 84864116058     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2012.01420.x     Document Type: Article
Times cited : (20)

References (42)
  • 1
    • 33749005136 scopus 로고    scopus 로고
    • Nitroxidative, nitrosative, and nitrative stress: kinetic predictions of reactive nitrogen species chemistry under biological conditions
    • Lancaster J.R. Jr (2006) Nitroxidative, nitrosative, and nitrative stress: kinetic predictions of reactive nitrogen species chemistry under biological conditions. Chem Res Toxicol;19:1160-1174.
    • (2006) Chem Res Toxicol , vol.19 , pp. 1160-1174
    • Lancaster Jr, J.R.1
  • 2
    • 1242321336 scopus 로고    scopus 로고
    • The chemistry of nitrosative stress induced by nitric oxide and reactive nitrogen oxide species. Putting perspective on stressful biological situations
    • Ridnour L.A., Thomas D.D., Mancardi D., Espey M.G., Miranda K.M., Paolocci N., Feelisch M., Fukuto J., Wink D.A. (2004) The chemistry of nitrosative stress induced by nitric oxide and reactive nitrogen oxide species. Putting perspective on stressful biological situations. Biol Chem;385:1-10.
    • (2004) Biol Chem , vol.385 , pp. 1-10
    • Ridnour, L.A.1    Thomas, D.D.2    Mancardi, D.3    Espey, M.G.4    Miranda, K.M.5    Paolocci, N.6    Feelisch, M.7    Fukuto, J.8    Wink, D.A.9
  • 3
    • 0031406827 scopus 로고    scopus 로고
    • A mechanistic analysis of nitric oxide-induced cellular toxicity
    • Burney S., Tamir S., Gal A., Tannenbaum S.R. (1997) A mechanistic analysis of nitric oxide-induced cellular toxicity. Nitric Oxide;1:130-144.
    • (1997) Nitric Oxide , vol.1 , pp. 130-144
    • Burney, S.1    Tamir, S.2    Gal, A.3    Tannenbaum, S.R.4
  • 4
    • 0032898838 scopus 로고    scopus 로고
    • Nitric oxide and cell death
    • Murphy M.P. (1999) Nitric oxide and cell death. Biochim Biophys Acta;1411:401-414.
    • (1999) Biochim Biophys Acta , vol.1411 , pp. 401-414
    • Murphy, M.P.1
  • 5
    • 0036901561 scopus 로고    scopus 로고
    • Exogenous ferrous iron is required for the nitric oxide-catalysed destruction of the iron-sulphur centre in adrenodoxin
    • Voevodskaya N.V., Serezhenkov V.A., Cooper C.E., Kubrina L.N., Vanin A.F. (2002) Exogenous ferrous iron is required for the nitric oxide-catalysed destruction of the iron-sulphur centre in adrenodoxin. Biochem J;368:633-639.
    • (2002) Biochem J , vol.368 , pp. 633-639
    • Voevodskaya, N.V.1    Serezhenkov, V.A.2    Cooper, C.E.3    Kubrina, L.N.4    Vanin, A.F.5
  • 6
    • 0030811240 scopus 로고    scopus 로고
    • Effects of diethylamine/nitric oxide on blood perfusion and oxygenation in the R3230Ac mammary carcinoma
    • Shan S.Q., Rosner G.L., Braun R.D., Hahn J., Pearce C., Dewhirst M.W. (1997) Effects of diethylamine/nitric oxide on blood perfusion and oxygenation in the R3230Ac mammary carcinoma. Br J Cancer;76:429-437.
    • (1997) Br J Cancer , vol.76 , pp. 429-437
    • Shan, S.Q.1    Rosner, G.L.2    Braun, R.D.3    Hahn, J.4    Pearce, C.5    Dewhirst, M.W.6
  • 7
    • 79959837612 scopus 로고    scopus 로고
    • Targeted photodynamic therapy - a promising strategy of tumor treatment
    • Bugaj A.M. (2011) Targeted photodynamic therapy - a promising strategy of tumor treatment. Photochem Photobiol Sci;10:1097-1109.
    • (2011) Photochem Photobiol Sci , vol.10 , pp. 1097-1109
    • Bugaj, A.M.1
  • 8
    • 0028411281 scopus 로고
    • Visible light photochemical release of nitric oxide from S-nitrosoglutathione: potential photochemotherapeutic applications
    • Sexton D.J., Muruganandam A., McKenney D.J., Mutus B. (1994) Visible light photochemical release of nitric oxide from S-nitrosoglutathione: potential photochemotherapeutic applications. Photochem Photobiol;59:463-467.
    • (1994) Photochem Photobiol , vol.59 , pp. 463-467
    • Sexton, D.J.1    Muruganandam, A.2    McKenney, D.J.3    Mutus, B.4
  • 9
    • 0032011535 scopus 로고    scopus 로고
    • Control of NO concentration in solutions of nitrosothiol compounds by light
    • Zhelyaskov V.R., Gee K.R., Godwin D.W. (1998) Control of NO concentration in solutions of nitrosothiol compounds by light. Photochem Photobiol;67:282-288.
    • (1998) Photochem Photobiol , vol.67 , pp. 282-288
    • Zhelyaskov, V.R.1    Gee, K.R.2    Godwin, D.W.3
  • 10
    • 0029648407 scopus 로고
    • Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane possible use for site-directed nitric-oxide production
    • Singh R.J., Hogg N., Joseph J., Kalyanaraman B. (1995) Photosensitized decomposition of S-nitrosothiols and 2-methyl-2-nitrosopropane possible use for site-directed nitric-oxide production. FEBS Lett;360:47-51.
    • (1995) FEBS Lett , vol.360 , pp. 47-51
    • Singh, R.J.1    Hogg, N.2    Joseph, J.3    Kalyanaraman, B.4
  • 14
    • 43849090222 scopus 로고    scopus 로고
    • Thiyl radicals react with nitric oxide to form S-nitrosothiols with rate constants near the diffusion-controlled limit
    • Madej E., Folkes L.K., Wardman P., Czapski G., Goldstein S. (2008) Thiyl radicals react with nitric oxide to form S-nitrosothiols with rate constants near the diffusion-controlled limit. Free Radic Biol Med;44:2013-2018.
    • (2008) Free Radic Biol Med , vol.44 , pp. 2013-2018
    • Madej, E.1    Folkes, L.K.2    Wardman, P.3    Czapski, G.4    Goldstein, S.5
  • 15
    • 0036176869 scopus 로고    scopus 로고
    • Potential therapeutic uses for S-nitrosothiols
    • Richardson G., Benjamin N. (2002) Potential therapeutic uses for S-nitrosothiols. Clin Sci (Lond);102:99-105.
    • (2002) Clin Sci (Lond) , vol.102 , pp. 99-105
    • Richardson, G.1    Benjamin, N.2
  • 17
    • 0029780524 scopus 로고    scopus 로고
    • Mechanism of nitric oxide release from S-nitrosothiols
    • Singh R.J., Hogg N., Joseph J., Kalyanaraman B. (1996) Mechanism of nitric oxide release from S-nitrosothiols. J Biol Chem;271:18596-18603.
    • (1996) J Biol Chem , vol.271 , pp. 18596-18603
    • Singh, R.J.1    Hogg, N.2    Joseph, J.3    Kalyanaraman, B.4
  • 18
    • 0034524577 scopus 로고    scopus 로고
    • A novel family of S-nitrosothiols: chemical synthesis and biological actions
    • Al-Sa'doni H.H., Khan I.Y., Poston L., Fisher I., Ferro A. (2000) A novel family of S-nitrosothiols: chemical synthesis and biological actions. Nitric Oxide;4:550-560.
    • (2000) Nitric Oxide , vol.4 , pp. 550-560
    • Al-Sa'doni, H.H.1    Khan, I.Y.2    Poston, L.3    Fisher, I.4    Ferro, A.5
  • 19
    • 0037127043 scopus 로고    scopus 로고
    • A kinetic study of S-nitrosothiol decomposition
    • Grossi L., Montevecchi P.C. (2002) A kinetic study of S-nitrosothiol decomposition. Chemistry;8:380-387.
    • (2002) Chemistry , vol.8 , pp. 380-387
    • Grossi, L.1    Montevecchi, P.C.2
  • 20
    • 0033592814 scopus 로고    scopus 로고
    • Nitric oxide release from S-nitrosoglutathione (GSNO)
    • Noble D.R., Swift H.R., Williams D.L.H. (1999) Nitric oxide release from S-nitrosoglutathione (GSNO). Chem Commun;22:2317-2318.
    • (1999) Chem Commun , vol.22 , pp. 2317-2318
    • Noble, D.R.1    Swift, H.R.2    Williams, D.L.H.3
  • 21
    • 9744286818 scopus 로고
    • New thionitrites - synthesis, stability, and nitric-oxide generation
    • Roy B., Dhardemare A.D., Fontecave M. (1994) New thionitrites - synthesis, stability, and nitric-oxide generation. J Org Chem;59:7019-7026.
    • (1994) J Org Chem , vol.59 , pp. 7019-7026
    • Roy, B.1    Dhardemare, A.D.2    Fontecave, M.3
  • 22
    • 0035555992 scopus 로고    scopus 로고
    • S-nitrosothiols: materials, reactivity and mechanisms
    • Szacilowski K., Stasicka Z. (2001) S-nitrosothiols: materials, reactivity and mechanisms. Prog React Kinet;26:1-58.
    • (2001) Prog React Kinet , vol.26 , pp. 1-58
    • Szacilowski, K.1    Stasicka, Z.2
  • 24
    • 0036591864 scopus 로고    scopus 로고
    • Mixing artifacts from the bolus addition of nitric oxide to oxymyoglobin: implications for S-nitrosothiol formation
    • Zhang Y., Hogg N. (2002) Mixing artifacts from the bolus addition of nitric oxide to oxymyoglobin: implications for S-nitrosothiol formation. Free Radic Biol Med;32:1212-1219.
    • (2002) Free Radic Biol Med , vol.32 , pp. 1212-1219
    • Zhang, Y.1    Hogg, N.2
  • 26
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays
    • Mosmann T. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods;65:55-63.
    • (1983) J Immunol Methods , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 27
    • 4544379340 scopus 로고    scopus 로고
    • S-nitrosothiols as nitric oxide-donors: chemistry, biology and possible future therapeutic applications
    • Al-Sa'doni H.H., Ferro A. (2004) S-nitrosothiols as nitric oxide-donors: chemistry, biology and possible future therapeutic applications. Curr Med Chem;11:2679-2690.
    • (2004) Curr Med Chem , vol.11 , pp. 2679-2690
    • Al-Sa'doni, H.H.1    Ferro, A.2
  • 28
    • 0042863397 scopus 로고    scopus 로고
    • Thresholds of nitric oxide-mediated toxicity in human lymphoblastoid cells
    • Wang C., Trudel L.J., Wogan G.N., Deen W.M. (2003) Thresholds of nitric oxide-mediated toxicity in human lymphoblastoid cells. Chem Res Toxicol;16:1004-1013.
    • (2003) Chem Res Toxicol , vol.16 , pp. 1004-1013
    • Wang, C.1    Trudel, L.J.2    Wogan, G.N.3    Deen, W.M.4
  • 29
    • 0034717317 scopus 로고    scopus 로고
    • Kinetic characterization of the nitric oxide toxicity for PC12 cells: effect of half-life time of NO release
    • Yamamoto T., Yuyama K., Nakamura K., Kato T., Yamamoto H. (2000) Kinetic characterization of the nitric oxide toxicity for PC12 cells: effect of half-life time of NO release. Eur J Pharmacol;397:25-33.
    • (2000) Eur J Pharmacol , vol.397 , pp. 25-33
    • Yamamoto, T.1    Yuyama, K.2    Nakamura, K.3    Kato, T.4    Yamamoto, H.5
  • 30
    • 0036254648 scopus 로고    scopus 로고
    • Reactive sulfur species: an emerging concept in oxidative stress
    • Giles G.I., Jacob C. (2002) Reactive sulfur species: an emerging concept in oxidative stress. Biol Chem;383:375-388.
    • (2002) Biol Chem , vol.383 , pp. 375-388
    • Giles, G.I.1    Jacob, C.2
  • 31
    • 0036606781 scopus 로고    scopus 로고
    • Reactive sulphur species: an in vitro investigation of the oxidation properties of disulphide S-oxides
    • Giles G.I., Tasker K.M., Collins C., Giles N.M., O'Rourke E., Jacob C. (2002) Reactive sulphur species: an in vitro investigation of the oxidation properties of disulphide S-oxides. Biochem J;364:579-585.
    • (2002) Biochem J , vol.364 , pp. 579-585
    • Giles, G.I.1    Tasker, K.M.2    Collins, C.3    Giles, N.M.4    O'Rourke, E.5    Jacob, C.6
  • 32
    • 0035890243 scopus 로고    scopus 로고
    • Hypothesis: the role of reactive sulfur species in oxidative stress
    • Giles G.I., Tasker K.M., Jacob C. (2001) Hypothesis: the role of reactive sulfur species in oxidative stress. Free Radic Biol Med;31:1279-1283.
    • (2001) Free Radic Biol Med , vol.31 , pp. 1279-1283
    • Giles, G.I.1    Tasker, K.M.2    Jacob, C.3
  • 33
    • 0036011097 scopus 로고    scopus 로고
    • Oxidation of biological thiols by highly reactive disulfide-S-oxides
    • Giles G.I., Tasker K.M., Jacob C. (2002) Oxidation of biological thiols by highly reactive disulfide-S-oxides. Gen Physiol Biophys;21:65-72.
    • (2002) Gen Physiol Biophys , vol.21 , pp. 65-72
    • Giles, G.I.1    Tasker, K.M.2    Jacob, C.3
  • 34
    • 10644269917 scopus 로고    scopus 로고
    • Reactive sulphur species in oxidative signal transduction
    • Jacob C., Lancaster J.R., Giles G.I. (2004) Reactive sulphur species in oxidative signal transduction. Biochem Soc Trans;32:1015-1017.
    • (2004) Biochem Soc Trans , vol.32 , pp. 1015-1017
    • Jacob, C.1    Lancaster, J.R.2    Giles, G.I.3
  • 36
    • 71749096160 scopus 로고    scopus 로고
    • Chloroquine and its analogs: a new promise of an old drug for effective and safe cancer therapies
    • Solomon V.R., Lee H. (2009) Chloroquine and its analogs: a new promise of an old drug for effective and safe cancer therapies. Eur J Pharmacol;625:220-233.
    • (2009) Eur J Pharmacol , vol.625 , pp. 220-233
    • Solomon, V.R.1    Lee, H.2
  • 37
    • 0018593843 scopus 로고
    • The binding of drugs to different polar lipids in vitro
    • 38.
    • Lullmann H., Wehlig M. (1979) The binding of drugs to different polar lipids in vitro. Biochem Pharm;28:3409-3415.38.
    • (1979) Biochem Pharm , vol.28 , pp. 3409-3415
    • Lullmann, H.1    Wehlig, M.2
  • 38
    • 0033179183 scopus 로고    scopus 로고
    • Recognizing molecules with drug-like properties
    • Walters W.P., Ajay, Murcko M.A. (1999) Recognizing molecules with drug-like properties. Curr Opin Chem Biol;3:384-387.
    • (1999) Curr Opin Chem Biol , vol.3 , pp. 384-387
    • Walters, W.P.1    Ajay2    Murcko, M.A.3
  • 39
    • 0343986372 scopus 로고    scopus 로고
    • Cellular antioxidant and pro-oxidant actions of nitric oxide
    • Joshi M.S., Ponthier J.L., Lancaster J.R. Jr (1999) Cellular antioxidant and pro-oxidant actions of nitric oxide. Free Radic Biol Med;27:1357-1366.
    • (1999) Free Radic Biol Med , vol.27 , pp. 1357-1366
    • Joshi, M.S.1    Ponthier, J.L.2    Lancaster Jr, J.R.3
  • 40
    • 84864149521 scopus 로고    scopus 로고
    • Nitrogen monoxide (nitric oxide): bioinorganic chemistry
    • In: King R.B., editor., 2nd edn. Chichester, UK: Wiley; p. -.
    • Lancaster J.R. Jr, Giles G.I. (2005) Nitrogen monoxide (nitric oxide): bioinorganic chemistry. In: King R.B., editor. Encyclopedia of Inorganic Chemistry, 2nd edn. Chichester, UK: Wiley; p. 1-21.
    • (2005) Encyclopedia of Inorganic Chemistry , pp. 1-21
    • Lancaster Jr, J.R.1    Giles, G.I.2
  • 41
    • 63849246674 scopus 로고    scopus 로고
    • Discovery of the nitric oxide signaling pathway and targets for drug development
    • Bryan N.S., Bian K., Murad F. (2009) Discovery of the nitric oxide signaling pathway and targets for drug development. Front Biosci;14:1-18.
    • (2009) Front Biosci , vol.14 , pp. 1-18
    • Bryan, N.S.1    Bian, K.2    Murad, F.3
  • 42
    • 33751519059 scopus 로고    scopus 로고
    • Nitric oxide and the regulation of apoptosis in tumour cells
    • Tarr J.M., Eggleton P., Winyard P.G. (2006) Nitric oxide and the regulation of apoptosis in tumour cells. Curr Pharm Des;12:4445-4468.
    • (2006) Curr Pharm Des , vol.12 , pp. 4445-4468
    • Tarr, J.M.1    Eggleton, P.2    Winyard, P.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.