메뉴 건너뛰기




Volumn 7, Issue 7, 2015, Pages 857-871

Searching phase II enzymes inducers, from Michael acceptor-[1,2]dithiolethione hybrids, as cancer chemopreventive agents

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DITHIOLE 3 THIONE DERIVATIVE; 4' BROMOFLAVONE; 5 [4 (2 PHENYLETHANOYLOXY)PHENYL] 3H [1,2]DITHIOLE 3 THIONE; 5 [4 (3 PHENYL 2 PROPENOYLOXY)PHENYL] 3H [1,2]DITHIOLE 3 THIONE; 5 [4 [4 (3 OXO 3 PHENYL 5 [4 [4 (3 OXO 3 PHENYL 1 PROPENYL)]BENZOYLOXY]PHENYL] 3H [1,2]DITHIOLE 3 THIONE; 5 [4 [4 [3 (2 HYDROXYPHENYL) 3 OXO 1 PROPENYL)] BENZOYLOXY]PHENYL] 3H [1,2]DITHIOLE 3 THIONE; ANTINEOPLASTIC AGENT; CYTOTOXIC AGENT; ENZYME INDUCING AGENT; GLUTATHIONE S TRANSFERASE INDUCER; GLUTATHIONE TRANSFERASE; QUINONE REDUCTASE INDUCER; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE (PHOSPHATE) DEHYDROGENASE (QUINONE); TERT BUTYLHYDROQUINONE; UNCLASSIFIED DRUG; 5-(4-(3-PHENYL-2-PROPENOYLOXY)PHENYL)-3H-(1,2)DITHIOLE-3-THIONE; CINNAMIC ACID DERIVATIVE; SINGLE HETEROCYCLIC RINGS;

EID: 84931092534     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.15.32     Document Type: Article
Times cited : (13)

References (39)
  • 1
    • 33645993864 scopus 로고    scopus 로고
    • Quinone reductase induction as a biomarker for cancer chemoprevention
    • Cuendet M, Oteham CP, Moon RC, Pezzuto JM. Quinone reductase induction as a biomarker for cancer chemoprevention. J. Nat. Prod. 69(3), 460-463 (2006).
    • (2006) J. Nat. Prod. , vol.69 , Issue.3 , pp. 460-463
    • Cuendet, M.1    Oteham, C.P.2    Moon, R.C.3    Pezzuto, J.M.4
  • 2
    • 9744222928 scopus 로고    scopus 로고
    • Potential synergy of phytochemicals in cancer prevention: Mechanism of action
    • Liu RH. Potential synergy of phytochemicals in cancer prevention: mechanism of action. J. Nutr. 134(Suppl. 12), s3479-s3485 (2004).
    • (2004) J. Nutr. , vol.134 , pp. s3479-s3485
    • Liu, R.H.1
  • 3
    • 0030825875 scopus 로고    scopus 로고
    • Quercetin and myricetin protect against hydrogen peroxide-induced DNA damage (strand breaks and oxidized pyrimidines) in human lymphocytes
    • Duthie SJ, Collins AR, Duthie GG, Dodson VL. Quercetin and myricetin protect against hydrogen peroxide-induced DNA damage (strand breaks and oxidized pyrimidines) in human lymphocytes. Mutat. Res. 393(3), 223-231 (1997).
    • (1997) Mutat. Res. , vol.393 , Issue.3 , pp. 223-231
    • Duthie, S.J.1    Collins, A.R.2    Duthie, G.G.3    Dodson, V.L.4
  • 4
    • 0344915418 scopus 로고
    • Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis
    • Talalay P, De Long MJ, Prochaska HJ. Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis. Proc. Natl Acad. Sci. USA 85(21), 8261-8265 (1988).
    • (1988) Proc. Natl Acad. Sci. USA , vol.85 , Issue.21 , pp. 8261-8265
    • Talalay, P.1    De Long, M.J.2    Prochaska, H.J.3
  • 5
    • 2942568014 scopus 로고    scopus 로고
    • Dietary chemopreventive compounds and ARE/EpRE signaling
    • Chen C, Kong AN. Dietary chemopreventive compounds and ARE/EpRE signaling. Free Radic. Biol. Med. 36(12), 1505-1516 (2004).
    • (2004) Free Radic. Biol. Med. , vol.36 , Issue.12 , pp. 1505-1516
    • Chen, C.1    Kong, A.N.2
  • 6
    • 9644272830 scopus 로고    scopus 로고
    • Protection against electrophile and oxidative stress by induction of phase 2 genes: The quest for the elusive sensor that responds to inducers
    • Hotzclaw WD, Dinkova-Kostova AT, Talalay P. Protection against electrophile and oxidative stress by induction of phase 2 genes: the quest for the elusive sensor that responds to inducers. Adv. Enzyme Regul. 44, 335-367 (2004).
    • (2004) Adv. Enzyme Regul. , vol.44 , pp. 335-367
    • Hotzclaw, W.D.1    Dinkova-Kostova, A.T.2    Talalay, P.3
  • 7
    • 77952600786 scopus 로고    scopus 로고
    • Anti-inflammatory and chemopreventive effects of triterpene cinnamates and acetates from shea fat
    • Akihisa T, Kojima N, Kikuchi T et al. Anti-inflammatory and chemopreventive effects of triterpene cinnamates and acetates from shea fat. J. Oleo Sci. 59(6), 273-280 (2010).
    • (2010) J. Oleo Sci. , vol.59 , Issue.6 , pp. 273-280
    • Akihisa, T.1    Kojima, N.2    Kikuchi, T.3
  • 8
    • 23344450788 scopus 로고    scopus 로고
    • Induction of phase I, II and III drug metabolism/transport by xenobiotics
    • Xu C, Li CY, Kong AN. Induction of phase I, II and III drug metabolism/transport by xenobiotics. Arch. Pharm. Res. 28(3), 249-268 (2005).
    • (2005) Arch. Pharm. Res. , vol.28 , Issue.3 , pp. 249-268
    • Xu, C.1    Li, C.Y.2    Kong, A.N.3
  • 9
    • 46649090917 scopus 로고    scopus 로고
    • Cinnamoylbased Nrf2-activators targeting human skin cell photooxidative stress
    • Wondrak GT, Cabello CM, Villeneuve NF et al. Cinnamoylbased Nrf2-activators targeting human skin cell photooxidative stress. Free Rad. Biol. Med. 45(4), 385-395 (2008).
    • (2008) Free Rad. Biol. Med. , vol.45 , Issue.4 , pp. 385-395
    • Wondrak, G.T.1    Cabello, C.M.2    Villeneuve, N.F.3
  • 10
    • 34547882115 scopus 로고    scopus 로고
    • Resveratrol: A review of preclinical studies for human cancer prevention
    • Athar M, Back JH, Tang X et al. Resveratrol: a review of preclinical studies for human cancer prevention. Toxicol. Appl. Pharmacol. 224(3), 274-283 (2007).
    • (2007) Toxicol. Appl. Pharmacol. , vol.224 , Issue.3 , pp. 274-283
    • Athar, M.1    Back, J.H.2    Tang, X.3
  • 11
    • 0031417008 scopus 로고    scopus 로고
    • Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids, diosmin and hesperidin
    • Tanaka T, Makita H, Kawabata K et al. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids, diosmin and hesperidin. Carcinogenesis 18(5), 957-965 (1997).
    • (1997) Carcinogenesis , vol.18 , Issue.5 , pp. 957-965
    • Tanaka, T.1    Makita, H.2    Kawabata, K.3
  • 12
    • 77955336343 scopus 로고    scopus 로고
    • Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers
    • Cabrera M, Lavaggi ML, Croce F et al. Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers. Bioorg. Med. Chem. 18(14), 5391-5399 (2010).
    • (2010) Bioorg. Med. Chem. , vol.18 , Issue.14 , pp. 5391-5399
    • Cabrera, M.1    Lavaggi, M.L.2    Croce, F.3
  • 14
    • 0036716819 scopus 로고    scopus 로고
    • Identification of potential prostate cancer preventive agents through induction of quinone reductase in vitro
    • Brooks JD, Goldberg MF, Nelson LA, Wu D, Nelson WG. Identification of potential prostate cancer preventive agents through induction of quinone reductase in vitro. Cancer Epidemiol. Biomarkers Prev. 11(9), 868-875 (2002).
    • (2002) Cancer Epidemiol. Biomarkers Prev. , vol.11 , Issue.9 , pp. 868-875
    • Brooks, J.D.1    Goldberg, M.F.2    Nelson, L.A.3    Wu, D.4    Nelson, W.G.5
  • 15
    • 56249128623 scopus 로고    scopus 로고
    • Dithiolethiones for cancer chemoprevention: Where do we stand
    • Zhang Y, Munday R. Dithiolethiones for cancer chemoprevention: where do we stand Mol. Cancer. Ther. 7(11), 3470-3479 (2008).
    • (2008) Mol. Cancer. Ther. , vol.7 , Issue.11 , pp. 3470-3479
    • Zhang, Y.1    Munday, R.2
  • 16
    • 84873410143 scopus 로고    scopus 로고
    • Biology and therapeutic potential of hydrogen sulfide and hydrogen sulfide-releasing chimeras
    • Kashfi K, Olson KR. Biology and therapeutic potential of hydrogen sulfide and hydrogen sulfide-releasing chimeras. Biochem. Pharmacol. 85(5), 689-703 (2013).
    • (2013) Biochem. Pharmacol. , vol.85 , Issue.5 , pp. 689-703
    • Kashfi, K.1    Olson, K.R.2
  • 17
    • 34548380363 scopus 로고    scopus 로고
    • Keap1 eye on the target: Chemoprevention of liver cancer
    • Yates MS, Kensler TW. Keap1 eye on the target: chemoprevention of liver cancer. Acta Pharmacol. Sin. 28(9), 1331-1342 (2007).
    • (2007) Acta Pharmacol. Sin. , vol.28 , Issue.9 , pp. 1331-1342
    • Yates, M.S.1    Kensler, T.W.2
  • 18
    • 77953789214 scopus 로고    scopus 로고
    • Synthesis, biological evaluation, and structureactivity relationships of dithiolethiones as inducers of cytoprotective phase 2 enzymes
    • Munday R, Zhang Y, Paonessa JD, Munday CM, Wilkins AL, Babu J. Synthesis, biological evaluation, and structureactivity relationships of dithiolethiones as inducers of cytoprotective phase 2 enzymes. J. Med. Chem. 53(12), 4761-4767 (2010).
    • (2010) J. Med. Chem. , vol.53 , Issue.12 , pp. 4761-4767
    • Munday, R.1    Zhang, Y.2    Paonessa, J.D.3    Munday, C.M.4    Wilkins, A.L.5    Babu, J.6
  • 19
    • 84858182910 scopus 로고    scopus 로고
    • NOSH-Aspirin: A novel nitric oxide-hydrogen sulfide-releasing hybrid: A new class of anti-inflammatory pharmaceuticals
    • Kodela R, Chattopadhyay M, Kashfi K. NOSH-Aspirin: a novel nitric oxide-hydrogen sulfide-releasing hybrid: a new class of anti-inflammatory pharmaceuticals. ACS Med. Chem. Lett. 3(3), 257-262 (2012).
    • (2012) ACS Med. Chem. Lett. , vol.3 , Issue.3 , pp. 257-262
    • Kodela, R.1    Chattopadhyay, M.2    Kashfi, K.3
  • 20
    • 68949092109 scopus 로고    scopus 로고
    • Hydrogen peroxide is a second messenger in phase 2 enzyme induction by cancer chemopreventive dithiolethiones
    • Holland R, Navamal M, Velayutham M, Zweier JL, Kensler TW, Fishbein JC. Hydrogen peroxide is a second messenger in phase 2 enzyme induction by cancer chemopreventive dithiolethiones. Chem. Res. Toxicol. 22(8), 1427-1434 (2009).
    • (2009) Chem. Res. Toxicol. , vol.22 , Issue.8 , pp. 1427-1434
    • Holland, R.1    Navamal, M.2    Velayutham, M.3    Zweier, J.L.4    Kensler, T.W.5    Fishbein, J.C.6
  • 21
    • 62349124312 scopus 로고    scopus 로고
    • Chemical genomics of cancer chemopreventive dithiolethiones
    • Tran QT, Xu L, Phan V et al. Chemical genomics of cancer chemopreventive dithiolethiones. Carcinogenesis 30(3), 480-486 (2009).
    • (2009) Carcinogenesis , vol.30 , Issue.3 , pp. 480-486
    • Tran, Q.T.1    Xu, L.2    Phan, V.3
  • 22
    • 0023777834 scopus 로고
    • Regulatory mechanisms of monofunctional and bifunctional anticarcinogenic enzyme inducers in murine liver
    • Prochaska HJ, Talalay P. Regulatory mechanisms of monofunctional and bifunctional anticarcinogenic enzyme inducers in murine liver. Cancer Res. 48(17), 4776-4782 (1988).
    • (1988) Cancer Res. , vol.48 , Issue.17 , pp. 4776-4782
    • Prochaska, H.J.1    Talalay, P.2
  • 23
    • 84858281328 scopus 로고    scopus 로고
    • Chemopreventive effects of free and bound phenolics associated to steep waters (nejayote) obtained after nixtamalization of different maize types
    • Rojas-Garciá C, Garciá-Lara S, Serna-Saldivar SO, Gutiérrez-Uribe JA. Chemopreventive effects of free and bound phenolics associated to steep waters (nejayote) obtained after nixtamalization of different maize types. Plant Foods Hum. Nutr. 67(1), 94-99 (2012).
    • (2012) Plant Foods Hum. Nutr. , vol.67 , Issue.1 , pp. 94-99
    • Rojas-Garciá, C.1    Garciá-Lara, S.2    Serna-Saldivar, S.O.3    Gutiérrez-Uribe, J.A.4
  • 24
    • 34047185373 scopus 로고    scopus 로고
    • Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure-activity relationships
    • Cabrera M, Simoens M, Falchi G et al. Synthetic chalcones, flavanones, and flavones as antitumoral agents: biological evaluation and structure-activity relationships. Bioorg. Med. Chem. 15(10), 3356-3367 (2007).
    • (2007) Bioorg. Med. Chem. , vol.15 , Issue.10 , pp. 3356-3367
    • Cabrera, M.1    Simoens, M.2    Falchi, G.3
  • 25
    • 84922656056 scopus 로고    scopus 로고
    • DMAP-promoted cascade C-S/C-N bonds formation approach to 1, 3-thiazolidin-4-ones via annulation of-ketothiamides with-halocarboxylic acids at room temperature
    • Verma GK, Shukla G, Nagaraju A, Srivastava A, Singh MS. DMAP-promoted cascade C-S/C-N bonds formation approach to 1, 3-thiazolidin-4-ones via annulation of-ketothiamides with-halocarboxylic acids at room temperature. Tetrahedron 70(39), 6980-6984 (2014).
    • (2014) Tetrahedron , vol.70 , Issue.39 , pp. 6980-6984
    • Verma, G.K.1    Shukla, G.2    Nagaraju, A.3    Srivastava, A.4    Singh, M.S.5
  • 27
    • 84898792975 scopus 로고    scopus 로고
    • A serendipitous one-step conversion of 3H-1, 2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1, 2-dithiole: An experimental and theoretical study
    • Couto M, Cabrera M, Echeverriá GA, Piro OE, González M, Cerecetto H. A serendipitous one-step conversion of 3H-1, 2-dithiole-3-thione to (E)-3-[1-(alkylthio)alkylidene]-3H-1, 2-dithiole: an experimental and theoretical study. Mol. Divers. 18(2), 285-294 (2014).
    • (2014) Mol. Divers. , vol.18 , Issue.2 , pp. 285-294
    • Couto, M.1    Cabrera, M.2    Echeverriá, G.A.3    Piro, O.E.4    González, M.5    Cerecetto, H.6
  • 28
    • 84898771096 scopus 로고
    • Reactivity of 3-acyl methylthio-5-aryl 1, 2-dithiolium bromides
    • Caillaud G, Mollier Y. Reactivity of 3-acyl methylthio-5-aryl 1, 2-dithiolium bromides. Bull. Soc. Chim. Fr. 331-332 (1971).
    • (1971) Bull. Soc. Chim. Fr. , pp. 331-332
    • Caillaud, G.1    Mollier, Y.2
  • 29
    • 84898801097 scopus 로고
    • No 25.-Composés sulfurés hétérocycliques. LVII. Préparation de bromures d'acylméthylthio-3 dithiole-1, 2 ylium
    • Caillaud G, Mollier Y. No 25.-Composés sulfurés hétérocycliques. LVII. Préparation de bromures d'acylméthylthio-3 dithiole-1, 2 ylium. Bull. Soc. Chim. Fr. 147-151 (1972).
    • (1972) Bull. Soc. Chim. Fr. , pp. 147-151
    • Caillaud, G.1    Mollier, Y.2
  • 30
    • 6444236764 scopus 로고
    • No 26.-Composés sulfurés hétérocycliques. LVIII. Reáctivité des bromures d'acylméthylthio-3 dithiole-1, 2 ylium
    • Caillaud G, Mollier Y. No 26.-Composés sulfurés hétérocycliques. LVIII. Reáctivité des bromures d'acylméthylthio-3 dithiole-1, 2 ylium. Bull. Soc. Chim. Fr. 151-161 (1972).
    • (1972) Bull. Soc. Chim. Fr. , pp. 151-161
    • Caillaud, G.1    Mollier, Y.2
  • 31
    • 0022739951 scopus 로고
    • 1, 2-Dithiol-3-thione analogs: Effects on NAD(P)H:quinone reductase and glutathione levels in murine hepatoma cells
    • De Long MJ, Dolan P, Santamaria AB, Bueding E. 1, 2-Dithiol-3-thione analogs: effects on NAD(P)H:quinone reductase and glutathione levels in murine hepatoma cells. Carcinogenesis 7(6), 977-980 (1986).
    • (1986) Carcinogenesis , vol.7 , Issue.6 , pp. 977-980
    • De Long, M.J.1    Dolan, P.2    Santamaria, A.B.3    Bueding, E.4
  • 32
    • 0035853101 scopus 로고    scopus 로고
    • Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups
    • Dinkova-Kostova AT, Massiah MA, Bozak RE, Hicks RJ, Talalay P. Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups. Proc. Natl Acad. Sci. USA 98(6), 3404-3409 (2001).
    • (2001) Proc. Natl Acad. Sci. USA , vol.98 , Issue.6 , pp. 3404-3409
    • Dinkova-Kostova, A.T.1    Massiah, M.A.2    Bozak, R.E.3    Hicks, R.J.4    Talalay, P.5
  • 34
    • 0004127271 scopus 로고    scopus 로고
    • Wavefunction Inc Wavefunction Inc. Irvine, CA, USA
    • Wavefunction Inc. A PC Spartan Pro User's Guide, 1.0. Wavefunction Inc. Irvine, CA, USA (1999).
    • (1999) A PC Spartan Pro User's Guide, 1.0
  • 37
    • 33846104269 scopus 로고    scopus 로고
    • Synthesis of 5-(alkylthio or arylthio)-3H-1, 2-dithiol-3-one derivatives
    • Fracaroli AM, Kreiker J, de Rossi RH, Granados AM. Synthesis of 5-(alkylthio or arylthio)-3H-1, 2-dithiol-3-one derivatives. Arkivoc 4, 279-2844 (2007).
    • (2007) Arkivoc , vol.4 , pp. 279-2844
    • Fracaroli, A.M.1    Kreiker, J.2    De Rossi, R.H.3    Granados, A.M.4
  • 39
    • 33750944756 scopus 로고    scopus 로고
    • Structural requirement of chalcones for the inhibitory activity of interleukin-5
    • Yang HM, Shin HR, Cho SH et al. Structural requirement of chalcones for the inhibitory activity of interleukin-5. Bioorg. Med. Chem. 15(1), 104-111 (2007).
    • (2007) Bioorg. Med. Chem. , vol.15 , Issue.1 , pp. 104-111
    • Yang, H.M.1    Shin, H.R.2    Cho, S.H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.