메뉴 건너뛰기




Volumn 51, Issue 16, 2008, Pages 5118-5120

Reductive heme-dependent activation of the N-oxide prodrug AQ4N by nitric oxide synthase

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BIS[[2 (DIMETHYLAMINO N OXIDE)ETHYL]AMINO] 5,8 DIHYDROXYANTHRAQUINONE; HEME; IRON; NITRIC OXIDE SYNTHASE; PRODRUG;

EID: 50249160554     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800496s     Document Type: Article
Times cited : (35)

References (29)
  • 1
    • 0034176782 scopus 로고    scopus 로고
    • Exploiting the hypoxic cancer cell: Mechanisms and therapeutic strategies
    • (a) Brown, M. J. Exploiting the hypoxic cancer cell: mechanisms and therapeutic strategies. Mol. Med Today 2000, 6, 157-162.
    • (2000) Mol. Med Today , vol.6 , pp. 157-162
    • Brown, M.J.1
  • 2
    • 33846415800 scopus 로고    scopus 로고
    • Hypoxia, drug therapy and toxicity
    • (b) Lee, K.; Roth, R. A.; LaPres, J. J. Hypoxia, drug therapy and toxicity. Pharmacol. Ther. 2007, 113, 229-246.
    • (2007) Pharmacol. Ther , vol.113 , pp. 229-246
    • Lee, K.1    Roth, R.A.2    LaPres, J.J.3
  • 3
    • 0033405294 scopus 로고    scopus 로고
    • The hypoxic cell: A target for selective cancer therapy. Eighteenth Bruce F. Cain Memorial Award lecture
    • Brown, M. J. The hypoxic cell: a target for selective cancer therapy. Eighteenth Bruce F. Cain Memorial Award lecture. Cancer Res. 1999, 59, 5863-5870.
    • (1999) Cancer Res , vol.59 , pp. 5863-5870
    • Brown, M.J.1
  • 4
    • 0029360580 scopus 로고    scopus 로고
    • Tomasz, M. Mitomycin C: small, fast and deadly (but very selective). Chem. Biol. 1995, 2, 575-579.
    • Tomasz, M. Mitomycin C: small, fast and deadly (but very selective). Chem. Biol. 1995, 2, 575-579.
  • 5
    • 0344629821 scopus 로고    scopus 로고
    • NLCQ-1 (NSC 709257): Exploiting hypoxia with a weak DNA-intercalating bioreductive drug
    • Papadopoulou, M. V.; Bloomer, W. D. NLCQ-1 (NSC 709257): exploiting hypoxia with a weak DNA-intercalating bioreductive drug. Clin. Cancer Res. 2003, 9, 5714-5720.
    • (2003) Clin. Cancer Res , vol.9 , pp. 5714-5720
    • Papadopoulou, M.V.1    Bloomer, W.D.2
  • 6
    • 21544441743 scopus 로고    scopus 로고
    • 1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[[1-(4-nitrophenyl)ethoxy-]carbonyl] hydrazine: An anticancer agent targeting hypoxic cells
    • Seow, H. A.; Penketh, P. G.; Shyam, K.; Rockwell, S.; Sartorelli, A. C. 1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[[1-(4-nitrophenyl)ethoxy-]carbonyl] hydrazine: an anticancer agent targeting hypoxic cells. Proc. Nat. Acad. Sci. U.S.A. 2005, 102, 9282-9287.
    • (2005) Proc. Nat. Acad. Sci. U.S.A , vol.102 , pp. 9282-9287
    • Seow, H.A.1    Penketh, P.G.2    Shyam, K.3    Rockwell, S.4    Sartorelli, A.C.5
  • 7
    • 34247517825 scopus 로고    scopus 로고
    • Selective tumor targeting by the hypoxia-activated prodrug AQ4N blocks tumor growth and metastasis in preclinical models of pancreatic cancer
    • (a) Lalani, A. S.; Alters, S. E.; Wong, A.; Albertella, M. R.; Cleland, J. L.; Henner, W. D. Selective tumor targeting by the hypoxia-activated prodrug AQ4N blocks tumor growth and metastasis in preclinical models of pancreatic cancer. Clin. Cancer. Res. 2007, 13, 2216-2225.
    • (2007) Clin. Cancer. Res , vol.13 , pp. 2216-2225
    • Lalani, A.S.1    Alters, S.E.2    Wong, A.3    Albertella, M.R.4    Cleland, J.L.5    Henner, W.D.6
  • 8
    • 0036041236 scopus 로고    scopus 로고
    • Bioreductively activated antitumor N-oxides: The case of AQ4N, a unique approach to hypoxia-activated cancer chemotherapy
    • (b) Patterson, L. H. Bioreductively activated antitumor N-oxides: the case of AQ4N, a unique approach to hypoxia-activated cancer chemotherapy. Drug Metab. Rev. 2002, 34, 581-592.
    • (2002) Drug Metab. Rev , vol.34 , pp. 581-592
    • Patterson, L.H.1
  • 9
    • 0026642263 scopus 로고
    • The role of cytochrome P450 and cytochrome P450 reductase in the reductive bioactivation of the novel benzotriazine di-N-oxide hypoxic cytotoxin 3-amino-1,2,4-benzotriazine-1, 4-dioxide (SR 4233, WIN 59075) by mouse liver
    • (a) Walton, M. I.; Wolf, C. R.; Workman, P. The role of cytochrome P450 and cytochrome P450 reductase in the reductive bioactivation of the novel benzotriazine di-N-oxide hypoxic cytotoxin 3-amino-1,2,4-benzotriazine-1, 4-dioxide (SR 4233, WIN 59075) by mouse liver. Biochem. Pharmacol. 1992, 44, 251-259.
    • (1992) Biochem. Pharmacol , vol.44 , pp. 251-259
    • Walton, M.I.1    Wolf, C.R.2    Workman, P.3
  • 10
    • 85135112851 scopus 로고    scopus 로고
    • Sartorelli, A. C.; Hodnick, W. F.; Belcourt, M. F.; Tomasz, M.; Haffty, B.; Fischer, J. J.; Rockwell, S. Mitomycin C: a prototype bioreductive agent. Oncol. Res. 1994, 6, 501-508.
    • (b) Sartorelli, A. C.; Hodnick, W. F.; Belcourt, M. F.; Tomasz, M.; Haffty, B.; Fischer, J. J.; Rockwell, S. Mitomycin C: a prototype bioreductive agent. Oncol. Res. 1994, 6, 501-508.
  • 13
    • 0031803347 scopus 로고    scopus 로고
    • Inhibition of nitric oxide formation by neuronal nitric oxide synthase by quinones: Nitric oxide synthase as a quinone reductase
    • (c) Kumagai, Y.; Nakajima, H.; Midorikawa, K.; Homma-Takeda, S.; Shimojo, N. Inhibition of nitric oxide formation by neuronal nitric oxide synthase by quinones: nitric oxide synthase as a quinone reductase. Chem. Res. Toxicol. 1998, 11, 608-613.
    • (1998) Chem. Res. Toxicol , vol.11 , pp. 608-613
    • Kumagai, Y.1    Nakajima, H.2    Midorikawa, K.3    Homma-Takeda, S.4    Shimojo, N.5
  • 14
    • 0034691656 scopus 로고    scopus 로고
    • One-electron reduction of quinones by the neuronal nitric-oxide synthase reductase domain
    • (d) Matsuda, H.; Kimura, S.; Iyanagi, T. One-electron reduction of quinones by the neuronal nitric-oxide synthase reductase domain. Biochim. Biophys. Acta 2000, 1459, 106-116.
    • (2000) Biochim. Biophys. Acta , vol.1459 , pp. 106-116
    • Matsuda, H.1    Kimura, S.2    Iyanagi, T.3
  • 15
    • 33749169389 scopus 로고    scopus 로고
    • Inducible nitric oxide synthase and apoptosis in human B cell lymphomas
    • (a) Atik, E.; Ergin, M.; Erdogan, S.; Tuncer, I. Inducible nitric oxide synthase and apoptosis in human B cell lymphomas. Mol. Cell. Biochem. 2006, 290, 205-209.
    • (2006) Mol. Cell. Biochem , vol.290 , pp. 205-209
    • Atik, E.1    Ergin, M.2    Erdogan, S.3    Tuncer, I.4
  • 16
    • 0025302112 scopus 로고
    • Hormone-induced biosynthesis of endothelium-derived relaxing factor/nitric oxide-like material in N1E-115 neuroblastoma cells requires calcium and calmodulin
    • (b) Förstermann, U.; Gorksy, L. D.; Pollock, J. S.; Ishii, K.; Schmidt, H. H.; Heller, M.; Murad, F. Hormone-induced biosynthesis of endothelium-derived relaxing factor/nitric oxide-like material in N1E-115 neuroblastoma cells requires calcium and calmodulin. Mol. Pharmacol. 1990, 38, 7-13.
    • (1990) Mol. Pharmacol , vol.38 , pp. 7-13
    • Förstermann, U.1    Gorksy, L.D.2    Pollock, J.S.3    Ishii, K.4    Schmidt, H.H.5    Heller, M.6    Murad, F.7
  • 17
    • 0027974255 scopus 로고
    • Human colon cancer cell lines show a diverse pattern of nitric oxide synthase gene expression and nitric oxide generation
    • (c) Jenkins, D. C.; Charles, I. G.; Baylis, S. A.; Lelchuk, R.; Radomski, M. W.; Moncada, S. Human colon cancer cell lines show a diverse pattern of nitric oxide synthase gene expression and nitric oxide generation. Br. J. Cancer 1994, 70, 847-849.
    • (1994) Br. J. Cancer , vol.70 , pp. 847-849
    • Jenkins, D.C.1    Charles, I.G.2    Baylis, S.A.3    Lelchuk, R.4    Radomski, M.W.5    Moncada, S.6
  • 19
    • 0028873889 scopus 로고
    • Expression of nitric oxide synthase in human central nervous system tumors
    • (e) Cobbs, C. S.; Brenman, J. E.; Aldape, K. D.; Bredt, D. S.; Israel, M. A. Expression of nitric oxide synthase in human central nervous system tumors. Cancer Res. 1995, 55, 727-730.
    • (1995) Cancer Res , vol.55 , pp. 727-730
    • Cobbs, C.S.1    Brenman, J.E.2    Aldape, K.D.3    Bredt, D.S.4    Israel, M.A.5
  • 21
    • 0031740961 scopus 로고    scopus 로고
    • Nitric oxide synthase activity in fresh cells from ovarian tumour tissue: Relationship of enzyme activity with clinical parameters of patients with ovarian cancer
    • (g) Thomsen, L. L.; Sargent, J. M.; Williamson, C. J. H.; Elgie, A. W. Nitric oxide synthase activity in fresh cells from ovarian tumour tissue: relationship of enzyme activity with clinical parameters of patients with ovarian cancer. Biochem. Pharmacol. 1998, 56, 1365-1370.
    • (1998) Biochem. Pharmacol , vol.56 , pp. 1365-1370
    • Thomsen, L.L.1    Sargent, J.M.2    Williamson, C.J.H.3    Elgie, A.W.4
  • 22
    • 0028650760 scopus 로고
    • Aliphatic amine N-oxides of DNA binding agents as bioreductive drugs
    • (a) Patterson, L. H.; Craven, M. R.; Fisher, G. R.; Teesdale-Spittle, P. Aliphatic amine N-oxides of DNA binding agents as bioreductive drugs. Oncol. Res. 1994, 6, 533-538.
    • (1994) Oncol. Res , vol.6 , pp. 533-538
    • Patterson, L.H.1    Craven, M.R.2    Fisher, G.R.3    Teesdale-Spittle, P.4
  • 23
    • 0031040944 scopus 로고    scopus 로고
    • DNA topoisomerase II-dependent cytotoxicity of alkylaminoanthraquinones and their N- oxides
    • (b) Smith, P. J.; Blunt, J. N.; Desnoyers, R.; Giles, Y.; Patterson, L. H. DNA topoisomerase II-dependent cytotoxicity of alkylaminoanthraquinones and their N- oxides. Cancer Chemother. Pharmacol. 1997, 39, 455-461.
    • (1997) Cancer Chemother. Pharmacol , vol.39 , pp. 455-461
    • Smith, P.J.1    Blunt, J.N.2    Desnoyers, R.3    Giles, Y.4    Patterson, L.H.5
  • 24
    • 0031742538 scopus 로고    scopus 로고
    • Involvement of human hepatic cytochrome P450(CYP's) in the reductive metabolism of AQ4N, a novel anthraquinone based antineoplastic prodrug
    • (a) Raleigh, S. M.; Wanogho, E.; Burke, M. D.; McKeown, S. R.; Patterson, L. H. Involvement of human hepatic cytochrome P450(CYP's) in the reductive metabolism of AQ4N, a novel anthraquinone based antineoplastic prodrug. Int. J. Radiat. Oncol., Biol., Phys. 1998, 42, 763-767.
    • (1998) Int. J. Radiat. Oncol., Biol., Phys , vol.42 , pp. 763-767
    • Raleigh, S.M.1    Wanogho, E.2    Burke, M.D.3    McKeown, S.R.4    Patterson, L.H.5
  • 27
    • 50249092264 scopus 로고    scopus 로고
    • 13b
    • 13b
  • 28
    • 50249091202 scopus 로고    scopus 로고
    • Solubility of Selected Gases in Water
    • 88th ed, Lide D. R, Ed, CRC Press: Boca Raton, FL, Chapter 8, pp
    • (b) Gevantman, L. H. Solubility of Selected Gases in Water. In CRC Handbook of Chemistry and Physics, 88th ed.; Lide D. R., Ed.; CRC Press: Boca Raton, FL, 2007; Chapter 8, pp 80-83.
    • (2007) CRC Handbook of Chemistry and Physics , pp. 80-83
    • Gevantman, L.H.1
  • 29
    • 0025787205 scopus 로고
    • Purification and characterization of the cytokine-induced macrophage nitric oxide synthase: An FAD- and FMN-containing flavoprotein
    • Stuehr, D. J.; Cho, H. J.; Kwon, N. S.; Weise, M. F.; Nathan, C. F. Purification and characterization of the cytokine-induced macrophage nitric oxide synthase: an FAD- and FMN-containing flavoprotein. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 7773-7777.
    • (1991) Proc. Natl. Acad. Sci. U.S.A , vol.88 , pp. 7773-7777
    • Stuehr, D.J.1    Cho, H.J.2    Kwon, N.S.3    Weise, M.F.4    Nathan, C.F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.