Effect of 2-(4-aminophenylmethyl)-6-hydroxy-3,4-dihydronaphthalen-1(2H)-one on all-trans and 13-cis-retinoic acid levels in plasma quantified by high perfomance liquid chromatography coupled to tandem mass spectrometry

References

• Bollag W In: Saurat TH, editor. Retinoids: New trends in research and therapy. Basle: Karger; 1985. p 274.
   Google Scholar
• Van Wauwe JP, Coene MC, Goossens J, Van Nyen G, Cools W, Lauwers W. Ketoconazole inhibits the in vitro and in vivo metabolism of all-trans-retinoic acid. J Pharmacol Exp Ther 1988;245(2):718–722.
   PubMed Web of Science ®Google Scholar
• Van Wauwe JP, Coene MC, Goossens J, Van Nyen G, Cools W, Lauwers W. Effect of cytochrome P-450 inhibitors on the in vivo metabolism of all trans-retinoic acid. J Pharmacol Exp Ther 1990;252(1):365–369.
   PubMed Web of Science ®Google Scholar
• Leo MA, Lida S, Lieber CS. Retinoic acid metabolism by a system reconstituted with cytochrome P450. Arch Biochem Biophys 1984;234:305–312.
   PubMed Web of Science ®Google Scholar
• Leo MA, Lasker Jl, Raucy JL, Cho-il K, Black M, Lieber CS. Metabolism of retinol and retinoic acid by human liver cyto- chrome P450 IIC8. Arch Biochem Biophys 1989;15:305–312.
   Google Scholar
• Roberts ES, Vaz ADN, Coon MJ. Role of isozymes of rabbit microsomal cytochrome P450 in the metabolism of retinoic acid, retinol and retinal. Mol Pharmacol 1992;41:427–433.
   PubMed Web of Science ®Google Scholar
• Martini R, Murray M. Participation of P4503A enzymes in rat hepatic microsomal retinoic acid 4-hydroxylation. Arch Biochem Biophys 1993;303:17–66.
   Web of Science ®Google Scholar
• Raner GM, Vaz ADN, Coon MJ. Metabolism of all-trans, 9-cis and 13-cis isomers of retinal by purified isozymes of microsomal cytochrome P450 and mechanism-based inhi- bition of retinoic oxidation by citral. Mol Pharmacol 1996; 49:515–522.
   PubMed Web of Science ®Google Scholar
• White JA, Beckett-Jones B, Guo YD, Dilworth J, Bonasoro J, Jones G, Petkovich M. cDNA cloning of human retinoic acid- metabolizing enzyme (hP450RAI) identifies a novel family of cytochromes P450 (CYP26). J Biol Chem 1997;272:18538–18541.
   PubMed Web of Science ®Google Scholar
• White JA, Guo YD, Baetz K, Beckett-Jones B, Bonasoro J, Hsu KE, Dilworth J, Jones G, Petkovich M. Identification of the retinoic acid-inducible all-trans-retinoic acid 4-hydroxylase. J Biol Chem 1996;271:29922–29927.
   PubMed Web of Science ®Google Scholar
• Smith HJ, Nicholls PJ, Simons C, LeLain R. Inhibitors of steroidogenesis as agents for the treatment of hormone- dependent cancers. Exp Opin Ther Pat 2001;11:789–824.
   Web of Science ®Google Scholar
• Kuijpers A, Van Pelt J, Bergers M, Boegheim P, Den Bakker J, Siegenthaler G, Van de Kerkhof P, Schalkwijk J. The effect of oral liarozole on epidermal proliferation and differentiation in severe plaque psoriasis are comparable with those of acitretin. Br J Dermatol 1998;139:380–389.
   PubMed Web of Science ®Google Scholar
• Van Pelt J, De Jong E, De Bakker E, Van de Kerkhof P. Effects of systemic treatment with liarozole on cutaneous inflam- mation, epidermal proliferation and differentiation in exten- sive plaque psoriasis. Skin Pharmacol Appl Skin Physiol 1998;11:70–79.
   PubMedGoogle Scholar
• Dijkman GA, Fernandex del Moral P, Bruynseels J, De Porte P, Denis L, Debruyne F. Liarozole (R75251) in hormone- resistant prostate cancer patients. Prostate 1997;33:26–31.
   Google Scholar
• Debruyne R, Murray R, Fradet Y, Johansson JE, Tyrrell C, Boccardo F, Denis L, Marberger JM, Brune D, Rassweler J, Vangeneugden T, Bruynseels J, Janssens M, De Porre P. Liarozole-A novel treatment approach for advanced prostate cancer: Results of a large randomized trial versus cyproterone acetate. Urology 1998;52:72–81.
   PubMed Web of Science ®Google Scholar
• Denis L, Debruyne F, De Porre P, Bruynseels J. Early clinical experience with liarozole (Liazal(TM)) in patients with progressive prostate cancer. Eur J Cancer 1998;34:469–475.
   PubMed Web of Science ®Google Scholar
• Miller W. The emerging role of retinoids and retinoic acid metabolism blocking agents in the treatment of cancer. Cancer 1998;83:1471–1482.
   PubMed Web of Science ®Google Scholar
• O’Bryne KJ, Han C, Mitchell K, Lane D, Carmichael J, Harris AI, Talbot DC. Phase II study of liarozole in advanced non- small cell lung cancer. Eur J Cancer 1998;34:1463–1466.
   PubMedGoogle Scholar
• Schwartz EL, Hallam S, Gallagher RE, Wiernik PH. Inhibition of all-trans-retinoic acid metabolism by fluconazole in vitro and in patients with acute promyelocytic leukaemia. Biochem Pharmacol 1995;50:923–928.
   PubMed Web of Science ®Google Scholar
• Stoppie P, Borgers M, Borghgraef P, Dillen L, Goossens J, Sanz G, Szel H, Van Hove C, Van Nyen G, Nobels G, Vanden Bossche H, Venet M, Willemsens G, Van Wauwe J. R115866 inhibits all-trans-retinoic acid metabolism and exerts retinoi- dal effects in rodents. J Pharmacol Exp Ther 2000;293:304–312.
   PubMed Web of Science ®Google Scholar
• Le Borgne M, Marchand P, Le Baut G, Ahmadi M, Smith HJ, Nicholls PJ. Retinoic acid metabolism inhibition by 3-azoly- methyl-1H-indoles and 2,3 or 5-(a-azolylbenzyl)-1H-indoles. J Enz Inhib Med Chem 2003;18:155–158.
   PubMed Web of Science ®Google Scholar
• Kirby AJ, LeLain R, Maharlouie F, Mason P, Nicholls PJ, Smith HJ, Simons C. Inhibition of retinoic acid metabolising enzymes by 2-(4-aminophenylmethyl)-6-hydroxy-3,4-di- hydronaphthalen-1(2H)-one and related compounds. J Enz Inhib Med Chem 2003; 18:27-33;Smith H J, Ahmadi M, Nicholls P J, Hassanzadeh M F, Benzyl and Benzylidene tetralins and derivatives. WO 9935115 (1999-07-15).
   Google Scholar
• Nijar VCO. Cyrochrome P-450 retinoic acid 4-hydroxylase inhibitors: potential agents for cancer therapy. Mini Rev Med Chem 2002;2:261–269.
   PubMed Web of Science ®Google Scholar
• Nadin L, Murray M. Participation of CYP2C8 in retinoic acid 4-hydroxylation in human hepatic microsomes. Biochem Pharmacol 1999;58:1201–1208.
   PubMed Web of Science ®Google Scholar
• Marill J, Cresteil T, Lanotte M, Chabot GG. Identification of human cytochrome P450s involved in the formation of all- trans-retinoic acid principal metabolites. Mol Pharmacol 2000;58:1341–1348.
   PubMed Web of Science ®Google Scholar
• McSorley LC, Daly AK. Identification of human cytochrome P450 isoforms that contribute to all-trans-retinoic acid 4-hydroxylation. Biochem Pharmacol 2000;60:517–526.
   PubMed Web of Science ®Google Scholar
• Ray WJ, Bain G, Yao M, Gottlieb DI. CYP26, a novel mammalian cytochrome P450 is induced by retinoic acid and defines a new family. J Biol Chem 1997; 272:18702–18708.
   PubMed Web of Science ®Google Scholar
• Haque M, Andreola F, DeLuca LM. The cloning and characterisation of a novel cytochrome P450 family, CYP26 with specificity toward retinoic acid. Nutrition Rev 1998;56:84 –85.
   Google Scholar
• Marikar Y, Wang Z, Duell EA, Petkovich M, Voorhees JJ, Fisher GJ. Retinoic acid receptors regulate expression of retinoic acid 4-hydroxylase that specifically inactivates all-trans retinoic acid in human keratinocyte HaCat cells. J Invest Dermatol 1998;111:434–439.
   PubMed Web of Science ®Google Scholar
• Luu L, Ramshaw H, Tahayato A, Stuart A, Jones G, White J, Petkovich M. Regulation of retinoic acid metabolism. Adv Enzyme Reg 2001;41:159–175.
   PubMedGoogle Scholar
• Popa C, Dicker AJ, Dahler A, Saunders NA. Cytochrome P450, CYP26A1, is expressed at low levels in human epidermal keratinocytes and is not retinoic acid inducible. Br J Dermatol 1999;141:460–468.
   PubMed Web of Science ®Google Scholar
• Gundersen TE, Blomhoff R. Qualitative and quantitative liquid chromatographic determination of natural retinoids in biological samples. J Chromatogr A 2001;935:13–43.
   PubMed Web of Science ®Google Scholar
• Lanvers G, Hempel G, Blashke G, Boos J. Simultaneous determination of all-trans-, 13-cis- and 9-cis-retinoic acid, their 4-oxo metabolites and all-trans-retinol in human plasma by high-performance liquid chromatography. J Chromatogr B 1996;685:233–240.
   PubMed Web of Science ®Google Scholar
• Wand Y, Chang WY, Prins GS, van Breemen RB. Simul- taneous determination of all-trans, 9-cis, 13-cis-retinoic acid and retinol in rat prostate using liquid chromatography-mass- spectrometry. J Mass Spectrom 2001;36:882–888.
   PubMed Web of Science ®Google Scholar