In vitro metabolism study of the promising anticancer agent the lignan (-)-grandisin

Journal of Pharmaceutical and Biomedical Analysis

Volumn 72, Issue , 2013, Pages 240-244

  Messiano, Gisele Baraldi ^a   Santos, Renan Augusto da Silva ^a   Ferreira, Leandro De Santis ^a   Simões, Rodrigo Almeida ^a,b   Jabor, Valquíria Aparecida Polisel ^a   Kato, Massuo Jorge ^a   Lopes, Norberto Peporine ^a   Pupo, Mônica Tallarico ^a   de Oliveira, Anderson Rodrigo Moraes ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF SERGIPE   (Brazil)

Author keywords

CYP450; Dihydro grandisin metabolite; Grandisin; In vitro metabolism; Method validation; Rat liver microsomes

Indexed keywords

ANTINEOPLASTIC AGENT; CYTOCHROME P450; GRANDISIN; LIGNAN; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANTIANGIOGENIC ACTIVITY; ANTIBACTERIAL ACTIVITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; DRUG STRUCTURE; DRUG TRANSFORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; LIVER MICROSOME; MALE; MASS FRAGMENTOGRAPHY; MICHAELIS MENTEN KINETICS; NONHUMAN; PRIORITY JOURNAL; RAT; VALIDATION PROCESS;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FURANS; KINETICS; LIGNANS; MALE; MICROSOMES, LIVER; RATS; RATS, WISTAR;

EID: 84869093673     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.08.028     Document Type: Article

References (27)

1. Lopes N.P., Kato M.J., Yoshida M. Antifungal constituents from roots of Virola surinamensis. Phytochemistry 1999, 51:23-33.
2. Morais S.K.R., Teixeira A.F., Torres Z.E.S., Nunomura S.M., Kanashiro E.H.Y., Lindoso J.A.L., Yoshida M. Biological activities of lignoids from Amazon Myristicaceae species: Virola michelii, V. mollissima, V. pavonis and Iryanthera juruensis. J. Braz. Chem. Soc. 2009, 20:1110-1118.
3. Pu J.X., Gao X.M., Lei C., Xiao W.L., Wang R.R., Yang L.B., Zhao Y., Li L.M., Huang S.X., Zheng Y.T., Sun H.D. Three new compounds from Kadura longipedunculata. Chem. Pharm. Bull. 2008, 56:1143-1146.
4. Cabral M.M.O., Alencar J.A., Guimarães A.E., Kato M.J. Larvicidal activity of grandisin against Aedes aegypti. J. Am. Mosq. Control. Assoc. 2009, 25:103-105.
5. Bernardes L.S.C., Kato M.J., Albuquerque S., Carvalho I. Synthesis and trypanocidal activity of 1,4-bis-(3,4,5-trimethoxy-phenyl)-1,4-butanediol and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol. Bioorg. Med. Chem. 2006, 14:7075-7082.
6. Martins R.C.C., Lago J.H.G., Albuquerque S., Kato M.J. Trypanocidal tetrahydrofuran lignans from inflorescences of Piper solmsianum. Phytochemistry 2003, 64:667-670.
7. de Oliveira R.B., Vaz A.B.M., Alves R.O., Liarte D.B., Donnici C.L., Romanha A.J., Zani C.L. Arylfurans as potential Trypnosoma cruzi trypanothione reductase inhibitors. Mem. Inst. Oswaldo Cruz 2006, 101:169-173.
8. Carvalho A.A.V., Galdino P.M., Nascimento M.V.M., Kato M.J., Valadares M.C., Cunha L.C., Costa E.A. Antinoceptive and anti-inflammatory activities of grandisin extracted from Virola surinamensis. Phytother. Res. 2010, 24:113-118.
9. Valadares M.C., de Carvalho I.C.T., Junior L.O., Vieira M.S., Benfica P.L., de Carvalho F.S., Andrade L.V.S., Lima E.M., Kato M.J. Citotoxicity and angiogenic activity of grandisin. J. Pharm. Pharmacol. 2009, 61:1709-1714.
10. Valadares M.C., Júnior L.M.O., de Carvalho F.S., Andrade L.V.S., dos Santos A.P., de Oliveira V., Gil E.S., Kato M.J. Chemoprotective effect of the tetrahydrofuran lignan grandisin in the in vivo rodend micronucleus assay. J. Pharm. Pharmacol. 2011, 63:447-451.
11. Vieira M.S., de Oliveira V., Lima E.M., Kato M.J., Valadares M.C. In vitro basal cytotoxicity assay applied to estimate cute oral systemic toxicity of grandisin and its major metabolite. Exp. Toxicol. Pathol. 2011, 63:505-510.
12. Riley R.J., Grime K. Metabolic screening in vitro: metabolic stability CYP inhibition and induction. Drug Discov. Today Technol. 2004, 1:365-372.
13. Lipscomb J.C., Poet T.S. In vitro measurements of metabolism for application in pharmacokinetic modeling. Pharmacol. Therapeut. 2008, 118:82-103.
14. Brandon E.F.A., Raap C.D., Meijerman I., Beijnen J.H., Schellens J.H.M. An update on in vitro test methods in human hepatic drug biotransformation research: pros and cons. Toxicol. Appl. Pharmacol. 2003, 189:233-246.
15. Fasinu P., Bouic P.J., Rosenkranz B. Liver-based in vitro technologies for drug biotransformation studies - a review. Curr. Drug Metabol. 2010, 13:215-224.
16. Atkins W.M. Implications of the allosteric kinetics of cytochrome P450s. Drug Discov. Today 2004, 9:478-484.
17. Plant N. Strategies for using in vitro screens in drug metabolism. Drug Discov. Today 2004, 9:328-336.
18. Martins R.C.C., Latorre L.R., Sartorelli P., Kato M.J. Phenylpropanoids and tetrahydrofuran lignans from Piper solmsianum. Phytochemistry 2000, 55:843-846.
19. Almeida A.M., Castel-Branco M.M., Falcão A.C. Linear regression for calibration lines revisited: weighting schemes for bioanalytical methods. J. Chromatogr. 2002, B774:215-222.
20. Guidance for Industry: Bioanalytical Method Validation, Center for Drug Evaluation and Research, United States Food and Drug Administration. (accessed 15.02.12). http://www.fda.gov/cder/guidance/index.htm.
21. Kobayashi K., Urashima K., Shimada N., Chiba K. Substrate specificity rat cytochrome P450 (CYP) isoforms: screening with cDNA-expressed systems on the rat. Biochem. Pharmacol. 2002, 63:889-896.
22. Brown C.M., Reisfeld B., Mayeno A.N. Cytochromes P450: a structure-based summary of biotransformations using representative substrates. Drug Metabol. Rev. 2008, 40:1-100.
23. Verza M., Arakawa N.S., Lopes N.P., Kato M.J., Pupo M.T., Said S., Carvalho I. Biotransformation of a tetrahydrofuran lignan by endophytic fungus Phomopsis sp. J. Braz. Chem. Soc. 2009, 20:195-200.
24. Ramos C.S., Vanin S.A., Kato M.J. Metabolism of (-)-grandisin from Piper solmsianum in Coleoptera and Lepidoptera species. Phytochemistry 2008, 69:2157-2161.
25. L.S. Ferreira, D.R. Callejon, A. Engemann, B. Cramer, H.U. Humpf, V.P. Barros, M.D. Assis, S. Albuquerque, L.T. Okano, M.J. Kato, N.P. Lopes, Evaluation of Grandisin in vitro metabolism, a lignan with anti-chagasic activity. Planta Med., in press.
26. Pearson J., Dahal U.P., Rock D., Peng C., Schenk J.O., Joswig-Jones C., Jones J.P. The kinetic mechanism for cytochrome P450 metabolism of Type II binding compounds: Evidence supporting direct reduction. Arch. Biochem. Biophys. 2011, 511:69-79.
27. MacLeod T.C.O., Faria A.L., Barros V.P., Queiroz M.E.C., Assis M.D. Primidone oxidation catalyzed by metalloporphyrins and Jacobsen catalyst. J. Mol. Catal. A: Chem. 2008, 296:54-60.