Largazole pharmacokinetics in rats by LC-MS/MS

Marine Drugs

Volumn 12, Issue 3, 2014, Pages 1623-1640

  Yu, Mingming ^a,d   Salvador, Lilibeth A ^a,e   Sy, Sherwin K B ^a   Tang, Yufei ^a   Singh, Ravi S P ^a   Chen, Qi Yin ^a,b   Liu, Yanxia ^a,b   Hong, Jiyong ^c   Derendorf, Hartmut ^a,b   Luesch, Hendrik ^a,b  

^a UNIVERSITY OF FLORIDA HEALTH   (United States)

^b UNIVERSITY OF FLORIDA   (United States)

^c DUKE UNIVERSITY   (United States)

^d OCEAN UNIVERSITY OF CHINA   (China)

^e University of the Philippines Diliman   (Philippines)

Author keywords

Largazole; LC MS MS; Pharmacokinetics; Protein binding

Indexed keywords

HARMINE; HISTONE DEACETYLASE INHIBITOR; LARGAZOLE THIOL; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ACCURACY; ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CALIBRATION; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG ELIMINATION; DRUG HALF LIFE; DRUG ISOLATION; DRUG PROTEIN BINDING; HUMAN; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; MAXIMUM PLASMA CONCENTRATION; MEAN RESIDENCE TIME; NONHUMAN; PROCESS DEVELOPMENT; PRODUCT RECOVERY; QUANTITATIVE ANALYSIS; RAT; SENSITIVITY AND SPECIFICITY; VALIDATION PROCESS;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEPSIPEPTIDES; HALF-LIFE; HISTONE DEACETYLASE INHIBITORS; HUMANS; INDICATORS AND REAGENTS; MALE; MASS SPECTROMETRY; PLASMA; PROTEIN BINDING; QUALITY CONTROL; RATS; RATS, SPRAGUE-DAWLEY; REPRODUCIBILITY OF RESULTS; THIAZOLES;

EID: 84897099358     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12031623     Document Type: Article

References (35)

1. Taori, K.; Paul, V.J.; Luesch, H. Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp. J. Am. Chem. Soc. 2008, 130, 1806-1807. (Pubitemid 351238618)
2. Liu, Y.; Salvador, L.A.; Byeon, S.; Ying, Y.; Kwan, J.C.; Law, B.K.; Hong, J.; Luesch, H. Anticolon cancer activity of largazole, a marine-derived tunable histone deacetylase inhibitor. J. Pharmacol. Exp. Ther. 2010, 335, 351-361.
3. Bowers, A.; West, N.; Taunton, J.; Schreiber, S.L.; Bradner, J.E.; Williams, R.M. The Total Synthesis and biological mode of action of largazole: A potent class I histone deacetylase (HDAC) inhibitor. J. Am. Chem. Soc. 2008, 130, 11219-11222.
4. Hong, J.; Luesch, H. Largazole: from discovery to broad-spectrum therapy. Nat. Prod. Rep. 2012, 29, 449-456.
5. Ying, Y.; Taori, K.; Kim, H.; Hong, J.; Luesch, H. Total synthesis and molecular target of largazole, a histone deacetylase inhibitor. J. Am. Chem. Soc. 2008, 130, 8455-8459. (Pubitemid 351898566)
6. Nasveschuk, C.G.; Ungermannova, D.; Liu, X.; Phillips, A.J. A concise total synthesis of largazole, solution structure, and some preliminary structure activity relationships. Org. Lett. 2008, 10, 3595-3598.
7. Ren, Q.; Dai, L.; Zhang, H.; Tan, W.; Xu, Z.; Ye, T. Total synthesis of largazole. Synlett 2008, 2008, 2379-2383.
8. Xiao, Q.; Wang, L.-P.; Jiao, X.-Z.; Liu, X.-Y.; Wu, Q.; Xie, P. Concise total synthesis of largazole. J. Asian Nat. Prod. Res. 2010, 12, 940-949.
9. Seiser, T.; Kamena, F.; Cramer, N. Synthesis and biological activity of largazole and derivatives. Angew. Chem. Int. Ed. Engl. 2008, 47, 6483-6485.
10. Zeng, X.; Yin, B.; Hu, Z.; Liao, C.; Liu, J.; Li, S.; Li, Z.; Nicklaus, M.C.; Zhou, G.; Jiang, S. Total synthesis and biological evaluation of largazole and derivatives with promising selectivity for cancers cells. Org. Lett. 2010, 12, 1368-1371.
11. Wang, B.; Forsyth, C. Total synthesis of largazole - devolution of a novel synthetic strategy. Synthesis 2009, 2009, 2873-2880.
12. Benelkebir, H.; Marie, S.; Hayden, A.L.; Lyle, J.; Loadman, P.M.; Crabb, S.J.; Packham, G.; Ganesan, a Total synthesis of largazole and analogues: HDAC inhibition, antiproliferative activity and metabolic stability. Bioorg. Med. Chem. 2011, 19, 3650-3658.
13. Numajiri, Y.; Takahashi, T.; Takagi, M.; Shin-ya, K.; Doi, T. Total synthesis of largazole and its biological evaluation. Synlett 2008, 2008, 2483-2486.
14. Ghosh, A.K.; Kulkarni, S. Enantioselective total synthesis of (+)-largazole, a potent inhibitor of histone deacetylase. Org. Lett. 2008, 10, 3907-3909.
15. Cole, K.E.; Dowling, D.P.; Boone, M.A.; Phillips, A.J.; Christianson, D.W. Structural basis of the antiproliferative activity of largazole, a depsipeptide inhibitor of the histone deacetylases. J. Am. Chem. Soc. 2011, 133, 12474-12477.
16. Salvador, L.; Luesch, H. HDAC Inhibitors and Other Histone Modifying Natural Products as Emerging Anticancer Agents. In Natural Products and Cancer Drug Discovery; Koehn, F.E., Ed.; Springer: New York, NY, USA, 2013; pp. 59-95.
17. Halkidou, K.; Gaughan, L.; Cook, S.; Leung, H.Y.; Neal, D.E.; Robson, C.N. Upregulation and nuclear recruitment of HDAC1 in hormone refractory prostate cancer. Prostate 2004, 59, 177-189. (Pubitemid 38481229)
18. Nakagawa, M.; Oda, Y.; Eguchi, T.; Aishima, S.-I.; Yao, T.; Hosoi, F.; Basaki, Y.; Ono, M.; Kuwano, M.; Tanaka, M.; Tsuneyoshi, M. Expression profile of class I histone deacetylases in human cancer tissues. Oncol. Rep. 2007, 18, 769-774.
19. Song, J.; Noh, J.H.; Lee, J.H.; Eun, J.W.; Ahn, Y.M.; Kim, S.Y.; Lee, S.H.; Park, W.S.; Yoo, N.J.; Lee, J.Y.; Nam, S.W. Increased expression of histone deacetylase 2 is found in human gastric cancer. APMIS 2005, 113, 264-268. (Pubitemid 40676807)
20. Marks, P.A.; Breslow, R. Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug. Nat. Biotechnol. 2007, 25, 84-90. (Pubitemid 46087907)
21. Law, M.E.; Corsino, P.E.; Jahn, S.C.; Davis, B.J.; Chen, S.; Patel, B.; Pham, K.; Lu, J.; Sheppard, B.; Nørgaard, P.; et al. Glucocorticoids and histone deacetylase inhibitors cooperate to block the invasiveness of basal-like breast cancer cells through novel mechanisms. Oncogene 2013, 32, 1316-1329.
22. Lee, S.-U.; Kwak, H.B.; Pi, S.-H.; You, H.-K.; Byeon, S.R.; Ying, Y.; Luesch, H.; Hong, J.; Kim, S.H. In vitro and in vivo osteogenic activity of largazole. ACS Med. Chem. Lett. 2011, 2, 248-251.
23. Liu, Y.; Wang, Z.; Wang, J.; Lam, W.; Kwong, S.; Li, F.; Friedman, S.L.; Zhou, S.; Ren, Q.; Xu, Z.; et al. A histone deacetylase inhibitor, largazole, decreases liver fibrosis and angiogenesis by inhibiting transforming growth factor-β and vascular endothelial growth factor signaling. Liver Int. 2013, 33, 504-515.
24. FDA Pharmacology Toxicology Review and Evaluation of Romidepsin. Available online: http://www.accessdata.fda.gov/drugsatfda-docs/nda/2009/ 022393s000-PharmR-P2.pdf (accessed on 20 December 2013).
25. Furumai, R.; Matsuyama, A.; Kobashi, N.; Lee, K.-H.; Nishiyama, M.; Nakajima, H.; Tanaka, A.; Komatsu, Y.; Nishino, N.; Yoshida, M.; Horinouchi, S. FK228 (depsipeptide) as a natural prodrug that inhibits class I histone deacetylases. Cancer Res. 2002, 62, 4916-4921. (Pubitemid 34984414)
26. Kantharaj, E.; Jayaraman, R. Histone Deacetylase Inhibitors as Therapeutic Agents for Cancer Therapy: Drug Metabolism and Pharmacokinetic Properties. In Drug Development - A Case Study Based Insight into Modern Strategies; Rundfeldt, C., Ed.; InTech: Rijeka, Croatia, 2011; pp. 101-111.
27. Combes, F.P.; Retout, S.; Frey, N.; Mentré, F. Prediction of shrinkage of individual parameters using the bayesian information matrix in non-linear mixed effect models with evaluation in pharmacokinetics. Pharm. Res. 2013, 30, 2355-2367.
28. Chan, K.K.; Bakhtiar, R.; Jiang, C. Depsipeptide (FR901228, NSC-630176) pharmacokinetics in the rat by LC/MS/MS. Invest. New Drugs 1997, 15, 195-206. (Pubitemid 27453874)
29. Masuoka, Y.; Shindoh, N.; Inamura, N. Histone deacetylase inhibitors from microorganisms: The Astellas experience. Fortschr. Arzneimittelforsch. 2008, 66, 335, 337-359.
30. Migdalof, B.H.; Antonaccio, M.J.; McKinstry, D.N.; Singhvi, S.M.; Lan, S.J.; Egli, P.; Kripalani, K.J. Captopril: Pharmacology, metabolism and disposition. Drug Metab. Rev. 1984, 15, 841-869.
31. Kubo, M.; Mizooku, Y.; Hirao, Y.; Osumi, T. Development and validation of an LC-MS/MS method for the quantitative determination of aripiprazole and its main metabolite, OPC-14857, in human plasma. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2005, 822, 294-299. (Pubitemid 40994064)
32. Koseki, N.; Kawashita, H.; Hara, H.; Niina, M.; Tanaka, M.; Kawai, R.; Nagae, Y.; Masuda, N. Development and validation of a method for quantitative determination of valsartan in human plasma by liquid chromatography-tandem mass spectrometry. J. Pharm. Biomed. Anal. 2007, 43, 1769-1774. (Pubitemid 46453072)
33. Viswanathan, C.T.; Bansal, S.; Booth, B.; DeStefano, A.J.; Rose, M.J.; Sailstad, J.; Shah, V.P.; Skelly, J.P.; Swann, P.G.; Weiner, R. Quantitative bioanalytical methods validation and implementation: best practices for chromatographic and ligand binding assays. Pharm. Res. 2007, 24, 1962-1973. (Pubitemid 47389236)
34. De Moraes, N.V.; Lauretti, G.R.; Napolitano, M.N.; Santos, N.R.; Godoy, A.L.; Lanchote, V.L. Enantioselective analysis of unbound tramadol, O-desmethyltramadol and N-desmethyltramadol in plasma by ultrafiltration and LC-MS/MS: application to clinical pharmacokinetics. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2012, 880, 140-147.
35. Pillai, G.C.; Mentré, F.; Steimer, J.-L. Non-linear mixed effects modeling-from methodology and software development to driving implementation in drug development science. J. Pharmacokinet. Pharmacodyn. 2005, 32, 161-183. (Pubitemid 41712738)