Modulation of activity profiles for largazole-based HDAC inhibitors through alteration of prodrug properties

ACS Medicinal Chemistry Letters

Volumn 5, Issue 8, 2014, Pages 905-910

  Salvador, Lilibeth A ^a,d   Park, Heekwang ^b   Al Awadhi, Fatma H ^a   Liu, Yanxia ^a   Kim, Bumki ^b   Zeller, Sabrina L ^b   Chen, Qi Yin ^a   Hong, Jiyong ^b,c   Luesch, Hendrik ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b DUKE UNIVERSITY   (United States)

^c DUKE UNIVERSITY MEDICAL CENTER   (United States)

^d University of the Philippines Diliman   (Philippines)

Author keywords

antitumor activity; histone deacetylases; Largazole; natural products; prodrugs

Indexed keywords

ANTINEOPLASTIC AGENT; HISTONE DEACETYLASE INHIBITOR; LARGAZOLE DERIVATIVE; PRODRUG; ROMIDEPSIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL; CELL MEMBRANE PERMEABILITY; CELL PROLIFERATION; DRUG BIOAVAILABILITY; DRUG DOSE INCREASE; DRUG PENETRATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; DRUG TUMOR LEVEL; ENZYME ACTIVITY; ENZYME INHIBITION; HCT116 CELL LINE; HISTONE ACETYLATION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IN VIVO STUDY; MODULATION; MOUSE; NONHUMAN; PRIORITY JOURNAL;

EID: 84906278350     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml500170r     Document Type: Article

References (24)

1. Sharma, S.; Kelly, T. K.; Jones, P. A. Epigenetics in cancer Carcinogenesis 2010, 31, 27-36
2. 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
3. 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
4. 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, 2013; pp 59-95.
5. 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
6. Harrison, S. J.; Bishton, M.; Bates, S. E.; Grant, S.; Piekarz, R. L.; Johnstone, R. W.; Dai, Y.; Lee, B.; Araujo, M. E.; Prince, H. M. A focus on the preclinical development and clinical status of the histone deacetylase inhibitor, romidepsin (depsipeptide, Istodax) Epigenomics 2012, 4, 571-589
7. Bolden, J.; Peart, M. J.; Johnstone, R. W. Anticancer activities of histone deacetylase inhibitors Nat. Rev. Drug Discovery 2006, 5, 769-784
8. Taunton, J.; Collins, J. L.; Schreiber, S. L. Synthesis of natural and modified trapoxins, useful reagents for exploring histone deacetylase function J. Am. Chem. Soc. 1996, 118, 10412-10422
9. Masuoka, Y.; Shindoh, N.; Inamura, N. Histone deacetylase inhibitors from microorganisms: The Astellas experience. In Progress in Drug Research; Amstutz, R.; Petersen, F., Eds.; Birkhauser Verlag: Basel, Switzerland, 2008; pp 337-359.
10. Nishino, N.; Jose, B.; Okamura, S.; Ebisusaki, S.; Kato, T.; Sumida, Y.; Yoshida, M. Cyclic tetrapeptides bearing a sulfhydryl group potently inhibit histone deacetylases Org. Lett. 2003, 5, 5079-5082
11. Shivashimpi, G. M.; Amagai, S.; Kato, T.; Nishino, N.; Maeda, S.; Nishino, T. G.; Yoshida, M. Molecular design of histone deacetylase inhibitors by aromatic ring shifting in chlamydocin framework Bioorg. Med. Chem. 2007, 15, 7830-7839
12. Sasaki, K.; Ito, T.; Nishino, N.; Khochbin, S.; Yoshida, M. Real-time imaging of histone H4 hyperacetylation in living cells Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 16257-16262
13. 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
14. Hong, J.; Luesch, H. Largazole: from discovery to broad-spectrum therapy Nat. Prod. Rep. 2012, 29, 449-456
15. 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
16. 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
17. 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
18. Yu, M.; Salvador, L. A.; Sy, S. K. B.; Tang, Y.; Singh, R. S. P.; Chen, Q.-Y.; Liu, Y.; Hong, J.; Derendorf, H.; Luesch, H. Largazole pharmacokinetics in rats by LC-MS/MS Mar. Drugs 2014, 12, 1623-1640
19. Law, M. E.; Corsino, P. E.; Jahn, S. C.; Davis, B. J.; Chen, S.; Patel, B.; Pham, K.; Lu, J.; Sheppard, B.; Nørgaard, P.; Hong, J.; Higgins, P.; Kim, J.-S.; Luesch, H.; Law, B. K. Glucocorticoids and histone deacetylase inhibitors cooperate to block the invasiveness of basal-like breast cancer cells through novel mechanisms Oncogene 2013, 32, 1316-1329
20. Bowers, A.; West, N.; Taunton, J.; Schreiber, S. L.; Bradner, J. E.; Williams, R. M. Total synthesis and biological mode of action of largazole: a potent class I histone deacetylase inhibitor J. Am. Chem. Soc. 2008, 130, 11219-11222
21. Kamber, B.; Hartmann, A.; Eisler, K.; Riniker, B.; Rink, H.; Sieber, P.; Rittel, W. The synthesis of cystine peptides by iodine oxidation of S -trityl-cysteine and S -acetamidomethyl-cysteine peptides Helv. Chim. Acta 1980, 63, 899-915
22. Veber, D. F.; Johnson, S. R.; Cheng, H. Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular properties that influence the oral bioavailability of drug candidates J. Med. Chem. 2002, 45, 2615-2623
23. Li, Z.; Chan, K. K. A subnanogram API LC/MS/MS quantitation method for depsipeptide FR901228 and its preclinical pharmacokinetics J. Pharm. Biomed. Anal. 2000, 22, 33-44
24. 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.