Systematic chemical mutagenesis identifies a potent novel apratoxin A/E hybrid with improved in vivo antitumor activity

ACS Medicinal Chemistry Letters

Volumn 2, Issue 11, 2011, Pages 861-865

  Chen, Qi Yin ^a   Liu, Yanxia ^a   Luesch, Hendrik ^a  

^a UNIVERSITY OF FLORIDA   (United States)

Author keywords

Antitumor agents; growth factors; natural products; receptor tyrosine kinases; secretory pathway; total synthesis

Indexed keywords

ALANINE; ANTINEOPLASTIC AGENT; APRATOXIN A; APRATOXIN E; APRATOXIN S4; BETA ACTIN; GROWTH FACTOR; NATURAL PRODUCT; PLATELET DERIVED GROWTH FACTOR BETA RECEPTOR; PROTEIN TYROSINE KINASE; UNCLASSIFIED DRUG; VASCULOTROPIN A; VASCULOTROPIN RECEPTOR 2;

AMINO ACID SUBSTITUTION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; AUTOCRINE EFFECT; CANCER CELL; CANCER MODEL; CHEMICAL MUTAGENESIS; CHIRALITY; COLORECTAL TUMOR; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG MEGADOSE; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; EPIMERIZATION; HUMAN; HUMAN CELL; HYBRID; IN VIVO STUDY; LOW DRUG DOSE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RECEPTOR DOWN REGULATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TUMOR XENOGRAFT;

EID: 80955122677     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200176m     Document Type: Article

References (29)

1. Baselga, J. Targeting tyrosine kinases in cancer: the second wave Science 2006, 312, 1175-1178 (Pubitemid 43801135)
2. Lurje, G.; Lenz, H.-J. EGFR signaling and drug discovery Oncology 2009, 77, 400-410
3. Chow, L. Q.; Eckhardt, S. G. Sunitinib: From rational design to clinical efficacy J. Clin. Oncol. 2007, 25, 884-96 (Pubitemid 350002890)
4. Kling, J. Bundling next-generation cancer therapies for synergy Nat. Biotechnol. 2006, 24, 871-872 (Pubitemid 44215364)
5. Martinelli, E.; Troiani, T.; Morgillo, F.; Rodolico, G.; Vitagliano, D.; Morelli, M. P.; Tuccillo, C.; Vecchione, L.; Capasso, A.; Orditura, M.; De Vita, F.; Eckhardt, S. G.; Santoro, M.; Berrino, L.; Cardiello, F. Synergistic antitumor activity of sorafenib in combination with epidermal growth factor receptor inhibitors in colorectal and lung cancer cells Clin. Cancer Res. 2010, 16, 4990-5001
6. Hurwitz, H.; Fehrenbacher, L.; Novotny, W.; Cartwright, T.; Hainsworth, J.; Heim, W.; Berlin, J.; Baron, A.; Griffing, S.; Holmgren, E.; Ferrara, N.; Fyfe, G.; Rogers, B.; Ross, R.; Kabbinavar, F. Bevacizumab plus irinotecan, fluorouracil, and leucovorin for metastatic colorectal cancer N. Engl. J. Med. 2004, 350, 2335-2342 (Pubitemid 38702844)
7. Koutras, A. K.; Starakis, I.; Kyriakopoulou, U.; Katsaounis, P.; Nikolakopoulos, A.; Kalofonos, H. P. Targeted therapy in colorectal cancer: Current status and future challenges Curr. Med. Chem. 2011, 18, 1599-1612
8. Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J.; Corbett, T. H. Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula J. Am. Chem. Soc. 2001, 123, 5418-5423 (Pubitemid 32888509)
9. Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J.; Corbett, T. H. New apratoxins of marine cyanobacterial origin from Guam and Palau Bioorg. Med. Chem. 2002, 10, 1973-1978 (Pubitemid 34286391)
10. Gutierrez, M.; Suyama, T. L.; Engene, N.; Wingerd, J. S.; Matainaho, T.; Gerwick, W. H. Apratoxin D, a potent cytotoxic cyclodepsipeptide from Papua New Guinea collections of the marine cyanobacteria Lyngbya majuscula and Lyngbya sordida J. Nat. Prod. 2008, 71, 1099-1103 (Pubitemid 352008918)
11. Matthew, S.; Schupp, P. J.; Luesch, H. Apratoxin E, a cytotoxic peptolide from a Guamanian collection of the marine cyanobacterium Lyngbya bouillonii J. Nat. Prod. 2008, 71, 1113-1116 (Pubitemid 352008922)
12. Tidgewell, K.; Engene, N.; Byrum, T.; Media, J.; Doi, T.; Valeriote, F. A.; Gerwick, W. H. Evolved diversification of a modular natural product pathway: Apratoxins F and G, two cytotoxic cyclic depsipeptides from a Palmyra collection of Lyngbya bouillonii ChemBioChem 2010, 11, 1458-1466
13. Liu, Y.; Law, B. K.; Luesch, H. Apratoxin A reversibly inhibits the secretory pathway by preventing cotranslational translocation Mol. Pharmacol. 2009, 76, 91-104
14. Pleiotropic mechanisms on HSP90 client proteins have been proposed for the apratoxins, although many of these observations may be rationalized by inhibition of the secretory pathway: Shen, S.; Zhang, P.; Lovchik, M. A.; Li, Y.; Tang, L.; Chen, Z.; Zeng, R.; Ma, D.; Yuan, J.; Yu, Q. Cyclodepsipeptide toxin promotes the degradation of Hsp90 client proteins through chaperone-mediated autophagy J. Cell. Biol. 2009, 185, 629-639
15. Ruan, W.-J.; Lai, M.-D. Autocrine stimulation in colorectal carcinoma (CRC): Positive autocrine loops in human colorectal carcinoma and applicable significance of blocking the loops Med. Oncol. 2004, 21, 1-7 (Pubitemid 38491324)
16. Chen, J.; Forsyth, C. J. Total synthesis of apratoxin A J. Am. Chem. Soc. 2003, 125, 8734-8735 (Pubitemid 36886205)
17. Ma, D.; Zou, B.; Cai, G.; Hu, X.; Liu, J. O. Total synthesis of the cyclodepsipeptide apratoxin A and its analogues and assessment of their biological activities Chem.-Eur. J. 2006, 12, 7615-7626 (Pubitemid 44569854)
18. Doi, T.; Numajiri, Y.; Takahashi, T.; Takagi, M.; Shin-ya, K. Solid-phase total synthesis of (-)-apratoxin A and its analogues and their biological evaluation Chem. Asian J. 2011, 6, 180-188
19. Doi, T.; Numajiri, Y.; Munakata, A.; Takahashi, T. Total synthesis of apratoxin A Org. Lett. 2006, 8, 531-534 (Pubitemid 43241703)
20. Numajiri, Y.; Takahashi, T.; Doi, T. Total synthesis of (-)-apratoxin A, 34-epimer, and its oxazoline analogue Chem. Asian J. 2009, 4, 111-125
21. Xu, Z.; Chen, Z.; Ye, T. Synthesis of polyketide segment of apratoxin A Tetrahedron: Asymmetry 2004, 15, 355-363
22. Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. Asymmetric synthesis using diisopropyl tartrate modified (E)- and (Z)-crotylboronates: Preparation of the chiral crotylboronates and reactions with achiral aldehydes J. Am. Chem. Soc. 1990, 112, 6339-6348
23. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. A rapid esterification by means of mixed anhydride and its application to large-ring lactonization Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993
24. Travis, B. R.; Narayan, R. S.; Borhan, B. Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: an organometallic ozonolysis J. Am. Chem. Soc. 2002, 124, 3824-3825 (Pubitemid 34310885)
25. You, S.-L.; Razavi, H.; Kelly, J. W. A biomimetic synthesis of thiazolines using hexaphenyloxodiphosphonium trifluoromethanesulfonate Angew. Chem., Int. Ed. 2003, 42, 83-85 (Pubitemid 36109504)
26. Carmeliet, P.; Jain, R. K. Angiogenesis in cancer and other diseases Nature 2000, 407, 249-257
27. Folkman, J. Angiogenesis in cancer, vascular, rheumatoid and other disease Nat. Med. 1995, 1, 27-31
28. Kerbel, R. S. Tumor angiogenesis: Past, present and the near future Carcinogenesis 2000, 21, 505-515 (Pubitemid 30137936)
29. Luesch, H.; Chanda, S. K.; Raya, R. M.; DeJesus, P. D.; Orth, A. P.; Walker, J. R.; Izpisúa Belmonte, J. C.; Schultz, P. G. A functional genomics approach to the mode of action of apratoxin A Nat. Chem. Biol. 2006, 2, 158-167 (Pubitemid 44323868)