The protein synthesis inhibitors mycalamides A and E have limited susceptibility toward the drug efflux network

Journal of Biochemical and Molecular Toxicology

Volumn 26, Issue 3, 2012, Pages 94-100

  Venturi, Veronica ^a   Davies, Carolina ^a,b   Singh, A Jonathan ^a   Matthews, James H ^a   Bellows, David S ^a   Northcote, Peter T ^a   Keyzers, Robert A ^a   Teesdale Spittle, Paul H ^a  

^a VICTORIA UNIVERSITY OF WELLINGTON   (New Zealand)

^b INIQUI   (Argentina)

Author keywords

Efflux; Mycalamide; PDR; Resistance

Indexed keywords

ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; ERGOSTEROL; GLYCOPROTEIN P; MYCALAMIDE A; MYCALAMIDE E; UNCLASSIFIED DRUG; VERAPAMIL;

ANTIFUNGAL RESISTANCE; ANTIFUNGAL SUSCEPTIBILITY; ARTICLE; CELL DENSITY; CELL PROLIFERATION; CHEMOSENSITIVITY; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; DRUG TRANSPORT; FUNGUS GROWTH; GENE DELETION; HUMAN; HUMAN CELL; MEMBRANE STRUCTURE; NONHUMAN; PROTEIN EXPRESSION; PROTEIN SYNTHESIS INHIBITION; SACCHAROMYCES CEREVISIAE; STEROL SYNTHESIS; XENOBIOTIC METABOLISM;

ANIMALS; ANTIFUNGAL AGENTS; CELL LINE; CELL PROLIFERATION; GENE DELETION; HUMANS; MARINE TOXINS; MICROBIAL SENSITIVITY TESTS; PORIFERA; PROTEIN SYNTHESIS INHIBITORS; PYRANS; SACCHAROMYCES CEREVISIAE;

SACCHAROMYCES CEREVISIAE;

EID: 84858748574     PISSN: 10956670     EISSN: 10990461     Source Type: Journal    
DOI: 10.1002/jbt.20414     Document Type: Article

References (34)

1. Perry NB, Blunt JW, Munro MHG, Pannell LK. Mycalamide A. An antiviral compound from a New Zealand sponge of the genus Mycale. J Am Chem Soc 1988;110:4850-4851.
2. Burres NS, Clement JJ. Antitumor activity and mechanism of action of the novel marine natural products mycalamide-A and -B and onnamide. Cancer Res 1989;49:2935-2940.
3. Richter A, Kocienski P, Raubo P, Davies DE. The in vitro biological activities of synthetic 18-O-methyl mycalamide B, 10-epi-18-O-methyl mycalamide B and pederin. Anticancer Drug Des 1997;12:217-227.
4. Lee K-H, Nishimura S, Matsunaga S, Fusetani N, Horinouchi S, Yoshida M. Inhibition of protein synthesis and activation of stress-activated protein kinases by onnamide A and theopederin B, antitumor marine natural products. Cancer Sci 2005;96:357-364.
5. Ogawara H, Higashi K, Uchino K, Perry NB. Change of ras-transformed NRK-cells back to normal morphology by mycalamides A and B, antitumor agents from a marine sponge. Chem Pharm Bull 1991;39:2152-2154.
6. Hood K, West L, Northcote P, Berridge M, Miller J. Induction of apoptosis by the marine sponge (Mycale) metabolites, mycalamide A and pateamine. Apoptosis 2001;6:207-219.
7. Galvin F, Freeman GJ, Razi-Wolf Z, Benacerraf B, Nadler L, Reiser H. Effects of cyclosporin A, FK 506, and mycalamide A on the activation of murine CD4 + T cells by the murine B7 antigen. Eur J Immunol 1993;23:283-286.
8. Vuong D, Capon RJ, Lacey E, Gill JH, Heiland K, Friedel T. Onnamide F: a new nematocide from a southern Australian marine sponge, Trachycladus laevispirulifer. J Nat Prod 2001;64:640-642.
9. Tsukamoto S, Matsunaga S, Fusetani N, Toh-e A. Theopederins F-J. Five new antifungal and cytotoxic metabolites from the marine sponge, Theonella swinhoei. Tetrahedron 1999;55:13697-13702.
10. Gurel G, Blaha G, Steitz TA, Moore PB. Structures of triacetyloleandomycin and mycalamide A bind to the large ribosomal subunit of Haloarcula marismortui. Antimicrob Agents Chemother 2009;53:5010-5014.
11. Sohn J-H, Waizumi N, Zhong HM, Rawal VH. Total synthesis of mycalamide A. J Am Chem Soc 2005;127:7290-7291.
12. Kagawa N, Ihara M, Toyota M. Convergent total synthesis of (+)-mycalamide A. J Org Chem 2006;71:6796-6805.
13. Jewett JC, Rawal VH. Total synthesis of pederin. Angew Chem, Int Ed 2007;46:6502-6504.
14. Green ME, Rech JC, Floreancig PE. Total synthesis of theopederin D. Angew Chem, Int Ed 2008;47:7317-7320.
15. Huang X, Shao N, Huryk R, Palani A, Aslanian R, Seidel-Dugan C. The discovery of potent antitumor agent C11-deoxypsymberin/irciniastatin A: total synthesis and biology of advanced psymberin analogs. Org Lett 2009;11:867-870.
16. Jiang X, Williams N, De Brabander JK. Synthesis of psymberin analogues: probing a functional correlation with the pederin/mycalamide family of natural products. Org Lett 2007;9:227-230.
17. Piel J. Bacterial symbionts: prospects for the sustainable production of invertebrate-derived pharmaceuticals. Curr Med Chem 2006;13:39-50.
18. Piel J, Hui D, Wen G, Butzke D, Platzer M, Fusetani N, Matsunaga S. Antitumor polyketide biosynthesis by an uncultivated bacterial symbiont of the marine sponge Theonella swinhoei. Proc Natl Acad Sci U S A 2004;101:16222-16227.
19. Zimmermann K, Engeser M, Blunt JW, Munro MHG, Piel J. Pederin-type pathways of uncultivated bacterial symbionts: analysis of O-methyltransferases and generation of a biosynthetic hybrid. J Am Chem Soc 2009;131:2780-2781.
20. Sarkadi B, Homolya L, Szakács G, Váradi A. Human multidrug resistance ABCB and ABCG transporters: participation in a chemoimmunity defense system. Physiol Rev 2006;86:1179-1236.
21. Schinkel AH, Jonker JW. Mammalian drug efflux transporters of the ATP binding cassette (ABC) family: an overview. Adv Drug Delivery Rev 2003;55:3-29.
22. Alenquer M, Tenreiro S, Sá-Correia I. Adaptive response to the antimalarial drug artesunate in yeast involves Pdr1p/Pdr3p-mediated transcriptional activation of the resistance determinants TPO1 and PDR5. FEMS Yeast Res 2006;6:1130-1139.
23. Shahi P, Moye-Rowley WS. Coordinate control of lipid composition and drug transport activities is required for normal multidrug resistance in fungi. Biochim Biophys Acta Proteins Proteomics 2009;1794:852-859.
24. Stansfield I, Stark MJ. Yeast genetics and strain construction. In: Yeast gene analysis, 2nd edition; Methods in Microbiology, Vol 36; New York: Academic Press, 2007. pp 23-43.
25. Thompson AM, Blunt JW, Munro MHG, Perry NB. Chemistry of the mycalamides, antiviral and antitumour compounds from a marine sponge, Part 5: Acid-catalysed hydrolysis and acetal exchange, double bond additions and oxidation reactions. J Chem Soc, Perkin Trans 1 1995;1233-1244.
26. Banerjee D, Lelandais G, Shukla S, Mukhopadhyay G, Jacq C, Devaux F, Prasad R. Responses of pathogenic and nonpathogenic yeast species to steroids reveal the functioning and evolution of multidrug resistance transcriptional networks. Eukaryotic Cell 2008;7:68-77.
27. DeRisi J, van den Hazel B, Marc P, Balzi E, Brown P, Jacq C, Goffeau A. Genome microarray analysis of transcriptional activation in multidrug resistance yeast mutants. FEBS Lett 2000;470:156-160.
28. Fardeau V, Lelandais G, Oldfield A, Salin H, Lemoine S, Garcia M, Tanty V, Le Crom S, Jacq C, Devaux F. The central role of PDR1 in the foundation of yeast drug resistance. J Biol Chem 2007;282:5063-5074.
29. Ferreira-Pereira A, Marco S, Decottignies A, Nader J, Goffeau A, Rigaud J-L. Three-dimensional reconstruction of the Saccharomyces cerevisiae multidrug resistance protein Pdr5p. J Biol Chem 2003;278:11995-11999.
30. Decottignies A, Goffeau A. Complete inventory of the yeast ABC proteins. Nat Genet 1997;15:137-145.
31. Stepanov A, Nitiss KC, Neale G, Nitiss JL. Enhancing drug accumulation in Saccharomyces cerevisiae by repression of pleiotropic drug resistance genes with chimeric transcription repressors. Mol Pharmacol 2008;74:423-431.
32. Kolaczkowski M, Michel van der R, Cybularz-Kolaczkowska A, Soumillion J-P, Konings WN, André G. Anticancer drugs, ionophoric peptides, and steroids as substrates of the yeast multidrug transporter Pdr5p. J Biol Chem 1996;271:31543-31548.
33. Hallstrom T, Katzmann D, Torres R, Sharp W, Moye-Rowley W. Regulation of transcription factor Pdr1p function by an Hsp70 protein in Saccharomyces cerevisiae. Mol Cell Biol 1998;18:1147-1155.
34. Gaitanos TN, Buey RM, Díaz JF, Northcote PT, Teesdale-Spittle P, Andreu JM, Miller JH. Peloruside A does not bind to the taxoid site on β-tubulin and retains its activity in multidrug-resistant cell lines. Cancer Res 2004;64:5063-5067.