Effects of ulapualide A and synthetic macrolide analogues on actin dynamics and gene regulation

Cellular and Molecular Life Sciences

Volumn 64, Issue 4, 2007, Pages 487-497

  Vincent, E ^a,b   Saxton, J ^a   Baker Glenn, C ^a   Moal, I ^a   Hirst, J D ^a   Pattenden, G ^a   Shaw, P E ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Actin cytoskeleton; Immediate early genes; Serum response factor; Toxins; Transcription

Indexed keywords

ACTIN CAPPING PROTEIN; ALIPHATIC COMPOUND; MACROLIDE; SERUM RESPONSE FACTOR; ULAPUALIDE A; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL ADHESION; CONTROLLED STUDY; CYTOSKELETON; DEPOLYMERIZATION; DIASTEREOISOMER; DRUG ACTIVITY; DRUG MECHANISM; DRUG PROTEIN BINDING; EMBRYO; FEMALE; GENE EXPRESSION; GENETIC REGULATION; HUMAN; HUMAN CELL; IN VITRO STUDY; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ACTINS; ANIMALS; CELL ADHESION; CYTOSKELETON; GENE EXPRESSION REGULATION; HELA CELLS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HUMANS; MACROLIDES; MICE; MODELS, MOLECULAR; NIH 3T3 CELLS; OXAZOLES; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33847244843     PISSN: 1420682X     EISSN: 15691632     Source Type: Journal    
DOI: 10.1007/s00018-007-6427-1     Document Type: Article

References (29)

1. Spector, I., Braet, F., Shochet, N. R. and Bubb, M. R. (1999) New anti-actin drugs in the study of the organization and function of the actin cytoskeleton. Microsc. Res. Tech. 41, 18-37.
2. Yeung, K. S. and Paterson, I. (2002) Actin-binding marine macrolides: total synthesis and biological importance. Angew. Chem. Int. Ed. Engl. 41, 4632-4653.
3. Cen, B., Selvaraj, A. and Prywes, R. (2004) Myocardin/MKL family of SRF coactivators: Key regulators of immediate early and muscle specific gene expression. J. Cell. Biochem. 93, 74-82.
4. dos Remedios, C. G., Chhabra, D., Kekic, M., Dedova, I. V., Tsubakhara, M., Berry, D. A. and Nosworth, N. J. (2003) Actin binding proteins: regulation of cytoskeletal microfilaments. Physiol. Rev. 83, 433-473.
5. Giganti, A. and Friederich, E. (2003) The actin cytoskeleton as a therapeutic target: state of the art and future directions. Prog. Cell Cycle Res. 5, 511-525.
6. Cen, B., Selvaraj, A., Burgess, R. C., Hitzler, J. K., Ma, Z., Morris, S. W. and Prywes, R. (2003) Megakaryoblastic leukemia 1, a potent transcriptional coactivator for serum response factor (SRF), is required for serum induction of SRF target genes. Mol. Cell. Biol. 23, 6597-6608.
7. Wang, D. Z., Li, S., Hockemeyer, D., Sutherland, L., Wang, Z., Schratt, G., Richardson, J. A., Nordheim, A. and Olson, E. N. (2002) Potentiation of serum response factor activity by a family of myocardin-related transcription factors. Proc. Natl. Acad. Sci. USA 99, 14855-14860.
8. Miralles, F., Posern, G., Zaromytidou, A. and Treisman, R. (2003) Actin dynamics control SRF activity by regulation of its coactivator MAL. Cell 113, 329-342.
9. Morton, W. M., Ayscough, K. R. and McLaughlin, P. J. (2000) Latrunculin alters the actin-monomer subunit interface to prevent polymerization. Nat. Cell Biol. 2, 376-378.
10. Bubb, M. R., Senderowicz, A. M., Sausville, E.A., Duncan, K. L. and Korn, E. D. (1994) Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-actin. J. Biol. Chem. 269, 14869-14871.
11. Bubb, M. R., Spector, I., Bershadsky, A. D. and Korn, E. D. (1995) Swinholide A is a microfilament disrupting marine toxin that stabilizes actin dimers and severs actin filaments. J. Biol. Chem. 270, 3463-3466.
12. Goddette, D.W. and Frieden, C. (1986) Actin polymerization. Themechanism of action of cytochalasin D. J. Biol. Chem. 261, 15974-15980.
13. Sotiropoulos, A., Gineitis, D., Copeland, J. and Treisman, R. (1999) Signal-regulated activation of serum response factor is mediated by changes in actin dynamics. Cell 98, 159-169.
14. Klenchin, V. A., Allingham, J. S., King, R., Tanaka, J., Marriott, G. and Rayment, I. (2003) Trisoxazole macrolide toxins mimic the binding of actin-capping proteins to actin. Nat. Struct. Biol. 10, 1058-1063.
15. Allingham, J. S., Tanaka, J., Marriott, G. and Rayment, I. (2004) Absolute stereochemistry of ulapualide A. Org. Lett. 6, 597-599.
16. Tanaka, J., Yan, Y., Choi, J., Bai, J., Klenchin, V. A., Rayment, I. and Marriott, G. (2003) Biomolecular mimicry in the actin cytoskeleton: Mechanisms underlying the cytotoxicity of kabiramide C and related macrolides. Proc. Natl. Acad. Sci. USA 100, 13851-13856.
17. Chattopadhyay, S. K. and Pattenden, G. (1998) Total synthesis of ulapualide A, a novel trisoxazole containing macrolide from the marine nudibranch Hexabranchus sanguineus. Tetrahedron Lett. 39, 6095-6098.
18. Chattopadhyay, S. K. and Pattenden, G. (2000) A total synthesis of the unique tris-oxazole macrolide ulapualide A produced by the marine nudibranch Hexabranchus sanguineus. J Chem. Soc. Perkin Trans 1, 2429-2454.
19. Frost, J. A., Steen, H., Shapiro, P., Lewis, T., Ahn, N., Shaw, P. E. and Cobb, M. H. (1997) Cross-cascade activation of ERKs and ternary complex factors by Rho family proteins. EMBO J, 16, 6426-6438.
20. Boussif, O., Lezoualc'h, F., Zanta, M. A., Mergny, M. D., Scherman, D., Demeneix, B. and Behr, J. P. (1995) A versatile vector for gene and oligonucleotide transfer into cells in culture and in vivo: polyethylenimine. Proc. Natl. Acad. Sci. USA 92, 7297-7301.
21. Pope, B. and Weeds,A.G. (1986) Binding of pig plasma gelsolin to F-actin and partial fractionation into calcium-dependent and calcium-independent forms. Eur. J. Biochem. 161, 85-93.
22. Morris, G.M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R.K. and Olson, A. J. (1998) Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function. J. Comput. Chem. 19, 1639-1662.
23. Hill, C. S., Wynne, J. and Treisman, R. (1995) The Rho family GTPasses RhoA, Rac1 and CDC42Hs regulate transcriptional activation by SRF. Cell 81, 1159-1170.
24. Shaw, P. E. and Saxton, J. (2003) Ternary complex factors: Prime nuclear targets for mitogen-activated protein kinases. Int. J. Biochem. Cell Biol. 35, 1210-1226.
25. Wang,D. Z. and Olson, E. N. (2004) Control of smooth muscle development by the myocardin family of transcriptional coactivators. Curr. Opin. Genet. Dev. 14, 558-566.
26. Kigoshi, H., Suenaga, K., Takagi, M., Akao, A., Kanematsu, K., Kamei, N., Okugawa, Y. and Yamada, K. (2002) Cytotoxicity and actin-depolymerizing activity of aplyronine A, a potent antitumor macrolide of marine origin, and its analogs. Tetrahedron 58, 1075-1102.
27. Petchprayoon, C., Suwanborirux, K., Miller, R., Sakata, T. and Marriott, G. (2005) Synthesis and characterization of the 7-(4-aminomethyl-1H-1,2,3- triazol-1-yl) analogue of kabiramide C. J. Nat. Prod. 68, 157-161.
28. Posern, G., Miralles, F., Guettler, S. and Treisman, R. (2004) Mutant actins that stabilise F-actin use distinct mechanisms to activate the SRF coactivator MAL. EMBO J. 23, 3973-3983.
29. Klenchin, V. A., King, R., Tanaka, J., Marriott, G. and Rayment, I. (2005) Structural basis of swinholide A binding to actin. Chem. Biol. 12, 287-291.