Antimicrobial activities of 3-amino- and polyaminosterol analogues of squalamine and trodusquemine

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 23, Issue 6, 2008, Pages 860-865

  Salmi, Chanaz ^a   Loncle, Celine ^a   Vidal, Nicolas ^a   Laget, Michèle ^a   Letourneux, Yves ^a   Brunel, Jean Michel ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Aminosterol derivatives; Antibacterial activity; Antifungal activity; Squalamine; Trodusquemine

Indexed keywords

3 AMINOSTEROL DERIVATIVE; ANTIINFECTIVE AGENT; ECONAZOLE; POLYAMINOSTEROL DERIVATIVE; SQUALAMINE; STEROL DERIVATIVE; STREPTOMYCIN; TRODUSQUEMINE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; YEAST;

AMINES; ANTI-BACTERIAL AGENTS; CHOLESTANES; CHOLESTANOLS; MICROBIAL VIABILITY; MOLECULAR STRUCTURE; SPERMINE; STEROLS; STRUCTURE-ACTIVITY RELATIONSHIP;

NEGIBACTERIA; POSIBACTERIA;

EID: 56449085001     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360701809910     Document Type: Article

References (25)

1. Boman, HG (1991) Antibacterial peptides: Key components needed in immunity. Cell, 65, pp. 205-207.
2. Cho, J. and Kim, Y. (2002) Sharks: A Potential Source of Antiangiogenic Factors and Tumor Treatments. Marine Biotechnol, 4, pp. 521-525.
3. Stone, R. (1993) Deja vu guides the way to new antimicrobial steroid. Science, 259, p. 1125.
4. Zasloff M. (1992) Curr Opin Immunol, 4, pp. 3-7.
5. Zasloff, M. (1994) Antibacterial molecules from frogs, sharks and man. Phylogenet Perspect Immun Insect Host Def, pp. 31-41.
6. Wehrli, SL, Moore, KS, Roder, H., Durell, S. and Zasloff, M. (1993) Structure of the novel steroidal antibiotic squalamine determined by two-dimensional NMR spectroscopy. Steroids, 58, pp. 370-378.
7. Savage, PB (2002) Cationic steroid antibiotics. Curr Med Chem-Anti-Infective Agents, 1, pp. 293-304.
8. Savage, PB (2002) Design, synthesis and characterization of cationic peptide and steroid antibiotics. Eur J Org Chem, pp. 759-768.
9. Moore, KS, Wehrli, S., Roder, H., Rogers, M., Forrest Jr, JN, McCrimmon, D. and Zasloff, M. (1993) Squalamine: An aminosterol antibiotic from the shark. Proc Natl Acad Sci USA, 90, pp. 1354-1358.
10. Rao, MN, Shinnar, AE, Noecker, LA, Chao, TL, Feibush, B., Snyder, B., Sharkansky, I., Sarkahian, A., Zhang, X., Jones, SR, Kinney, WA and Zasloff, M. (2000) Aminosterols from the dogfish shark Squalus acanthias. J Nat Prod, 63, pp. 631-635.
11. Brunel, JM and Letourneux, Y. (2003) Recent advances in the synthesis of spermine and spermidine analogs of the shark aminosterol squalamine. Eur J Org Chem, pp. 3897-3907.
12. Brunel, JM, Salmi, C., Loncle, C., Vidal, N. and Letourneux, Y. (2005) Squalamine: A polyvalent drug of the future. Curr Cancer Drug Targets, 5, pp. 267-272.
13. Hamana, K. and Matsuzaki, S. (1992) Polyamines as a chemotaxonomic marker in bacterial systematics. Crit Rev Microbiol, 18, pp. 261-283.
14. Wallace, HM (1998) Polyamines: Specific metabolic regulators or multifunctional polycations?. Biochem Soc Trans, 26, pp. 569-571.
15. Wallace, HM (2000) The physiological role of the polyamines. Eur J Clin Inv, 30, pp. 1-3.
16. Wallace, HM (2003) Polyamines and their role in human disease - an introduction. Biochem Soc Trans, 31, pp. 354-355.
17. Saunders, FR and Wallace, HM (2007) Polyamine metabolism and cancer prevention. Biochem Soc Trans, 35, pp. 364-368.
18. Yasuda, K., Ohmizo, C. and Katsu, T. (2004) Mode of action of novel polyamines increasing the permeability of bacterial outer membrane. Int J of Antimicrob Agents, 24, pp. 67-71.
19. Kim, HS, Choi, BS, Kwon, KC, Lee, SO, Kwak, HJ and Lee, CH (2000) Synthesis and antimicrobial activity of squalamine analogue. Bioorg Med Chem, 8, pp. 2059-2065.
20. Kikuchi, K., Bernard, EM, Sadownik, A., Regen, SL and Armstrong, D. (1997) Antimicrobial activities of squalamine mimics. Antimicrob Agents Chemother, 41, pp. 1433-1438.
21. Jones, SR, Kinney, WA, Zhang, X., Jones, LM and Selinsky, BS (1996) The synthesis and characterization of analogs of the antimicrobial compound squalamine: 6β-hydroxy-3-aminosterols synthesized from hyodeoxycholic acid. Steroids, 61, pp. 565-571.
22. Sadownik, A., Deng, G., Janout, V., Regen, SL, Bernard, EM, Kikuchi, K. and Armstrong, D. (1995) Rapid Construction of a Squalamine Mimic. J Am Chem Soc, 117, pp. 6138-6139.
23. Khabnadideh, S., Tan, CL, Croft, SL, Kendrick, H., Yardley, V. and Gilbert, IH (2000) Squalamine analogs as potential anti-trypanosomal and anti-leishmanial compounds. Bioorg Med Chem Lett, 10, pp. 1237-1239.
24. Salmi, C., Letourneux, Y. and Brunel, JM (2006) Efficient synthesis of various secondary amines through a titanium(IV) isopropoxide-mediated reductive amination of ketones. Lett Org Chem, 3, pp. 396-401.
25. Salmi, C., Letourneux, Y. and Brunel, JM (2006) Efficient diastereoselective titanium(IV) reductive amination of ketones. Lett Org Chem, 3, pp. 384-389.