Boromycin

Boromycin

Clinical data
ATC code	none
Identifiers
IUPAC name [1-{(1R)-1-[(1R,2R,5S,6R,8R,12R,14S,17R,18R,22S,24Z,28S,30S,33R)-12,28-Dihydroxy-1,2,18,19-tetra(hydroxy-κO)-6,13,13,17,29,29,33-heptamethyl-3,20-dioxo-4,7,21,34,35-pentaoxatetracyclo[28.3.1.15,8.114,18]hexatriacont-24-en-22-yl]ethoxy}-3-methyl-1-oxo-2-butanaminiumato(4-)]boron
CAS Number	34524-20-4 Y
PubChem CID	6436027
ChemSpider	16735705 Y
UNII	49559OZO07
ChEBI	CHEBI:77880 N
CompTox Dashboard (EPA)	DTXSID10896996
Chemical and physical data
Formula	C45H74BNO15
Molar mass	879.89 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)C([NH3+])C(=O)O[C@H](C)[C@H]7OC(=O)C4O[B-]25O[C@@H](C(=O)O[C@H]1C[C@H](O[C@@H]1C)CCC[C@@H](O)C(C)(C)[C@@H]3CC[C@@H](C)[C@@]4(O2)O3)[C@]6(O5)O[C@@H](CC[C@H]6C)C(C)(C)[C@@H](O)CC\C=C/C7
InChI InChI=1S/C45H73BNO15/c1-24(2)36(47)39(50)54-27(5)30-16-12-11-13-17-32(48)42(7,8)34-21-19-26(4)45(57-34)38-41(52)56-31-23-29(53-28(31)6)15-14-18-33(49)43(9,10)35-22-20-25(3)44(58-35)37(40(51)55-30)59-46(60-38,61-44)62-45/h11-12,24-38,48-49H,13-23,47H2,1-10H3/q-1/p+1/b12-11-/t25-,26-,27-,28-,29-,30+,31+,32+,33-,34+,35+,36?,37?,38+,44+,45+,46?/m1/s1 Y Key:OOBFYEMEQCZLJL-WIHWYPJVSA-O Y
NY (what is this?)  (verify)

Boromycin is a bacteriocidal polyether-macrolide antibiotic. It was initially isolated from the Streptomyces antibioticus, and is notable for being the first natural product found to contain the element boron. It is effective against most Gram-positive bacteria, but is ineffective against Gram-negative bacteria. Boromycin kills bacteria by negatively affecting the cytoplasmic membrane, resulting in the loss of potassium ions from the cell.

Anti-HIV activity

Recent studies have suggested that boromycin has potent anti-HIV activity. It was found to strongly inhibit the replication of the clinically isolated HIV-1 strain as well as the cultured strain in vitro. The mechanism of action for the anti-HIV activity of boromycin is suggested to involve interfering with the later stage of HIV infection, and possibly the maturation step for the replication of HIV.

References

• Kohno J, Kawahata T, Otake T, Morimoto M, Mori H, Ueba N, Nishio M, Kinumaki A, Komatsubara S, Kawashima K (1996). "Boromycin, an anti-HIV antibiotic". Biosci Biotechnol Biochem. 60 (6): 1036–7. doi:10.1271/bbb.60.1036. PMID 8695905.
• Tom S. S. Chen; Ching-jer Chang & Heinz G. Floss (1981). "On the Biosynthesis of Boromycin". Journal of Organic Chemistry. 46 (13): 2661–2665. doi:10.1021/jo00326a010.
• R. Hütter; W. Keller-Schien; F. Knüsel; V. Prelog; G. C. Rodgers Jr.; P. Suter; G. Vogel; W. Voser; H. Zähner (1967). "Stoffwechselprodukte von Mikroorganismen. 57. Mitteilung. Boromycin". Helv. Chim. Acta. 50 (6): 1533–1539. doi:10.1002/hlca.19670500612. PMID 6081908.
• J. D. Dunitz; D. M. Hawley; D. Miklo; D. N. J. White; Yu. Berlin; R. Marui; V. Prelog (1971). "Structure of boromycin". Helv. Chim. Acta. 54 (6): 1709–1713. doi:10.1002/hlca.19710540624. PMID 5131791.