Boromycin

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.

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
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC45H74BNO15
Molar mass879.89 g·mol−1
3D model (JSmol)
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)

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.
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