Boromycin

Boromycin

File:Boromycin.png
Systematic (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-kO)-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
Clinical data
Legal status	US: ℞-only
Identifiers
CAS Number	34524-20-4 Y
ATC code	none
PubChem	CID: 6436027
ChemSpider	16735705 Y
UNII	49559OZO07 N
ChEBI	CHEBI:77880 N
Chemical data
Formula	C45H74BNO15
Molecular mass	879.878 g/mol
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 strain 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.