Boromycin, an Anti-HIV Antibiotic

Abstract

The polyether-macrolide antibiotic, boromycin, was isolated as a potent anti-human immunodeficiency virus (HIV) antibiotic from a fermentation broth of Streptomyces sp. A-3376. Boromycin was found to strongly inhibit the replication of the clinically isolated HIV-1 strain as well as the cultured strain in in vitro laboratory experiments. The mechanism for the anti-HIV activity of boromycin is suggested to involve blocking the later stage of HIV infection, and probably the maturity step for replication of the HIV molecule.

Biologically active compounds of semi-metals

“…It is also active against protozoa of the genera plasmodiae and babesiae (Prelog et al, 1973) and has been used for the treatment and prevention of coccidiosis in susceptible poultry (Miller and Burg, 1975). Boromycin was found to strongly inhibit the replication of HIV-1 (Kohno et al, 1996). It also inhibits the synthesis of protein, RNA and DNA in whole cells of Bacillus subtilis (Pache and Zahner, 1969).…”

Synthesis of novel dehydroacetic acid N -aroylhydrazone-derived boron heterocycles

“…The signals at lowest field, in the ranges 170.3e171.0 and 171.2e172.5 ppm, are assigned to C-4 of the pyrone ring and the carbonyl carbon of the acetoxy group, respectively. In the cases of boron heterocycles 6c (R¼p-ClC 6 H 4 ) and 6d (R¼p-O 2 NC 6 H 4 ) only, where both 1 H and 13 C NMR spectra were obtained in DMSO-d 6 , there was evidence for the existence of two stereoisomers, with respect to the tetracoordinated boron atom. Specifically, in the 13 C NMR spectra there were two signals for each of the two types of methyl, two ester carbonyl carbon signals, and two peaks for C-4 of the pyrone ring.…”

“…IR spectra were recorded on an FTIR Nicolet 200 spectrometer. 1 H (400 MHz) and 13 C (100 MHz) NMR spectra were recorded on a Bruker Avance 400 instrument and the chemical shifts are reported in d (ppm) values relative to either CDCl 3 , (d¼7.30 and 77.0 ppm for 1 H and 13 C NMR, respectively, for CDCl 3 ) or DMSO-d 6 (d¼2.50 and 39.5 ppm for 1 H and 13 C NMR, respectively, for DMSO-d 6 ). Coupling constants are reported in hertz (Hz).…”

“…1) a polyether macrolide antibiotic active against Gram-positive bacteria 5 that was shown to also have anti-HIV activity. 6 Another interesting boroncontaining natural product is a hydrated boric acid complex with a tetrahydroxy-dihydrofuran, known as AI-2, which is a bacterial autoinducer involved in quorum sensing. 7 Trivalent boron compounds have an empty p-orbital, which makes them strong electrophiles and Lewis acids.…”

Boron Functions in Plants and Animals: Recent Advances in Boron Research and Open Questions

“…The boron-containing antibiotic boromycin from Streptomyces sp. strain A-3376 was recently found to be a potent anti-human immunodeficiency virus (HIV) antibiotic (Kohno et al 1996), acting by (in part) still unknown mechanisms. Generally, boron-containing antibiotics such as boromycin, tartrolon B and aplasmomycin are borodiesters and act as ionophores.…”