A boron-containing macrolide antibiotic
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Boromycin

Item No. 28245

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(T-4)-[(1R)-1-[(1S,2R,5S,6R,8R,12R,14S,17R,18S,19R,22S,24Z,28S,30S,33R)-1,2,18,19-tetra(hydroxy-κO)-12,28-dihydroxy-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]ethyl D-valinato(4-)]-borate(1-), monohydrogen
CAS Number
34524-20-4
Synonyms
  • NSC 121380
Molecular Formula
C45H73BNO15 • H
Formula Weight
879.9
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleEthanol: solubleMethanol: soluble
SMILES
C[C@H](CC[C@@H](C(C)([C@H](CC/C=C/C[C@@H]([C@@H](C)OC([C@H](N)C(C)C)=O)O1)O)C)O2)[C@]32[O-][B+3]4([O-][C@]5(O[C@H](C6(C)C)CC[C@H]5C)[C@H](C1=O)[O-]4)[O-][C@H]3C(O[C@H]7C[C@@H](CCC[C@H]6O)O[C@@H]7C)=O.[H+]
InChi Code
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+/m1/s1
InChi Key
OOBFYEMEQCZLJL-QAZYKMQESA-O
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Boromycin is a boron-containing macrolide antibiotic that has been found in Streptomyces.1 Boromycin inhibits growth of B. subtilis (MIC = 0.05 µg/ml) and induces efflux of potassium ions from B. subtilis without affecting Na+/K+-ATPase activity.2 It decreases the synthesis of protein, RNA, and DNA in B. subtilis when used at a concentration of 0.05 µg/ml. It inhibits the growth of B. halodurans (MIC = 10 ng/ml) and inhibits the futalosine pathway of menaquinone synthesis in B. halodurans.3 Boromycin (3.4 nM) reverses bleomycin-induced cell cycle arrest at the G2 phase in Jurkat cells.4 It inhibits replication of the HIV-1 strains LAV-1 and RF and the HIV-2 strain LAV-2 in MT-4 cells (IC50s = 0.008, 0.11, and 0.007 µM, respectively).1 It also inhibits replication of a clinical isolate of HIV-1, strain KK-1, in MT-4 cells and peripheral blood mononuclear cells (PBMCs; IC50s = 0.14 and <0.1 µM, respectively).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kohno, J., Kawahata, T., Otake, T., et al. Boromycin, an anti-HIV antibiotic. Biosci. Biotech. Biochem. 60(6), 1036-1037 (1996).

    2. Pache, W., and Zähner, H. Metabolic products of microorganisms. 77. Studies on the mechanism of action of boromycin. Arch. Mikrobiol. 67(2), 156-165 (1969).

    3. Shimizu, Y., Ogasawara, Y., Matsumoto, A., et al. Aplasmomycin and boromycin are specific inhibitors of the futalosine pathway. J. Antibiot. (Tokyo) 71(11), 968-970 (2018).

    4. Arai, M., Koizumi, Y., Sato, H., et al. Boromycin abrogates bleomycin-induced G2 checkpoint. J. Antibiot. (Tokyo) 57(10), 662-668 (2004).