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MedKoo Cat#: 574126 | Name: Boromycin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Boromycin is a boron-containing macrolide antibiotic that inhibits growth of B. subtilis and induces efflux of potassium ions from B. subtilis without affecting Na+/K+-ATPase activity. It decreases the synthesis of protein, RNA, and DNA in B. subtilis, inhibits the growth of B. halodurans, and inhibits the futalosine pathway of menaquinone synthesis in B. halodurans. Boromycin reverses bleomycin-induced cell cycle arrest at the G2 phase in Jurkat cells. It inhibits replication of the HIV-1 strains LAV-1 and RF and the HIV-2 strain LAV-2 in MT-4 cells. It also inhibits replication of a clinical isolate of HIV-1, strain KK-1, in MT-4 cells and peripheral blood mononuclear cells.

Chemical Structure

Boromycin
Boromycin
CAS#34524-20-4

Theoretical Analysis

MedKoo Cat#: 574126

Name: Boromycin

CAS#: 34524-20-4

Chemical Formula: C45H74BNO15

Exact Mass: 879.5152

Molecular Weight: 879.89

Elemental Analysis: C, 61.43; H, 8.48; B, 1.23; N, 1.59; O, 27.27

Price and Availability

Size Price Availability Quantity
1mg USD 650.00 2 Weeks
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Related CAS #
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Synonym
Boromycin; Antibiotic A 28829; Antibiotic A28829; NSC 121380; NSC121380; NSC-121380
IUPAC/Chemical 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
InChi Key
OOBFYEMEQCZLJL-BABIDTEZSA-O
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?,46?/m1/s1
SMILES Code
C[C@H]1[C@]2(O[C@@](C(C)([C@H](O)CCC[C@@]3([H])O[C@H](C)[C@](OC4=O)([H])C3)C)([H])CC1)O[B-]5(OC6([C@H](C)CC7)C4O5)OC2C(O[C@]([C@@H](C)OC([C@@H](C(C)C)[NH3+])=O)([H])C/C=C/CC[C@H](O)C(C)(C)[C@@]7([H])O6)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 879.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Abenoja J, Cotto-Rosario A, O'Connor R. Boromycin Has Potent Anti-Toxoplasma and Anti-Cryptosporidium Activity. Antimicrob Agents Chemother. 2021 Mar 18;65(4):e01278-20. doi: 10.1128/AAC.01278-20. PMID: 33468470; PMCID: PMC8097477. 2: de Carvalho LP, Groeger-Otero S, Kreidenweiss A, Kremsner PG, Mordmüller B, Held J. Boromycin has Rapid-Onset Antibiotic Activity Against Asexual and Sexual Blood Stages of Plasmodium falciparum. Front Cell Infect Microbiol. 2022 Jan 14;11:802294. doi: 10.3389/fcimb.2021.802294. PMID: 35096650; PMCID: PMC8795978. 3: Moreira W, Aziz DB, Dick T. Boromycin Kills Mycobacterial Persisters without Detectable Resistance. Front Microbiol. 2016 Feb 22;7:199. doi: 10.3389/fmicb.2016.00199. PMID: 26941723; PMCID: PMC4761863. 4: Kohno J, Kawahata T, Otake T, Morimoto M, Mori H, Ueba N, Nishio M, Kinumaki A, Komatsubara S, Kawashima K. Boromycin, an anti-HIV antibiotic. Biosci Biotechnol Biochem. 1996 Jun;60(6):1036-7. doi: 10.1271/bbb.60.1036. PMID: 8695905. 5: Dunitz JD, Hawley DM, Miklos D, White DN, Berlin Y, Marusić R, Prelog V. Structure of boromycin. Helv Chim Acta. 1971;54(6):1709-13. doi: 10.1002/hlca.19710540624. PMID: 5131791. 6: Arai M, Koizumi Y, Sato H, Kawabe T, Suganuma M, Kobayashi H, Tomoda H, Omura S. Boromycin abrogates bleomycin-induced G2 checkpoint. J Antibiot (Tokyo). 2004 Oct;57(10):662-8. doi: 10.7164/antibiotics.57.662. PMID: 15638327. 7: Shimizu Y, Ogasawara Y, Matsumoto A, Dairi T. Aplasmomycin and boromycin are specific inhibitors of the futalosine pathway. J Antibiot (Tokyo). 2018 Nov;71(11):968-970. doi: 10.1038/s41429-018-0087-2. Epub 2018 Aug 8. PMID: 30089869. 8: Maier V, Ranc V, Svidrnoch M, Petr J, Sevčík J, Tesařová E, Armstrong DW. Study on the use of boromycin as a chiral selector in capillary electrophoresis. J Chromatogr A. 2012 May 11;1237:128-32. doi: 10.1016/j.chroma.2012.02.073. Epub 2012 Mar 6. PMID: 22475183. 9: Avery MA, Choudhry SC, Dhingra OP, Gray BD, Kang MC, Kuo SC, Vedananda TR, White JD, Whittle AJ. Total synthesis of macrodiolide ionophores aplasmomycin A and boromycin via double ring contraction. Org Biomol Chem. 2014 Dec 7;12(45):9116-32. doi: 10.1039/c4ob01017e. PMID: 25096282. 10: Lee JJ, Chen TS, Chang CJ, Fenselau C, Floss HG. Isolation of two minor components of the boromycin fermentation: N-acetylboromycin and N-formylboromycin. J Antibiot (Tokyo). 1985 Oct;38(10):1444-6. doi: 10.7164/antibiotics.38.1444. PMID: 4066498. 11: Jayawardhana DA, Crank JA, Zhao Q, Armstrong DW, Guan X. Nanopore stochastic detection of a liquid explosive component and sensitizers using boromycin and an ionic liquid supporting electrolyte. Anal Chem. 2009 Jan 1;81(1):460-4. doi: 10.1021/ac801877g. PMID: 19055422. 12: Marsh W, Dunitz JD, White DN. Structure of a boron-free hydrolysis product from boromycin. Helv Chim Acta. 1974;57(1):10-7. doi: 10.1002/hlca.19740570103. PMID: 4465333. 13: Lakatos B, Kaiserová K, Simkovic M, Orlický J, Knézl V, Varecka L. The effect of boromycin on the Ca2+ homeostasis. Mol Cell Biochem. 2002 Feb;231(1-2):15-22. doi: 10.1023/a:1014428713997. PMID: 11952157. 14: Hütter R, Keller-Schierlein W, Knüsel F, Prelog V, Rodgers GC Jr, Suter P, Vogel G, Voser W, Zähner H. Stoffwechselprodukte von Mikroorganismen. Boromycin [The metabolic products of microorganisms. Boromycin]. Helv Chim Acta. 1967;50(6):1533-9. German. doi: 10.1002/hlca.19670500612. PMID: 6081908. 15: Rezanka T, Sigler K. Biologically active compounds of semi-metals. Phytochemistry. 2008 Feb;69(3):585-606. doi: 10.1016/j.phytochem.2007.09.018. Epub 2007 Nov 7. PMID: 17991498. 16: Pache W, Zähner H. Metabolic products of microorganisms. 77. Studies on the mechanism of action of boromycin. Arch Mikrobiol. 1969;67(2):156-65. PMID: 4247775. 17: Wang C, Armstrong DW, Risley DS. Empirical observations and mechanistic insights on the first boron-containing chiral selector for LC and supercritical fluid chromatography. Anal Chem. 2007 Nov 1;79(21):8125-35. doi: 10.1021/ac0712300. Epub 2007 Sep 25. PMID: 17892273. 18: Dong Z, Yin EG, Yang M, Zhao X, Li J, Lei W. Role and Mechanism of Keap1/Nrf2 Signaling Pathway in the Regulation of Autophagy in Alleviating Pulmonary Fibrosis. Comput Intell Neurosci. 2022 Jul 18;2022:3564871. doi: 10.1155/2022/3564871. PMID: 35898772; PMCID: PMC9313964. 19: Rosenfeld MG, Joshi MS. Effect of a rat uterine fluid endopeptidase on lysis of the zona pellucida. J Reprod Fertil. 1981 May;62(1):199-203. doi: 10.1530/jrf.0.0620199. PMID: 7014858. 20: de Carvalho LP, Niepoth E, Mavraj A, Kreidenweiss A, Herrmann J, Müller R, Knaab T, Burckhardt BB, Kurz T, Held J. Quantification of Plasmodium falciparum HPR-2 as an alternative method to [3H]hypoxanthine incorporation to measure the parasite reduction ratio in vitro. Int J Antimicrob Agents. 2023 Jun 20:106894. doi: 10.1016/j.ijantimicag.2023.106894. Epub ahead of print. PMID: 37348620.