Boromycin
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| Category | Antibiotics |
| Catalog number | BBF-00582 |
| CAS | 34524-20-4 |
| Molecular Weight | 879.87 |
| Molecular Formula | C45H74BNO15 |
| Purity | >98% |
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Description
Boromycin is a boron-containing antibiotic produced by Streptomyces antibioticua. It has anti-gram-positive bacteria activity, and has the effect of inhibiting malaria parasites and killing coccidia.
Specification
| Synonyms | NSC 121380 |
| Storage | Store at -20°C |
| IUPAC Name | [(2R)-1-[(1R)-1-[(1R,5S,7E,11S,13S,16R,17R,24S,25R,27R,31R,33S,36R)-11,31-dihydroxy-12,12,16,25,32,32,36-heptamethyl-3,22-dioxo-4,18,20,23,26,37,38,40,41-nonaoxa-19-boranuidaheptacyclo[17.17.1.11,33.12,19.113,17.124,27.017,21]hentetracont-7-en-5-yl]ethoxy]-3-methyl-1-oxobutan-2-yl]azanium |
| Canonical SMILES | [B-]123OC4C(=O)OC(CC=CCCC(C(C5CCC(C(O1)(O5)C(O2)C(=O)OC6CC(CCCC(C(C7CCC(C4(O3)O7)C)(C)C)O)OC6C)C)(C)C)O)C(C)OC(=O)C(C(C)C)[NH3+] |
| 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 |
| InChI Key | OOBFYEMEQCZLJL-XURNZCJASA-O |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; parasites |
| Melting Point | 223-228°C(dec.) |
| Solubility | Soluble in DMSO |
Reference Reading
1. Boromycin Has Potent Anti- Toxoplasma and Anti- Cryptosporidium Activity
Roberta O'Connor, Alexis Cotto-Rosario, Jaypee Abenoja Antimicrob Agents Chemother . 2021 Mar 18;65(4):e01278-20. doi: 10.1128/AAC.01278-20.
Toxoplasma gondiiandCryptosporidium parvum, members of the phylum Apicomplexa, are significant pathogens of both humans and animals worldwide for which new and effective therapeutics are needed. Here, we describe the activity of the antibiotic boromycin againstToxoplasmaandCryptosporidiumBoromycin potently inhibited intracellular proliferation of bothT. gondiiandC. parvumat half-maximal effective concentrations (EC50) of 2.27 nM and 4.99 nM, respectively. Treatment of extracellularT. gondiitachyzoites with 25 nM boromycin for 30 min suppressed 84% of parasite growth, butT. gondiitachyzoite invasion into host cells was not affected by boromycin. Immunofluorescence of boromycin-treatedT. gondiishowed loss of morphologically intact parasites with randomly distributed surface antigens inside the parasitophorous vacuoles. Boromycin exhibited a high selectivity for the parasites over their host cells. These results suggest that boromycin is a promising new drug candidate for treating toxoplasmosis and cryptosporidiosis.
2. Boromycin abrogates bleomycin-induced G2 checkpoint
Takumi Kawabe, Yukio Koizumi, Masashi Suganuma, Masayoshi Arai, Hiroshi Tomoda, Satoshi Omura, Hidetaka Kobayashi, Hitoshi Sato J Antibiot (Tokyo) . 2004 Oct;57(10):662-8. doi: 10.7164/antibiotics.57.662.
The DNA-damaging agent bleomycin arrests the cell cycle at the G2 phase of Jurkat cells defective in the G1 checkpoint, and microtubule-acting colchicine arrests it at the M phase. Boromycin itself, an actinomycete metabolite, showed no effect on the cell cycle status of Jurkat cells at least up to 340 nM. However, the compound (3.4-340 nM) was found to abrogate bleomycin-induced G2 arrest even at 3.4 nM, resulting in a drastic decrease in cells at the G2 phase and increase in cells at the subG1 phase. On the other hand, boromycin did not show any effect on the colchicine-induced M phase arrest in Jurkat cells, nor on the cell cycle status of the bleomycin-treated or -untreated HUVEC, normal cells conserving both G1 and G2 checkpoints. Furthermore, boromycin potentiated anti-tumor activity of bleomycin in scid mice inoculated with Jurkat cells. These data suggest that boromycin disrupts the cell cycle at the G2 checkpoint of cancer cells selectively, leading to sensitization of cancer cells to anti-cancer reagents.
3. Boromycin Kills Mycobacterial Persisters without Detectable Resistance
Wilfried Moreira, Dinah B Aziz, Thomas Dick Front Microbiol . 2016 Feb 22;7:199. doi: 10.3389/fmicb.2016.00199.
Boromycin is a boron-containing polyether macrolide antibiotic isolated from Streptomyces antibioticus. It was shown to be active against Gram positive bacteria and to act as an ionophore for potassium ions. The antibiotic is ineffective against Gram negative bacteria where the outer membrane appears to block access of the molecule to the cytoplasmic membrane. Here we asked whether boromycin is active against Mycobacterium tuberculosis which, similar to Gram negative bacteria, possesses an outer membrane. The results show that boromycin is a potent inhibitor of mycobacterial growth (MIC50 = 80 nM) with strong bactericidal activity against growing and non-growing drug tolerant persister bacilli. Exposure to boromycin resulted in a rapid loss of membrane potential, reduction of the intracellular ATP level and leakage of cytoplasmic protein. Consistent with boromycin acting as a potassium ionophore, addition of KCl to the medium blocked its antimycobacterial activity. In contrast to the potent antimycobacterial activities of the polyether macrolide, its cytotoxicity and haemolytic activity were low (CC50 = 30 μM, HC50 = 40 μM) with a selectivity index of more than 300. Spontaneous resistant mutants could not be isolated suggesting a mutation frequency of less than 10(-9)/CFU. Taken together, the results suggests that targeting mycobacterial transmembrane ion gradients may be an attractive chemotherapeutic intervention level to kill otherwise drug tolerant persister bacilli, and to slow down the development of genetic antibiotic resistance.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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