Bromophene
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| Names | |
|---|---|
| Preferred IUPAC name
3,3′,5,5′-Tetrabromo[1,1′-biphenyl]-2,2′-diol | |
| Other names
MC21-A; C58; 2,2'-Dihydroxy-3,3',5,5'-tetrabromobiphenyl; 3,3',5,5'-Tetrabromo-2,2'-biphenyldiol | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.161.669 |
| MeSH | 3,3',5,5'-tetrabromo-2,2'-biphenyldiol |
PubChem CID |
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C12H6Br4O2 | |
| Molar mass | 501.794 g·mol−1 |
| Appearance | White, needle-like crystals or white powder. (Crystallization from acetone, EtOH or CHCl3) |
| Melting point | 205 to 207 °C (401 to 405 °F; 478 to 480 K) |
| Sol. DMSO, Acetone, CHCl3 Slightly Sol. EtOH, MeOH Insol. H2O, hexane | |
| Related compounds | |
Related biphenyls |
MC21-B Polybrominated biphenyl |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bromophene (MC21-A or C58) is a bactericidal antibiotic first isolated from the O-BC30 strain of a marine bacterium, Pseudoalteromonas phenolica.[1] A 2024 study reported that bromophene exhibited antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA), with a minimum inhibitory concentration of 2 μg/mL against 39 different isolates. In the same study, bromophene exhibited in vitro antibacterial activity comparable to or greater than that of daptomycin, vancomycin, and linezolid under the conditions tested.[2] Additionally, bromophene eradicated established MRSA biofilms at a concentration of 8 μg/mL in vitro, whereas vancomycin did not achieve partial biofilm eradication at the concentrations evaluated in the same study.[2]
Mechanism of Action
[edit]The mechanism of action for bromophene has not been fully elucidated. However, previous reports describe increased bacterial membrane permeability without cell lysis.[1][2]
References
[edit]- 1 2 Isnansetyo, Alim; Kamei, Yuto (February 2003). "MC21-A, a Bactericidal Antibiotic Produced by a New Marine Bacterium, Pseudoalteromonas phenolica sp. nov. O-BC30T, against Methicillin-Resistant Staphylococcus aureus". Antimicrobial Agents and Chemotherapy. 47 (2). Washington, DC: American Society for Microbiology: 480–488. doi:10.1128/AAC.47.2.480-488.2003. ISSN 1098-6596. OCLC 678833406. PMC 151744. PMID 12543647.
- 1 2 3 Shah KN, Shah PN, Agobe FO, Lovato K, Gao H, Ogun O, Hoffman C, Yabe-Gill M, Chen Q, Sweatt J, Chirra B, Muñoz-Medina R, Farmer DE, Kürti L, Cannon CL. 2024. Antimicrobial activity of a natural compound and analogs against multi-drug-resistant Gram-positive pathogens. Microbiology Spectrum 12:e01515-22. https://doi.org/10.1128/spectrum.01515-22
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