Metallacarborane Assemblies as Effective Antimicrobial Agents, Including a Highly Potent Anti-MRSA Agent

Romero, Isabel; Martinez-Medina, Margarita; Camprubí-Font, Carla; Bennour, Ines; Moreno, David; Martínez-Martínez, Luis; Teixidor, Francesc; Fox, Mark A.; Viñas, Clara

Abstract

The salts Na[ROC(O)Ph], Na[1-ROC(O)-1,12-C2B10H11], K2[1,4-(ROC(O))2-C6H4], and K2[1,12-(ROC(O))2-1,12-C2B10H10], where R is the cobaltabis(dicarbollide)-diethylene glycol group [3,3′-Co(8-(OCH2CH2OCH2CH2)-1,2-C2B9H10)(1′,2′-C2B9H11)]−, were synthesized from the corresponding carboxylate salt and the zwitterion [3,3′-Co(8-(CH2CH2O)2-1,2-C2B9H10)(1′,2′-C2B9H11)]. The dianion in K2[1,12-(ROC(O))2-1,12-C2B10H10] showed at least one K+ cation to be tightly bound to the dianion via K···O and K···H–B interactions with both p-carborane and cobaltabis(dicarbollide) clusters on the basis of NMR and MS data and support of hybrid-DFT computations. An evaluation of the antimicrobial properties of these compounds revealed all of the salts to be highly effective antibacterial agents for four Gram-positive bacteria strains (standard minimum inhibitory concentration, MIC, of 1 mg/L for Na[ROC(O)Ph]; Na[3]) and antifungal agents for three Candida albicans strains (MIC 4 mg/L for the salts K2[4] and K2[6]). One of the four Gram-positive bacteria strains tested was a life-threatening superbug methicillin-resistant Staphylococcus aureus (MRSA) isolate, which is resistant to many commercial antimicrobial drugs. The cobaltabis(dicarbollide) derivative Na[3] has a remarkable inhibitory effect on the MRSA strain with an MIC of only 1 mg/L and a minimum bactericidal concentration (MBC) of 2 mg/L, thus suggesting its potential as an antibacterial agent against MRSA.

Citation

Romero, I., Martinez-Medina, M., Camprubí-Font, C., Bennour, I., Moreno, D., Martínez-Martínez, L., Teixidor, F., Fox, M. A., & Viñas, C. (2020). Metallacarborane Assemblies as Effective Antimicrobial Agents, Including a Highly Potent Anti-MRSA Agent. Organometallics, 39(23), 4253-4264. https://doi.org/10.1021/acs.organomet.0c00315

• Journal Article Type: Article
• Acceptance Date: Jun 25, 2020
• Online Publication Date: Jul 9, 2020
• Publication Date: 2020
• Deposit Date: Jul 21, 2020
• Publicly Available Date: Jul 9, 2021
• Journal: Organometallics
• Print ISSN: 0276-7333
• Electronic ISSN: 1520-6041
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 39
• Issue: 23
• Pages: 4253-4264
• DOI: https://doi.org/10.1021/acs.organomet.0c00315
• Public URL: https://durham-repository.worktribe.com/output/1265962