Synthesis and in vitro antimicrobial property of o-carborane derivatives

Totani, Tetsushi; Aono, Katsutoshi; Yamamoto, Kiyoe; Tawara, Katsuya

doi:10.1021/jm00144a024

Cited by 28 publications

(11 citation statements)

References 7 publications

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“…To the best of our knowledge, there is no other publication available that deals with such a topic. However, it should be noted that it has already been reported that COSAN.Na and some of the related compounds have a very high antibacterial activity against the planktonic growth of Gram-positive cocci [ 30 , 31 , 32 , 36 , 44 ]; thus, it can be used as an inhibitory agent alone. Despite this, there may be cases where a combination of antibiotics with COSAN.Na will be desirable due to their different mechanism of action.…”

Section: Discussionmentioning

confidence: 99%

“…Further studies brought positive information about the antimicrobial activity of various bis- o -dicarbaboranes, closo - o -dicarbaboranes, and nido -type dicarbollide anions towards the representatives of microscopic fungi and bacteria Staphylococcus aureus , Streptococcus pyogenes , Escherichia coli , Klebsiella pneumoniae , Mycobacterium spp., Enterobacter cloacae , Pseudomonas aeruginosa , Acinetobacter baumannii , etc. [ 36 , 37 , 38 , 39 , 40 , 41 ]. More information about these properties was published in an article focused on the antimicrobial activity of COSAN derivatives [ 32 ].…”

Section: Introductionmentioning

confidence: 99%

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Cobalt Bis-Dicarbollide Enhances Antibiotics Action towards Staphylococcus epidermidis Planktonic Growth Due to Cell Envelopes Disruption

et al. 2022

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The emergence of antibiotic resistance in opportunistic pathogens represents a huge problem, the solution for which may be a treatment with a combination of multiple antimicrobial agents. Sodium salt of cobalt bis-dicarbollide (COSAN.Na) is one of the very stable, low-toxic, amphiphilic boron-rich sandwich complex heteroboranes. This compound has a wide range of potential applications in the biological sciences due to its antitumor, anti-HIV-1, antimicrobial and antibiofilm activity. Our study confirmed the ability of COSAN.Na (in the concentration range 0.2–2.48 µg/mL) to enhance tetracycline, erythromycin, and vancomycin action towards Staphylococcus epidermidis planktonic growth with an additive or synergistic effect (e.g., the combination of 1.24 µg/mL COSAN.Na and 6.5 µg/mL TET). The effective inhibitory concentration of antibiotics was reduced up to tenfold most efficiently in the case of tetracycline (from 65 to 6.5 µg/mL). In addition, strong effect of COSAN.Na on disruption of the cell envelopes was determined using propidium iodide uptake measurement and further confirmed by transmission electron microscopy. The combination of amphiphilic COSAN.Na with antibiotics can therefore be considered a promising way to overcome antibiotic resistance in Gram-positive cocci.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cobalt Bis-Dicarbollide Enhances Antibiotics Action towards Staphylococcus epidermidis Planktonic Growth Due to Cell Envelopes Disruption

et al. 2022

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“…( 18) Minagawa, H.; Kitaura, K.; Mineura, K.; Marumo, H. Shinkin to Shinkinsho 1983, 24, 234. to in vitro and in vivo activity. Replacement of the halogen by hydrogen, methyl, and methoxy groups produces negative effects (1,4,5,10,14,15,20,21,26). Replacement of the phenyl group in R2 of I by an alkyl group (43-53) causes loss of in vitro and in vivo activity, with the retaining of some activity in Rv The size of the alkyl group in Rx plays an important role in the high activity in vivo.…”

Section: Structure-activity Relationshipsmentioning

confidence: 99%

Synthesis and oral antifungal activity of novel azolylpropanolones and related compounds

Ogata¹,

Matsumoto²,

Takahashi³

et al. 1987

J. Med. Chem.

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To find orally active antifungal agents, novel imidazolyl- and 1,2,4-triazolylpropanolones I and related compounds II-IV were synthesized. Compounds I were derived from ketones V (method A), alpha-diketone IX (method B), alpha-hydroxy ketones X (method C), alpha-chloro ketone XII (method D), and enones VI (method E). Diols II, synthesized from I with NaBH4, were cyclized to five-membered cyclic compounds III by using N,N'-carbonyldiimidazole, thionyl chloride, N,N'-(thiocarbonyl)diimidazole, bromochloromethane, 2,2-dimethoxypropane, and cyclohexanone dimethyl ketal. Diols IV were synthesized from I by Grignard reaction (method F), hydroxymethylation of X (method G), and reaction of ketones XXI with 1-[(trimethylsily)methyl]-1,2,4-triazole (method H). Compounds I-IV were examined for their antifungal activities in vitro by evaluation of broth dilution MIC values against three species of fungi and the inhibitory effect on pseudomycelium of Candida albicans, and they were examined for oral efficacy in vivo against subacute systemic candidiasis in mice and superficial dermatophytosis in guinea pigs. Compounds 2, 12, 38, 39, and 92 exhibited strong oral antifungal activity. An asymmetric synthesis and the structure-activity relationships of the compounds examined are discussed.

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“…So far, no research has to our knowledge concerned antimicrobial photodynamic effect of boronated carboranes, although photodynamic inactivation (PDI) of bacteria has long been studied with different photosensitizers [ 16 – 32 ] resulting in a great variety of medicinal applications. Of note, some data on dark bactericidal and fungicidal activity of 1-(aminoalky)-1,2-dicarba- closo -dodecaborane [ 33 ] and o -carboranylalanine [ 34 ] were earlier reported. The cytotoxic efficacy of derivatives of polyhedric boron complexes could be related to their unique binding [ 35 ] and membrane-penetrating [ 36 , 37 ] properties, the latter being associated with delocalization of their charge.…”

Section: Introductionmentioning

confidence: 99%

Carboranyl-Chlorin e6 as a Potent Antimicrobial Photosensitizer

et al. 2015

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Antimicrobial photodynamic inactivation is currently being widely considered as alternative to antibiotic chemotherapy of infective diseases, attracting much attention to design of novel effective photosensitizers. Carboranyl-chlorin-e6 (the conjugate of chlorin e6 with carborane), applied here for the first time for antimicrobial photodynamic inactivation, appeared to be much stronger than chlorin e6 against Gram-positive bacteria, such as Bacillus subtilis, Staphyllococcus aureus and Mycobacterium sp. Confocal fluorescence spectroscopy and membrane leakage experiments indicated that bacteria cell death upon photodynamic treatment with carboranyl-chlorin-e6 is caused by loss of cell membrane integrity. The enhanced photobactericidal activity was attributed to the increased accumulation of the conjugate by bacterial cells, as evaluated both by centrifugation and fluorescence correlation spectroscopy. Gram-negative bacteria were rather resistant to antimicrobial photodynamic inactivation mediated by carboranyl-chlorin-e6. Unlike chlorin e6, the conjugate showed higher (compared to the wild-type strain) dark toxicity with Escherichia coli ΔtolC mutant, deficient in TolC-requiring multidrug efflux transporters.

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Synthesis and in vitro antimicrobial property of o-carborane derivatives

Cited by 28 publications

References 7 publications

Cobalt Bis-Dicarbollide Enhances Antibiotics Action towards Staphylococcus epidermidis Planktonic Growth Due to Cell Envelopes Disruption

Cobalt Bis-Dicarbollide Enhances Antibiotics Action towards Staphylococcus epidermidis Planktonic Growth Due to Cell Envelopes Disruption

Synthesis and oral antifungal activity of novel azolylpropanolones and related compounds

Carboranyl-Chlorin e6 as a Potent Antimicrobial Photosensitizer

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