Effect of Methyl-β-Cyclodextrin on the antimicrobial activity of a new series of poorly water-soluble benzothiazoles

Trapani, Adriana; Catalano, Alessia; Carocci, Alessia; Carrieri, Antonio; Mercurio, Annalisa; Rosato, Antonio; Mandracchia, Delia; Tripodo, Giuseppe; Schiavone, Brigida Immacolata Pia; Franchini, Carlo; Mesto, Ernesto; Schingaro, Emanuela; Corbo, Filomena

doi:10.1016/j.carbpol.2018.12.016

Cited by 32 publications

(13 citation statements)

References 36 publications

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“…In the search for new diarylurea analogues more potent as antibacterials than TCC, we sought to analyze new small molecules bearing an aryl moiety different from phenyl. Several nuclei for replacing the phenyl group were considered, finally choosing the benzothiazole (BTA) one that is known to have antimicrobial properties [28][29][30]. BTA is a fused benzoheterocyle present in many naturally occurring and synthetic products and responsible for the medicinal, pharmacological and pharmaceutical applications, including neuroprotective, antidiabetic, antitumor, antimalarial, antitubercular and antimicrobial [31].…”

Section: Introductionmentioning

confidence: 99%

Benzothiazole-Containing Analogues of Triclocarban with Potent Antibacterial Activity

et al. 2021

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Triclocarban (TCC) is a polychlorinated, aromatic, antimicrobial agent commercially used since the 1950s in personal care products for the prevention of spoilage and infections. Humans are frequently exposed to TCC due to its widespread use, leading to its substantial release into the aquatic environment. With the recent ban of TCC from some personal care products, implemented in 2016, many replacement antimicrobial compounds have been studied by researchers. Herein, we report the synthesis and biological activity of a series of diarylureas, analogues of TCC that bear the benzothiazole nucleus as one of the two aryl moieties. Among the studied compounds, 2bF and 2eC showed the highest antimicrobial activity against Staphylococcus aureus, being also more active than TCC, with MIC values of 8 µg/mL versus 16 µg/mL of TCC. Moreover, compound 2bB was much more active than TCC against Enterococcus faecalis, a Gram-positive bacterium that is, unfortunately, strongly responsible for nosocomial infections. Finally, interesting results were found for compound 2bG that, even though less active than the others, exerts an interesting bactericidal action.

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Section: Introductionmentioning

confidence: 99%

Benzothiazole-Containing Analogues of Triclocarban with Potent Antibacterial Activity

et al. 2021

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“…Enhanced solubility and antibacterial activity of S ‐unsubstituted benzothiazoles were observed on complexation with methyl‐β‐Cyclodextrin (Me‐β‐CD) [40] . In another study, superior DNA (Deoxyribonucleic acid) tethering and antimicrobial activity [41] of Copper(II)‐complexes of 2‐benzo[ d ]thiazol‐6‐ylimino)methyl)benzene‐1,4‐diol was observed, which was attributed to non‐covalent and intercalative interaction of metal complexes with DNA base pairs.…”

Section: Introductionmentioning

confidence: 99%

Solid‐Supported Materials‐Based Synthesis of 2‐Substituted Benzothiazoles: Recent Developments and Sanguine Future

et al. 2021

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Benzothiazole and its derivatives have been manifested as an optimistic scaffold due to their immense biological importance. Several methodologies have been reported as modifications after the first report of 2-substituted benzothiazole. Among them, many involve a shift from the conventional synthetic approach by utilizing different catalytic systems. Moreover, synthetic methodologies focused on improvements in terms of product yield, reaction duration, use of environmentally benign conditions and simplified workup procedures predominate among the recently developed approaches. Solid-phase organic synthesis received considerable attention with the pioneering findings of Merrifield's solid-phase peptide synthesis in 1963. A diverse range of organic, inorganic and organic-inorganic substances have been utilized as polymeric solid supports in various catalytic applications. The recyclability and reusability of the immobilized catalysts over consecutive cycles establish them as an attractive alternative over conventional catalytic systems from the environment as well as industrial perspective. The present review summarizes the recent developments in the environmentally benign synthesis of benzothiazole derivatives using supported reagents. Different solid supports along with their catalytic application, mechanistic perspective and substrate tolerance have been discussed comprehensively.

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“…The benzothiazole nucleus, with a variety of modifications, has demonstrated a wide range of pharmacological properties including antimicrobial [5], anti-HIV [6], anthelmintic [7], antidiabetic [8], anticonvulsant [9], larvicidal [10], antimalarial [11], and anticancer activities [12]. In addition, the potential antimicrobial activity of benzothiazole derivatives was previously illustrated [13][14][15][16][17]. The results of these studies concluded that the antimicrobial activity of benzothiazole derivatives can be attributed to its ability to interact with several cellular targets including Staphylococcus (S.) aureus DNA gyrase [18][19][20], Escherichia (E.) coli dihydropteroate synthase [21], Plasmodium dihydrofolate reductase [22], and, recently, E. coli dihydroorotase [23].…”

Section: Introductionmentioning

confidence: 99%

Screening and Molecular Docking of Novel Benzothiazole Derivatives as Potential Antimicrobial Agents

et al. 2020

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The burden of antibiotic resistance necessitates a continued search for new antimicrobials. We evaluated the antimicrobial activities of novel benzothiazoles synthesized by our group. Antibacterial activity was evaluated in vitro in Staphylococcus aureus, Bacillus subtilis, and Escherichia coli, while the antifungal activity was tested in Candida albicans and Aspergillus niger, and expressed as the minimum inhibitory concentration (MIC; µg/mL). MIC values of benzothiazole compounds ranged from 25 to 200 µg/mL. Compounds 3 and 4 gave high antibacterial and moderate antifungal activities, while 10 and 12 showed moderate activity against all tested organisms. In addition, some benzothiazole compounds significantly suppressed the activity of Escherichia coli dihydroorotase and inhibited the dimorphic transition of Candida albicans. Moreover, the active benzothiazole compounds induced DNA and protein leakage in Aspergillus niger spores. Molecular interactions of benzothiazole derivatives with dihydroorotase revealed the formation of hydrogen bonds with the active site residues LEU222 or ASN44. Strong hydrophobic interactions of the bulky thiazole and naphthalene rings at the entrance to the active site might interfere with the access of substrates to their binding sites, which results in dihydroorotase inhibition. Thus, inhibition of dihydroorotase might contribute to the observed antimicrobial actions of these compounds.

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Effect of Methyl-β-Cyclodextrin on the antimicrobial activity of a new series of poorly water-soluble benzothiazoles

Cited by 32 publications

References 36 publications

Benzothiazole-Containing Analogues of Triclocarban with Potent Antibacterial Activity

Benzothiazole-Containing Analogues of Triclocarban with Potent Antibacterial Activity

Solid‐Supported Materials‐Based Synthesis of 2‐Substituted Benzothiazoles: Recent Developments and Sanguine Future

Screening and Molecular Docking of Novel Benzothiazole Derivatives as Potential Antimicrobial Agents

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