N-(2-Arylmethylthio-4-Chloro-5-Methylbenzenesulfonyl)amide Derivatives as Potential Antimicrobial Agents—Synthesis and Biological Studies

Żołnowska, Beata; Sławiński, Jarosław; Garbacz, Katarzyna; Jarosiewicz, Małgorzata; Kawiak, Anna

doi:10.3390/ijms21010210

Open AccessArticle

N-(2-Arylmethylthio-4-Chloro-5-Methylbenzenesulfonyl)amide Derivatives as Potential Antimicrobial Agents—Synthesis and Biological Studies

by

Beata Żołnowska

^1,*

,

Jarosław Sławiński

^1,*

,

Katarzyna Garbacz

²,

Małgorzata Jarosiewicz

²

and

Anna Kawiak

³

¹

Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland

²

Department of Oral Microbiology, Faculty of Medicine, Medical University of Gdańsk, Dębowa 25, 80-204 Gdańsk, Poland

³

Department of Biotechnology, Intercollegiate Faculty of Biotechnology, University of Gdańsk and Medical University of Gdańsk, Ul. Abrahama 58, 80-307 Gdańsk, Poland

^*

Authors to whom correspondence should be addressed.

Int. J. Mol. Sci. 2020, 21(1), 210; https://doi.org/10.3390/ijms21010210

Submission received: 9 December 2019 / Revised: 20 December 2019 / Accepted: 21 December 2019 / Published: 27 December 2019

(This article belongs to the Section Biochemistry)

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Abstract

Rising resistance of pathogenic bacteria reduces the options of treating hospital and non-hospital bacterial infections. There is a need to search for newer chemotherapies that will show antimicrobial ability against planktonic cells as well as bacterial biofilms. We have synthesized a series of N-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)amides, namely, molecular hybrids, which include a 2-mercaptobenzenosulfonamide fragment and either cinnamic or cyclohexylpropionic acid residues. The antimicrobial activity of compounds 8–17 was evaluated on Gram-positive, Gram-negative bacteria and fungal species. Experiments took into account investigation of antibacterial activity against planktonic cells as well as biofilms. Compounds 8–17 showed high bacteriostatic activity against staphylococci, with the most active molecules 10 and 16 presenting low MIC values of 4–8 μg/mL against reference methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-sensitive S. aureus (MSSA) strains as well as clinical isolates. Compounds 10 and 16 also showed an ability to inhibit biofilms formed by MRSA and MSSA. The potential of 10 and 16 as antibiofilm agents was supported by cytotoxicity assays that indicated no cytotoxic effect either on normal cells of human keratinocytes or on human cancer cells, including cervical, colon, and breast cancer lines.

Keywords: benzenesulfonamide; antibacterial; biofilm; synthesis; cytotoxicity; MRSA

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MDPI and ACS Style

Żołnowska, B.; Sławiński, J.; Garbacz, K.; Jarosiewicz, M.; Kawiak, A. N-(2-Arylmethylthio-4-Chloro-5-Methylbenzenesulfonyl)amide Derivatives as Potential Antimicrobial Agents—Synthesis and Biological Studies. Int. J. Mol. Sci. 2020, 21, 210. https://doi.org/10.3390/ijms21010210

AMA Style

Żołnowska B, Sławiński J, Garbacz K, Jarosiewicz M, Kawiak A. N-(2-Arylmethylthio-4-Chloro-5-Methylbenzenesulfonyl)amide Derivatives as Potential Antimicrobial Agents—Synthesis and Biological Studies. International Journal of Molecular Sciences. 2020; 21(1):210. https://doi.org/10.3390/ijms21010210

Chicago/Turabian Style

Żołnowska, Beata, Jarosław Sławiński, Katarzyna Garbacz, Małgorzata Jarosiewicz, and Anna Kawiak. 2020. "N-(2-Arylmethylthio-4-Chloro-5-Methylbenzenesulfonyl)amide Derivatives as Potential Antimicrobial Agents—Synthesis and Biological Studies" International Journal of Molecular Sciences 21, no. 1: 210. https://doi.org/10.3390/ijms21010210

APA Style

Żołnowska, B., Sławiński, J., Garbacz, K., Jarosiewicz, M., & Kawiak, A. (2020). N-(2-Arylmethylthio-4-Chloro-5-Methylbenzenesulfonyl)amide Derivatives as Potential Antimicrobial Agents—Synthesis and Biological Studies. International Journal of Molecular Sciences, 21(1), 210. https://doi.org/10.3390/ijms21010210

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N-(2-Arylmethylthio-4-Chloro-5-Methylbenzenesulfonyl)amide Derivatives as Potential Antimicrobial Agents—Synthesis and Biological Studies

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