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Open AccessArticle

4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents

1
Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
2
Department of Biological and Medical Sciences, Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
3
Department of Pharmacology and Toxicology, Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
4
Unipetrol Centre of Research and Education, 436 70 Litvínov-Záluží 1, Czech Republic
5
Laboratory for Mycobacterial Diagnostics and Tuberculosis, Regional Institute of Public Health in Ostrava, Partyzánské námĕstí 7, 702 00 Ostrava, Czech Republic
*
Author to whom correspondence should be addressed.
Biomolecules 2020, 10(1), 9; https://doi.org/10.3390/biom10010009
Received: 5 November 2019 / Revised: 11 December 2019 / Accepted: 17 December 2019 / Published: 19 December 2019
4-aminobenzoic acid (PABA), an essential nutrient for many human pathogens, but dispensable for humans, and its derivatives have exhibited various biological activities. In this study, we combined two pharmacophores using a molecular hybridization approach: this vitamin-like molecule and various aromatic aldehydes, including salicylaldehydes and 5-nitrofurfural, via imine bond in one-step reaction. Resulting Schiff bases were screened as potential antimicrobial and cytotoxic agents. The simple chemical modification of non-toxic PABA resulted in constitution of antibacterial activity including inhibition of methicillin-resistant Staphylococcus aureus (minimum inhibitory concentrations, MIC, from 15.62 µM), moderate antimycobacterial activity (MIC ≥ 62.5 µM) and potent broad-spectrum antifungal properties (MIC of ≥ 7.81 µM). Some of the Schiff bases also exhibited notable cytotoxicity for cancer HepG2 cell line (IC50 ≥ 15.0 µM). Regarding aldehyde used for the derivatization of PABA, it is possible to tune up the particular activities and obtain derivatives with promising bioactivities. View Full-Text
Keywords: 4-aminobenzoic acid; antibacterial activity; antifungal activity; cytotoxicity; Schiff bases; synthesis; vitamin 4-aminobenzoic acid; antibacterial activity; antifungal activity; cytotoxicity; Schiff bases; synthesis; vitamin
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MDPI and ACS Style

Krátký, M.; Konečná, K.; Janoušek, J.; Brablíková, M.; Janďourek, O.; Trejtnar, F.; Stolaříková, J.; Vinšová, J. 4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents. Biomolecules 2020, 10, 9.

AMA Style

Krátký M, Konečná K, Janoušek J, Brablíková M, Janďourek O, Trejtnar F, Stolaříková J, Vinšová J. 4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents. Biomolecules. 2020; 10(1):9.

Chicago/Turabian Style

Krátký, Martin; Konečná, Klára; Janoušek, Jiří; Brablíková, Michaela; Janďourek, Ondřej; Trejtnar, František; Stolaříková, Jiřina; Vinšová, Jarmila. 2020. "4-Aminobenzoic Acid Derivatives: Converting Folate Precursor to Antimicrobial and Cytotoxic Agents" Biomolecules 10, no. 1: 9.

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