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Volume 17
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Article

Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C

by
Patrick Rômbola Ozanique
1,
Alvaro Luiz Helena
1,
Ralciane de Paula Menezes
2,
Daniela Silva Gonçalves
2,
Mariana Brentini Santiago
2,
Guilherme Dilarri
3,
Janaína de Cássia Orlandi Sardi
4,
Henrique Ferreira
3,
Carlos Henrique Gomes Martins
2 and
Luis Octávio Regasini
1,*
1
Department of Chemistry and Environmental Sciences, Institute of Biosciences, Humanities and Exact Sciences, São Paulo State University (Unesp), São José do Rio Preto 15054-000, SP, Brazil
2
Department Microbiology, Institute of Biomedical Sciences, Federal University of Uberlândia (UFU), Umuarama 38405-320, MG, Brazil
3
Department of Biochemistry and Microbiology, Institute of Biosciences, São Paulo State University (Unesp), Rio Claro 13506-900, SP, Brazil
4
Dental Research Division, Guarulhos University, Guarulhos 07023-070, SP, Brazil
*
Author to whom correspondence should be addressed.
Pharmaceuticals 2024, 17(5), 634; https://doi.org/10.3390/ph17050634
Submission received: 30 March 2024 / Revised: 11 May 2024 / Accepted: 12 May 2024 / Published: 14 May 2024
(This article belongs to the Special Issue Recent Developments of Chalcones and Their Derivatives in Medicinal Chemistry)
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Abstract

Drug-resistant bacteria constitute a big barrier against current pharmacotherapy. Efforts are urgent to discover antibacterial drugs with novel chemical and biological features. Our work aimed at the synthesis, evaluation of antibacterial effects, and toxicity of licochalcone C (LCC), a naturally occurring chalcone. The synthetic route included six steps, affording a 10% overall yield. LCC showed effects against Gram-positive bacteria (MIC = 6.2–50.0 µg/mL), Mycobacterium species (MIC = 36.2–125 µg/mL), and Helicobacter pylori (MIC = 25 µg/mL). LCC inhibited the biofilm formation of MSSA and MRSA, demonstrating MBIC50 values of 6.25 μg/mL for both strains. The investigations by fluorescence microscopy, using PI and SYTO9 as fluorophores, indicated that LCC was able to disrupt the S. aureus membrane, similarly to nisin. Systemic toxicity assays using Galleria mellonella larvae showed that LCC was not lethal at 100 µg/mL after 80 h treatment. These data suggest new uses for LCC as a compound with potential applications in antibacterial drug discovery and medical device coating.
Keywords: licochalcone; chalcone; Glycyrrhiza; membrane; biofilm; antibacterial; drug-resistant; Galleria mellonella licochalcone; chalcone; Glycyrrhiza; membrane; biofilm; antibacterial; drug-resistant; Galleria mellonella

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MDPI and ACS Style

Ozanique, P.R.; Helena, A.L.; Menezes, R.d.P.; Gonçalves, D.S.; Santiago, M.B.; Dilarri, G.; Sardi, J.d.C.O.; Ferreira, H.; Martins, C.H.G.; Regasini, L.O. Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C. Pharmaceuticals 2024, 17, 634. https://doi.org/10.3390/ph17050634

AMA Style

Ozanique PR, Helena AL, Menezes RdP, Gonçalves DS, Santiago MB, Dilarri G, Sardi JdCO, Ferreira H, Martins CHG, Regasini LO. Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C. Pharmaceuticals. 2024; 17(5):634. https://doi.org/10.3390/ph17050634

Chicago/Turabian Style

Ozanique, Patrick Rômbola, Alvaro Luiz Helena, Ralciane de Paula Menezes, Daniela Silva Gonçalves, Mariana Brentini Santiago, Guilherme Dilarri, Janaína de Cássia Orlandi Sardi, Henrique Ferreira, Carlos Henrique Gomes Martins, and Luis Octávio Regasini. 2024. "Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C" Pharmaceuticals 17, no. 5: 634. https://doi.org/10.3390/ph17050634

APA Style

Ozanique, P. R., Helena, A. L., Menezes, R. d. P., Gonçalves, D. S., Santiago, M. B., Dilarri, G., Sardi, J. d. C. O., Ferreira, H., Martins, C. H. G., & Regasini, L. O. (2024). Synthesis, Antibacterial Effects, and Toxicity of Licochalcone C. Pharmaceuticals, 17(5), 634. https://doi.org/10.3390/ph17050634

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