Study of Formyl and Phenyl Substituted Styrylpyrazolines: Synthesis, In Vitro Antibacterial Evaluation¸ and Molecular Docking against DNA Gyrase

Artania Adnin Tri Suma; Norman Yoshi Haryono; Navista Sri Octa Ujiantari; Adhetya Kurnia Wicaksana; Anastacia Verena Salim; Cintya Nurul Apsari; Siti Nurul Hidayah

doi:10.22146/ijp.20388

Artania Adnin Tri Suma Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Gadjah Mada
Norman Yoshi Haryono Biotechnology Study Program, Department of Applied Science, Faculty of Mathematics and Natural Sciences, Universitas Negeri Malang
Navista Sri Octa Ujiantari Laboratory of Medicinal Chemistry, Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Gadjah Mada
Adhetya Kurnia Wicaksana Laboratory of Medicinal Chemistry, Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Gadjah Mada
Anastacia Verena Salim Biotechnology Study Program, Department of Applied Science, Faculty of Mathematics and Natural Sciences, Universitas Negeri Malang
Cintya Nurul Apsari Laboratory of Medicinal Chemistry, Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Gadjah Mada
Siti Nurul Hidayah Laboratory of Analytical Chemistry, Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Gadjah Mada

DOI: https://doi.org/10.22146/ijp.20388

Keywords: styrylpyrazoline, antibacterial, DNA gyrase, docking

Abstract

Bacterial resistance to most antibiotics remains a persistent challenge, urging the need for the development of novel antibacterial agents. Styrylpyrazoline derivatives have shown diverse biological activity, including as an antibacterial. This study synthesized and evaluated styrypyrazolines 2a and 2b for their antibacterial activity against Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa). The in vitro evaluation was performed using disc diffusion and microdilution methods. The result revealed that both compounds have the highest inhibition against S. aureus. Moreover, the presence of formyl group (-CHO) on styrylpyrazoline 2a enhanced its inhibitory activity against P. aeruginosa. Neither compound showed significant inhibition against B. subtilis or S. epidermidis. Molecular docking of both compounds against DNA gyrase subunit B was performed to further investigate their antibacterial mechanism. It was revealed that both compounds are able to interact with the receptor within the ATP-binding pocket. Similar to ciprofloxacin, compound 2a formed hydrogen bonds with the Asp81 residue, showing its potential as a DNA gyrase inhibitor. While compound 2b formed aromatic-hydrogen bridging with Pro87 residue. This study suggests that styrypyrazolines 2a and 2b possess promising antibacterial activity. However, their potency is lower than the reference drug. Thus, further modification of the structure is necessary to enhance their potency as antibacterial agents.

Keywords: styrylpyrazoline, antibacterial, DNA gyrase, docking

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