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185469

Synthesis, In Silico and In Vitro Antimicrobial Evaluation of Cyanoketene S,N-Acetals and their Pyrazoles Against <i>Staphylococcus aureus</i> DNA Gyrase Enzyme

Article

Last updated: 03 Jan 2025

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Subjects

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Tags

Section E: Microbiology & Immunology

Abstract

Objectives: The continuous reporting of bacterial resistance to antibiotics is an ongoing challenge that can be life-threatening. Actions to develop new chemicals to overcome the bacterial resistance has gained a significant importance. Methods: A series of ketene S,N-acetals 4a-k and their pyrazoles 6a-k were synthesized and their structures were established by spectral data. Membrane permeability predictions and in vitro antimicrobial activity against multi-drug resistant (MDR) Gram-positive bacteria and other microorganisms was determined. The binding affinity with DNA gyrase was assessed using in silico studies in comparison to ciprofloxacin then tthe gyrase inhibition assay was conducted to detect the mode of action. Results: All the synthesized compounds have a good affinity to pass through the phospholipid membrane of Staphylococcus aureus (S. aureus). Compound 6g exhibited the most potent antibacterial activity with MIC values ranged between 16 and 32 µg/mL. The compound also showed a higher binding affinity than ciprofloxacin with DNA gyrase in the in silico studies and this effect was clearly shown by a very good IC50 value of the gyrase inhibition assay. Conclusions: According to our data, compound 6g is a possible candidate to act against MDR bacteria and its main mode of action is through inhibition of the gyrase enzyme, further modifications are still required to enhance its activity.

DOI

10.21608/aprh.2021.76173.1130

Keywords

Acrylamide, 5-Aminopyrazole, DNA Gyrase, Multi-drug resistance

Authors

First Name

Shima

Last Name

Ali

MiddleName

Mahmoud

Affiliation

Department of Microbiology and Immunology, Faculty of Pharmacy, Helwan University, Egypt.

Email

shaima.mn@gmail.com

City

-

Orcid

-

First Name

Ahmed

Last Name

H.I. Faraag

MiddleName

-

Affiliation

Botany and Microbiology Department, Faculty of Science, Helwan University, Ain Helwan, Egypt.

Email

professor.ahmed85@gmail.com

City

-

Orcid

-

First Name

Hossam

Last Name

Elgiushy

MiddleName

R.

Affiliation

Pharmaceutical Chemistry Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt.

Email

hussamelgiushy@hotmail.com

City

nasr city cairo

Orcid

-

First Name

Taghrid

Last Name

El-Mahdy

MiddleName

S.

Affiliation

Department of Microbiology and Immunology, Faculty of Pharmacy, Helwan University, Egypt., Department of Microbiology and Immunology, Faculty of Pharmacy, Ahram Canadian University, Giza, Egypt.

Email

sata186@hotmail.com

City

-

Orcid

-

First Name

Ahmed

Last Name

Askar

MiddleName

A.

Affiliation

Botany and Microbiology Department, Faculty of Science (Boys), Al-Azhar University, Cairo, Egypt.

Email

drahmed_askr@yahoo.com

City

-

Orcid

-

First Name

Ashraf

Last Name

Hassan

MiddleName

S.

Affiliation

Department of Organometallic and Organometalloid Chemistry, National Research Centre, Dokki 12622, Cairo, Egypt.

Email

ashraf_salmoon@yahoo.com

City

cairo

Orcid

0000-0002-4771-716X

First Name

Khaled

Last Name

Abouzid

MiddleName

A. M.

Affiliation

Pharmaceutical Chemistry Department, Faculty of Pharmacy, Ain Shams University, Cairo 11566, Egypt.

Email

khaled.abouzid@pharma.asu.edu.eg

City

Cairo

Orcid

-

First Name

Sherif

Last Name

Hammad

MiddleName

F.

Affiliation

Pharmaceutical Chemistry Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt. , Basic and Applied Sciences Institute, Egypt-Japan University of Science and Technology (E-JUST), New Borg El-Arab City, 21934 Alexandria, Egypt.

Email

sherifhammad2010@hotmail.com

City

-

Orcid

-

Volume

5

Article Issue

3

Related Issue

26911

Issue Date

2021-07-01

Receive Date

2021-05-13

Publish Date

2021-07-01

Page Start

341

Page End

361

Print ISSN

2357-0547

Online ISSN

2357-0539

Article File

APRH_Volume 5_Issue 3_Pages 341-361.pdf

PDF . 1.8MB

Link

https://aprh.journals.ekb.eg/article_185469.html

Detail API

https://aprh.journals.ekb.eg/service?article_code=185469

Order

6

Type

Research Article

Type Code

318

Publication Type

Journal

Publication Title

Journal of Advanced Pharmacy Research

Publication Link

https://aprh.journals.ekb.eg/

MainTitle

Synthesis, In Silico and In Vitro Antimicrobial Evaluation of Cyanoketene S,N-Acetals and their Pyrazoles Against <i>Staphylococcus aureus</i> DNA Gyrase Enzyme

Details

Type

Article

Created At

22 Jan 2023