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165440

Antimicrobial and Cytotoxicity Evaluation of New 3-Allyl-2-iminothiazolidin-4-ones

Article

Last updated: 01 Jan 2025

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-

Tags

Pharmaceutical Chemistry

Abstract

A series of novel 3-allyl-2-iminothiazolidin-4-one derivatives (4-17) was synthesized, through the reaction of 3-allyl-2-((3,4-dichlorophenyl)imino)thiazolidin-4-one (3) with different aromatic aldehydes. The chemical stability of four representative thiazolidinone derivatives (3, 11, 13 and 14) was evaluated against γ-irradiation, at a radiation dose of 25 kGy. The compounds were found to be stable with no observed degradation in liquid chromatography–mass spectrometry (LC-MS) experiments. The synthesized thiazolidinone derivatives (3-17) were evaluated for their antimicrobial and anticancer activities. Among the tested compounds, compounds 5, 7, 8, 14 and 16 exhibited slight antibacterial activity against a multi-drug resistant Staphylococcus aureus (ATCC 43300 strain), at a concentration of 32 µg/mL. Compound 3 fully inhibited the growth of the fungal pathogen Cryptococcus neoformans, at a tested concentration of 32 µg/mL. Besides, compound 12 inhibited the biofilm formation of S. aureus (HG001 strain), with a percentage of 54% at a concentration of 64 µg/mL. Compared to the other tested compounds, compound 11 showed higher in vitro anticancer activity against melanoma and breast cancer cells, with growth inhibition values ranging from 42% to 73% at a concentration of 10 µM. Interestingly, only compounds 3, 8 and 16 showed weak cytotoxicity to murine fibroblast L929 cells, at a tested concentration of 100 µM. The other tested compounds were not cytotoxic to fibroblasts, which suggests the relative safety of the synthesized compounds to normal mammalian cells.

DOI

10.21608/ejchem.2021.68822.3517

Keywords

1,3-Thiazolidin-4-one, Chemical stability, Antibacterial, Antifungal, Antibiofilm, Anticancer

Authors

First Name

Shaymaa

Last Name

Hammad

MiddleName

G.

Affiliation

Drug Radiation Research Department, National Centre for Radiation Research and Technology, Egyptian Atomic Energy Authority, Ahmed El-Zomor St. 3, El-Zohoor Dist., Nasr City, 11765 Cairo, Egypt

Email

shimaagamalhammad@gmail.com

City

-

Orcid

-

First Name

Marwa G.

Last Name

El-Gazzar

MiddleName

-

Affiliation

Drug Radiation Research Department, National Centre for Radiation Research and Technology, Egyptian Atomic Energy Authority, Ahmed El-Zomor St. 3, El-Zohoor Dist., Nasr City, 11765 Cairo, Egypt

Email

marwagalalgazzar@yahoo.com

City

-

Orcid

0000-0002-4788-5016

First Name

Mohammad

Last Name

Abdel-Halim

MiddleName

-

Affiliation

Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biotechnology, German University in Cairo, 11835 Cairo, Egypt

Email

mohammad.abdel-halim@guc.edu.eg

City

-

Orcid

0000-0003-1326-4219

First Name

Eman

Last Name

Elrazaz

MiddleName

Z.

Affiliation

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

Email

eman_elrazaz@pharm.asu.edu.eg

City

-

Orcid

0000-0003-2969-9890

First Name

Ebaa M.

Last Name

El-Hossary

MiddleName

-

Affiliation

Drug Radiation Research Department, National Centre for Radiation Research and Technology, Egyptian Atomic Energy Authority, Ahmed El-Zomor St. 3, El-Zohoor Dist., Nasr City, 11765 Cairo, Egypt

Email

ebaa.elhossary@eaea.org.eg

City

-

Orcid

0000-0002-8223-0488

First Name

Khaled A.M.

Last Name

Abouzid

MiddleName

-

Affiliation

Professor of pharmaceutical chemistry Dean of the Faculty of Pharmacy, University of Sadat City Sadat City, Menoufia, Egypt

Email

khaled.abouzid@pharma.asu.edu.eg

City

-

Orcid

0000-0001-9851-5624

Volume

64

Article Issue

9

Related Issue

27062

Issue Date

2021-09-01

Receive Date

2021-03-24

Publish Date

2021-09-01

Page Start

4,919

Page End

4,930

Print ISSN

0449-2285

Online ISSN

2357-0245

Article File

EJCHEM_Volume 64_Issue 9_Pages 4919-4930.pdf

PDF . 1.8MB

Link

https://ejchem.journals.ekb.eg/article_165440.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=165440

Order

23

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

MainTitle

Antimicrobial and Cytotoxicity Evaluation of New 3-Allyl-2-iminothiazolidin-4-ones

Details

Type

Article

Created At

22 Jan 2023