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312100

The Effect of Fatty Alkanolamide Structure on Cytotoxic and Antimicrobial Activity

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Last updated: 01 Jan 2025

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Abstract

This research was conducted to explore the prospect of fatty acid derivatives as candidates for anticancer and antimicrobial drugs. Synthesis of fatty alkanolamides was carried out by direct amidation of fatty acids with alkanolamines. Several fatty acids and alkanolamines were used as starting materials to investigate the effect of the chain length, the presence of C=C bond, and the number of hydroxyl group of alkanolamides on the cytotoxic activity against HeLa cell line and also antimicrobial activity against Escherichia coli and Staphylococcus aureus. The structure of synthesized alkanolamides was characterized using FTIR and 1H-NMR spectroscopy, the cytotoxic activity was evaluated using a standard MTT assay, and the antimicrobial activity was determined using the disc diffusion method. The data showed that all alkanolamides exhibited cytotoxic and antimicrobial activity. A long-saturated alkyl chain was advantageous for the activities. Alkanolamide stearate-monoethanolamine showed the highest cytotoxic activity (IC50 = 37.5 M) and antimicrobial activity. The presence of C=C bond decreased the activities. However, the polyunsaturated alkyl chain expressed greater activities than the monounsaturated alkyl chain. The number of hydroxyl groups on alkanolamines residue indicated a small contribution to the activity. Therefore, fatty alkanolamide is promising to be developed as an anti-cancer and antimicrobial drug.

DOI

10.21608/ejchem.2023.212786.8007

Keywords

Fatty alkanolamide, direct amidation, Cytotoxic activity, antimicrobial activity, lipoamide

Authors

First Name

Tuti

Last Name

Wukirsari

MiddleName

-

Affiliation

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, Indonesia

Email

tutiwukirsari@sci.ui.ac.id

City

-

Orcid

0000-0002-8457-5578

First Name

Nadiroh

Last Name

Nadiroh

MiddleName

-

Affiliation

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, Indonesia

Email

nadiroh81@ui.ac.id

City

-

Orcid

0000-0001-9219-6861

First Name

Tiara

Last Name

Kembara

MiddleName

F

Affiliation

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, Indonesia

Email

tiara.franscisca@ui.ac.id

City

-

Orcid

0000-0003-4509-7814

First Name

Muhamad

Last Name

Gunawan

MiddleName

Irsyad A.

Affiliation

Department of Chemistry, Faculty of Matematics and Natural Sciences, Universitas Indonesia, Depok, Indonesia

Email

muhamad.irsyad@ui.ac.id

City

-

Orcid

0000-0003-2174-0895

First Name

Bambang

Last Name

Priosoeryanto

MiddleName

Pontjo

Affiliation

School of Veterinary Medicine and Biomedicine, IPB University, Bogor, Indonesia

Email

bpontjo@apps.ipb.ac.id

City

-

Orcid

0000-0001-5942-7402

First Name

Sri

Last Name

Handayani

MiddleName

-

Affiliation

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, Indonesia

Email

yani_hartono64@sci.ui.ac.id

City

-

Orcid

0000-0001-5578-8585

First Name

Sumi

Last Name

Hudiyono

MiddleName

-

Affiliation

Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Depok, Indonesia

Email

sumi.hudiyono@sci.ui.ac.id

City

-

Orcid

-

Volume

67

Article Issue

9

Related Issue

48208

Issue Date

2024-09-01

Receive Date

2023-05-23

Publish Date

2024-09-01

Page Start

289

Page End

295

Print ISSN

0449-2285

Online ISSN

2357-0245

Article File

EJCHEM_Volume 67_Issue 9_Pages 289-295.pdf

PDF . 510.0kB

Link

https://ejchem.journals.ekb.eg/article_312100.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=312100

Order

312,100

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

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

MainTitle

The Effect of Fatty Alkanolamide Structure on Cytotoxic and Antimicrobial Activity

Details

Type

Article

Created At

30 Dec 2024