Design, synthesis, characterization and cytotoxic activity of new ortho-hydroxy and indole-chalcone derivatives against breast cancer cells (MCF-7)
Twenty-seven new ortho-hydroxy chalcone and a series of indole-chalcone derivatives have been designed and synthesized. The structures of all newly-synthesized compounds were characterized by different spectroscopic techniques and the interactions with tubulin were evaluated for antiproliferative ac...
Saved in:
Main Authors: | , , , , , , |
---|---|
Format: | Article |
Published: |
Springer Verlag
2022
|
Subjects: | |
Online Access: | http://eprints.um.edu.my/33356/ |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
id |
my.um.eprints.33356 |
---|---|
record_format |
eprints |
spelling |
my.um.eprints.333562022-08-08T01:18:45Z http://eprints.um.edu.my/33356/ Design, synthesis, characterization and cytotoxic activity of new ortho-hydroxy and indole-chalcone derivatives against breast cancer cells (MCF-7) Jumaah, Maadh Khairuddean, Melati Owaid, Sohaib Jumaah Zakaria, Nurhisyam Mohd Arshad, Norhafiza Nagoor, Noor Hasima Taib, Mohamad Nurul Azmi Mohamad RM Therapeutics. Pharmacology RS Pharmacy and materia medica Twenty-seven new ortho-hydroxy chalcone and a series of indole-chalcone derivatives have been designed and synthesized. The structures of all newly-synthesized compounds were characterized by different spectroscopic techniques and the interactions with tubulin were evaluated for antiproliferative activities in vitro. The structure-activity relationships were elucidated for compounds with various substituents on the benzene ring of the aldehyde moiety at positions C-3, C-4 and C-5 with constant o-OH. The best inhibition results of ring bioisoterism for cancer cell growth were obtained for compounds 4c, 5j, and 6a with substituents m-tBu, Br and p-OCH3, respectively. Their antiproliferative activity was evaluated in MCF-7 cells, with compound 5j showing cytotoxicity activity comparable to that of reference compound paclitaxel. A computational study was carried out, for calculation of pharmacophore pattern, prediction of pharmacokinetic properties and toxicity. The results of the target compounds are followed by docking studies that have provided structural recommendations for designing new antiproliferative chalcones. GRAPHICS] . Springer Verlag 2022-03 Article PeerReviewed Jumaah, Maadh and Khairuddean, Melati and Owaid, Sohaib Jumaah and Zakaria, Nurhisyam and Mohd Arshad, Norhafiza and Nagoor, Noor Hasima and Taib, Mohamad Nurul Azmi Mohamad (2022) Design, synthesis, characterization and cytotoxic activity of new ortho-hydroxy and indole-chalcone derivatives against breast cancer cells (MCF-7). Medicinal Chemistry Research, 31 (3). pp. 517-532. ISSN 1054-2523, DOI https://doi.org/10.1007/s00044-021-02834-2 <https://doi.org/10.1007/s00044-021-02834-2>. 10.1007/s00044-021-02834-2 |
institution |
Universiti Malaya |
building |
UM Library |
collection |
Institutional Repository |
continent |
Asia |
country |
Malaysia |
content_provider |
Universiti Malaya |
content_source |
UM Research Repository |
url_provider |
http://eprints.um.edu.my/ |
topic |
RM Therapeutics. Pharmacology RS Pharmacy and materia medica |
spellingShingle |
RM Therapeutics. Pharmacology RS Pharmacy and materia medica Jumaah, Maadh Khairuddean, Melati Owaid, Sohaib Jumaah Zakaria, Nurhisyam Mohd Arshad, Norhafiza Nagoor, Noor Hasima Taib, Mohamad Nurul Azmi Mohamad Design, synthesis, characterization and cytotoxic activity of new ortho-hydroxy and indole-chalcone derivatives against breast cancer cells (MCF-7) |
description |
Twenty-seven new ortho-hydroxy chalcone and a series of indole-chalcone derivatives have been designed and synthesized. The structures of all newly-synthesized compounds were characterized by different spectroscopic techniques and the interactions with tubulin were evaluated for antiproliferative activities in vitro. The structure-activity relationships were elucidated for compounds with various substituents on the benzene ring of the aldehyde moiety at positions C-3, C-4 and C-5 with constant o-OH. The best inhibition results of ring bioisoterism for cancer cell growth were obtained for compounds 4c, 5j, and 6a with substituents m-tBu, Br and p-OCH3, respectively. Their antiproliferative activity was evaluated in MCF-7 cells, with compound 5j showing cytotoxicity activity comparable to that of reference compound paclitaxel. A computational study was carried out, for calculation of pharmacophore pattern, prediction of pharmacokinetic properties and toxicity. The results of the target compounds are followed by docking studies that have provided structural recommendations for designing new antiproliferative chalcones. GRAPHICS] . |
format |
Article |
author |
Jumaah, Maadh Khairuddean, Melati Owaid, Sohaib Jumaah Zakaria, Nurhisyam Mohd Arshad, Norhafiza Nagoor, Noor Hasima Taib, Mohamad Nurul Azmi Mohamad |
author_facet |
Jumaah, Maadh Khairuddean, Melati Owaid, Sohaib Jumaah Zakaria, Nurhisyam Mohd Arshad, Norhafiza Nagoor, Noor Hasima Taib, Mohamad Nurul Azmi Mohamad |
author_sort |
Jumaah, Maadh |
title |
Design, synthesis, characterization and cytotoxic activity of new ortho-hydroxy and indole-chalcone derivatives against breast cancer cells (MCF-7) |
title_short |
Design, synthesis, characterization and cytotoxic activity of new ortho-hydroxy and indole-chalcone derivatives against breast cancer cells (MCF-7) |
title_full |
Design, synthesis, characterization and cytotoxic activity of new ortho-hydroxy and indole-chalcone derivatives against breast cancer cells (MCF-7) |
title_fullStr |
Design, synthesis, characterization and cytotoxic activity of new ortho-hydroxy and indole-chalcone derivatives against breast cancer cells (MCF-7) |
title_full_unstemmed |
Design, synthesis, characterization and cytotoxic activity of new ortho-hydroxy and indole-chalcone derivatives against breast cancer cells (MCF-7) |
title_sort |
design, synthesis, characterization and cytotoxic activity of new ortho-hydroxy and indole-chalcone derivatives against breast cancer cells (mcf-7) |
publisher |
Springer Verlag |
publishDate |
2022 |
url |
http://eprints.um.edu.my/33356/ |
_version_ |
1740826024432631808 |
score |
13.18916 |