Open Access
Synthesis, human topoisomerase IIα inhibitory properties and molecular modeling studies of anti-proliferative curcumin mimics
Nehmedo G Fawzy
1
,
Siva S Panda
2, 3, 4, 5, 6
,
W. Fayad
7
,
Walid Fayad
8, 9, 10, 11, 12
,
ElSayed M Shalaby
10, 12, 13, 14, 15, 16
,
Aladdin M Srour
10, 12, 16, 17, 18
,
Adel S Girgis
1, 10, 12, 16, 19
3
Department of Chemistry & Physics
5
Augusta
|
6
Usa
|
8
Drug Bioassay-Cell Culture Laboratory
9
Pharmacognosy Department
10
National Research Centre
11
Giza
|
12
EGYPT
|
13
14
X-Ray Crystallography Lab.
15
Physics Division
16
Giza 12622
|
18
Department of Therapeutic Chemistry
19
Department of Pesticide Chemistry
Publication type: Journal Article
Publication date: 2019-10-21
scimago Q1
wos Q2
SJR: 0.777
CiteScore: 7.6
Impact factor: 4.6
ISSN: 20462069
PubMed ID:
35528906
General Chemistry
General Chemical Engineering
Abstract
3,5-Bis(arylidene)-N-substituted-4-oxo-piperidine-1-carboxamides 24-51 were synthesized as curcumin mimics in a facile pathway through reaction of 3,5-bis(arylidene)-4-piperidones with the appropriate isocyanate in the presence of triethylamine. The 3E,5E'-stereochemical configuration was conclusively supported by single crystal X-ray studies of compounds 25 and 34. Most of the synthesized piperidinecarboxamides showed high anti-proliferative properties with potency higher than that of 5-fluorouracil (clinically approved drug against colon, breast and skin cancers) through in vitro MTT bio-assay. Some of them revealed anti-proliferative properties at sub-micromolar values (IC50 = 0.56-0.70 μM for compounds 29, 30 and 34-38 against HCT116; and IC50 = 0.64 μM for compound 30 against A431 cell lines) with promising inhibitory properties against human DNA topoisomerase IIα. The safe profile of the anti-proliferative active agents against the RPE1 normal cell line may prove their selectivity towards carcinoma cells. Robust molecular models (2D-QSAR, 3D-pharmacophore) supported the SAR and validated the observed bio-properties.
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19
Total citations:
19
Citations from 2024:
7
(36.84%)
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GOST
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Fawzy N. G. et al. Synthesis, human topoisomerase IIα inhibitory properties and molecular modeling studies of anti-proliferative curcumin mimics // RSC Advances. 2019. Vol. 9. No. 58. pp. 33761-33774.
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Fawzy N. G., Panda S. S., Fayad W., Fayad W., Shalaby E. M., Srour A. M., Girgis A. S. Synthesis, human topoisomerase IIα inhibitory properties and molecular modeling studies of anti-proliferative curcumin mimics // RSC Advances. 2019. Vol. 9. No. 58. pp. 33761-33774.
Cite this
RIS
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TY - JOUR
DO - 10.1039/c9ra05661k
UR - https://xlink.rsc.org/?DOI=C9RA05661K
TI - Synthesis, human topoisomerase IIα inhibitory properties and molecular modeling studies of anti-proliferative curcumin mimics
T2 - RSC Advances
AU - Fawzy, Nehmedo G
AU - Panda, Siva S
AU - Fayad, W.
AU - Fayad, Walid
AU - Shalaby, ElSayed M
AU - Srour, Aladdin M
AU - Girgis, Adel S
PY - 2019
DA - 2019/10/21
PB - Royal Society of Chemistry (RSC)
SP - 33761-33774
IS - 58
VL - 9
PMID - 35528906
SN - 2046-2069
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Fawzy,
author = {Nehmedo G Fawzy and Siva S Panda and W. Fayad and Walid Fayad and ElSayed M Shalaby and Aladdin M Srour and Adel S Girgis},
title = {Synthesis, human topoisomerase IIα inhibitory properties and molecular modeling studies of anti-proliferative curcumin mimics},
journal = {RSC Advances},
year = {2019},
volume = {9},
publisher = {Royal Society of Chemistry (RSC)},
month = {oct},
url = {https://xlink.rsc.org/?DOI=C9RA05661K},
number = {58},
pages = {33761--33774},
doi = {10.1039/c9ra05661k}
}
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MLA
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Fawzy, Nehmedo G., et al. “Synthesis, human topoisomerase IIα inhibitory properties and molecular modeling studies of anti-proliferative curcumin mimics.” RSC Advances, vol. 9, no. 58, Oct. 2019, pp. 33761-33774. https://xlink.rsc.org/?DOI=C9RA05661K.