Skip to main content

Lund University Publications

LUND UNIVERSITY LIBRARIES

Synthesis, in vitro cytotoxicity activity against the human cervix carcinoma cell line and in silico computational predictions of new 4-arylamino-3-nitrocoumarin analogues

Halawa, Ahmed H. ; Eliwa, Essam M. ; Hassan, Ahmed A. ; Nassar, Hesham S. ; El-Eisawy, R. A. ; Ismail, Mohamed LU orcid ; Frese, Marcel ; Shaaban, Mohamed ; El-Agrody, Ahmed M. and Bedair, Ahmed H. , et al. (2020) In Journal of Molecular Structure 1200.
Abstract

A new series of 4-arylamino-3-nitrocoumarin analogues (4–18) have been synthesized and characterized by sophisticated spectroscopic techniques (1H NMR, 13C NMR) and mass spectrometry. All the new synthesized compounds were evaluated for their in vitro cytotoxic activity against the human cervix carcinoma cell line (KB-3-1) using resazurin assay with (+)-griseofulvin as the positive control (IC50 = 19 μM). Among them, thiazolidinylidene derivative 17a that bearing malononitrile unit displayed the best cytotoxic potency with IC50 value of 21 μM. Also, in silico docking simulation studies were conducted on human DNA topoisomerase 1 (Top1) (PDB: 1T8I) to explore and interpret the interaction... (More)

A new series of 4-arylamino-3-nitrocoumarin analogues (4–18) have been synthesized and characterized by sophisticated spectroscopic techniques (1H NMR, 13C NMR) and mass spectrometry. All the new synthesized compounds were evaluated for their in vitro cytotoxic activity against the human cervix carcinoma cell line (KB-3-1) using resazurin assay with (+)-griseofulvin as the positive control (IC50 = 19 μM). Among them, thiazolidinylidene derivative 17a that bearing malononitrile unit displayed the best cytotoxic potency with IC50 value of 21 μM. Also, in silico docking simulation studies were conducted on human DNA topoisomerase 1 (Top1) (PDB: 1T8I) to explore and interpret the interaction pattern between the selected compounds and target enzyme as well confirm the acquired cytotoxicity results. In addition to the above, in silico predictions of physicochemical properties, ADME (absorption, distribution, metabolism and excretion) parameters, oral toxicity and indication of toxicity targets were implemented for some title compounds.

(Less)
Please use this url to cite or link to this publication:
author
; ; ; ; ; ; ; ; and , et al. (More)
; ; ; ; ; ; ; ; ; and (Less)
publishing date
type
Contribution to journal
publication status
published
keywords
4-Arylamino-3-nitrocoumarin, Cervical cancer, Cytotoxic activity, In silico computational predictions, Top1-DNA complex
in
Journal of Molecular Structure
volume
1200
article number
127047
publisher
Elsevier
external identifiers
  • scopus:85072201103
ISSN
0022-2860
DOI
10.1016/j.molstruc.2019.127047
language
English
LU publication?
no
id
df35baa9-7d82-452f-98cb-0af3ef7e7373
date added to LUP
2023-08-28 11:47:07
date last changed
2023-10-04 10:06:04
@article{df35baa9-7d82-452f-98cb-0af3ef7e7373,
  abstract     = {{<p>A new series of 4-arylamino-3-nitrocoumarin analogues (4–18) have been synthesized and characterized by sophisticated spectroscopic techniques (<sup>1</sup>H NMR, <sup>13</sup>C NMR) and mass spectrometry. All the new synthesized compounds were evaluated for their in vitro cytotoxic activity against the human cervix carcinoma cell line (KB-3-1) using resazurin assay with (+)-griseofulvin as the positive control (IC<sub>50</sub> = 19 μM). Among them, thiazolidinylidene derivative 17a that bearing malononitrile unit displayed the best cytotoxic potency with IC<sub>50</sub> value of 21 μM. Also, in silico docking simulation studies were conducted on human DNA topoisomerase 1 (Top1) (PDB: 1T8I) to explore and interpret the interaction pattern between the selected compounds and target enzyme as well confirm the acquired cytotoxicity results. In addition to the above, in silico predictions of physicochemical properties, ADME (absorption, distribution, metabolism and excretion) parameters, oral toxicity and indication of toxicity targets were implemented for some title compounds.</p>}},
  author       = {{Halawa, Ahmed H. and Eliwa, Essam M. and Hassan, Ahmed A. and Nassar, Hesham S. and El-Eisawy, R. A. and Ismail, Mohamed and Frese, Marcel and Shaaban, Mohamed and El-Agrody, Ahmed M. and Bedair, Ahmed H. and Sewald, Norbert}},
  issn         = {{0022-2860}},
  keywords     = {{4-Arylamino-3-nitrocoumarin; Cervical cancer; Cytotoxic activity; In silico computational predictions; Top1-DNA complex}},
  language     = {{eng}},
  month        = {{01}},
  publisher    = {{Elsevier}},
  series       = {{Journal of Molecular Structure}},
  title        = {{Synthesis, <i>in vitro</i> cytotoxicity activity against the human cervix carcinoma cell line and <i>in silico</i> computational predictions of new 4-arylamino-3-nitrocoumarin analogues}},
  url          = {{http://dx.doi.org/10.1016/j.molstruc.2019.127047}},
  doi          = {{10.1016/j.molstruc.2019.127047}},
  volume       = {{1200}},
  year         = {{2020}},
}