Antiproliferative evaluations of triazoloquinazolines as classical DNA intercalators: Design, synthesis, ADMET profile, and molecular docking.
Antineoplastic Agents
Cell Line, Tumor
Cell Proliferation
DNA
/ chemistry
Dose-Response Relationship, Drug
Doxorubicin
/ pharmacology
Drug Design
Drug Screening Assays, Antitumor
Humans
Intercalating Agents
/ pharmacology
Molecular Docking Simulation
Molecular Structure
Quinazolines
Structure-Activity Relationship
Triazoles
DNA intercalators
[1,2,4]triazolo[4,3-c]quinazoline
anticancer agents
molecular docking
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
May 2022
May 2022
Historique:
revised:
26
01
2022
received:
09
12
2021
accepted:
28
01
2022
pubmed:
24
2
2022
medline:
4
5
2022
entrez:
23
2
2022
Statut:
ppublish
Résumé
Novel triazoloquinazolines were designed and synthesized and evaluated as anticancer agents against HepG2 and HCT-116 cells. The biological testing data corresponded well to those of the molecular docking studies. The HCT-116 cell line was most affected due to the actions of our derivatives. Derivative 7
Identifiants
pubmed: 35194810
doi: 10.1002/ardp.202100487
doi:
Substances chimiques
Antineoplastic Agents
0
Intercalating Agents
0
Quinazolines
0
Triazoles
0
triazoloquinazoline
0
Doxorubicin
80168379AG
DNA
9007-49-2
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2100487Subventions
Organisme : None
Informations de copyright
© 2022 Deutsche Pharmazeutische Gesellschaft.
Références
G. Marzaro, L. Dalla Via, A. Toninello, A. Guiotto, A. Chilin, Bioorg. Med. Chem. 2011, 19, 1197. https://doi.org/10.1016/j.bmc.2010.12.037
E. B. Skibo, X. Huang, R. Martinez, R. H. Lemus, W. A. Craigo, R. T. Dorr, J. Med. Chem. 2002, 45, 5543. https://doi.org/10.1021/jm020285l
Z. Ma, Y. Hano, T. Nomura, Y. Chen, Bioorg. Med. Chem. Lett. 2004, 14, 1193.
H. J. Park, Y.-S. Kim, J. S. Kim, E.-J. Lee, Y.-J. Yi, H. J. Hwang, M.-E. Suh, C.-K. Ryu, S. K. Lee, Bioorg. Med. Chem. Lett. 2004, 14, 3385.
B. Oyallon, M. Brachet-Botineau, C. Logé, P. Bonnet, M. Souab, T. Robert, S. Ruchaud, S. Bach, P. Berthelot, F. Gouilleux, Eur. J. Med. Chem. 2018, 154, 101.
A. Garofalo, L. Goossens, B. Baldeyrou, A. Lemoine, S. Ravez, P. Six, M.-H. David-Cordonnier, J.-P. Bonte, P. Depreux, A. Lansiaux, J.-F. Goossens, J. Med. Chem. 2010, 53(22), 8089. https://doi.org/10.1021/jm1009605
D. Kaneko, M. Ninomiya, R. Yoshikawa, Y. Ono, A. D. Sonawane, K. Tanaka, A. Nishina, M. Koketsu, Bioorg. Chem. 2020, 104, 104293, https://doi.org/10.1016/j.bioorg.2020.104293
A. A. El-Helby, R. R. A. Ayyad, H. Sakr, K. El-Adl, M. M. Ali, F. Khedr, Arch. Pharm. (Weinheim) 2017, 350(12), 1. https://doi.org/10.1002/ardp.201700240
K. El-Adl, H. Sakr, M. Nasser, F. M. A. Shoman, Arch. Pharm. 2020, 353, e2000079. https://doi.org/10.1002/ardp.202000079
K. El-Adl, A. A. El-Helby, H. Sakr, S. S. A. El-Hddad, Arch. Pharm. 2020, 353, e2000068. https://doi.org/10.1002/ardp.202000068
K. El-Adl, A. A. El-Helby, H. Sakr, I. H. Eissa, S. S. A. El-Hddad, F. M. A. Shoman, Bioorg. Chem. 2020, 102, 104059, https://doi.org/10.1016/j.bioorg.2020.104059
A. M. Sayed, F. A. Taher, M. R. K. Abdel-Samad, M. S. A. El-Gaby, K. El-Adl, N. M. Saleh, Bioorg. Chem. 2021, 108, 104669. Epub January 21, 2021. https://doi.org/10.1016/j.bioorg.2021.104669
M. H. El-Shershaby, A. Ghiaty, A. H. Bayoumi, H. E. A. Ahmed, M. S. El-Zoghbi, K. El-Adl, H. S. Abulkhair, New J. Chem. 2021, 45, 11136. https://doi.org/10.1039/D1NJ00710F
A. A. El-Helby, H. Sakr, R. R. A. Ayyad, K. El-Adl, M. M. Ali, F. Khedr, Anticancer Agents Med Chem, 2018, 18(8), 1184.
N. M. Saleh, A. A.-H. Abdel-Rahman, A. M. Omar, M. M. Khalifa, K. El-Adl, Arch. Pharm. 2021, 354, e2100085. https://doi.org/10.1002/ardp.202100085
F. Khedr, M.-K. Ibrahim, I. H. Eissa, H. S. Abulkhair, K. El-Adl, Arch. Pharm. 2021, 354, e2100201. https://doi.org/10.1002/ardp.202100201
K. El-Adl, M.-K. Ibrahim, F. Khedr, H. S. Abulkhair, I. H. Eissa, Arch. Pharm. 2021, 355, e2100278. https://doi.org/10.1002/ardp.202100278
K. El-Adl, M.-K. Ibrahim, F. Khedr, H. S. Abulkhair, I. H. Eissa, Arch. Pharm. 2020, 354, e2000219. https://doi.org/10.1002/ardp.202000219
M. A. El-Zahabi, H. Sakr, K. El-Adl, M. Zayed, A. S. Abdelraheem, S. I. Eissa, H. Elkady, I. H. Eissa, Bioorg. Chem. 2020, 104, 104218. https://doi.org/10.1016/j.bioorg.2020.104218
N. E. A. Abd El-Sattar, K. El-Adl, M. A. El-Hashash, S. A. Salama, M. M. Elhady, Bioorg. Chem. 2021, 115, 105186. https://doi.org/10.1016/j.bioorg.2021.105186
K. El-Adl, H. M. Sakr, R. G. Yousef, A. B. M. Mehany, A. M. Metwaly, M. A. Elhendawy, M. M. Radwan, M. A. ElSohly, H. S. Abulkhair, I. H. Eissa, Bioorg. Chem. 2021, 114, 114, https://doi.org/10.1016/j.bioorg.2021.105105
N. M. Saleh, M. S. A. El-Gaby, K. El-Adl, N. E. A. Abd El-Sattar, Bioorg. Chem. 2020, 104, 104350, https://doi.org/10.1016/j.bioorg.2020.104350
K. El-Adl, M.-K. Ibrahim, M. S. Alesawy, I. H. Eissa, Bioorg. Med. Chem. 2021, 30, 115958. https://doi.org/10.1016/j.bmc.2020.115958
K. El-Adl, A. A. El-Helby, H. Sakr, A. Elwan, Bioorg. Chem. 2020, 105, 104399. https://doi.org/10.1016/j.bioorg.2020.104399
K. El-Adl, A. A. El-Helby, H. Sakr, A. Elwan, New J. Chem. 2021, 45, 881. https://doi.org/10.1039/D0NJ02990D
M. S. Alesawy, M.-K. Ibrahim, I. H. Eissa, K. El-Adl, Arch. Pharm. 2022, e2100412. https://doi.org/10.1002/ardp.202100412
M. F. Braña, M. Cacho, A. Gradillas, B. de Pascual-Teresa, A. Ramos, Curr. Pharm. Des. 2001, 7(17), 1745. https://doi.org/10.2174/1381612013397113.
D. E. Graves, L. M. Velea, Curr. Org. Chem. 2000, 4, 915.
M. K. Goftar, N. M. Kor, Z. M. Kor, Int. J. Adv. Biol. Biomed. Res. 2014, 2(3), 811.
L. Strekowski, B. Wilson, Mutat. Res. 2007, 623(1-2), 3.
A. Paul, S. Bhattacharya, Curr. Sci. 2012, 102, 212.
M. Sirajuddin, S. Ali, A. Badshah, J. Photochem. Photobiol. B. 2013, 124, 1, https://doi.org/10.1016/j.jphotobiol.2013.03.013
F. Gago, Methods, 1998, 14, 277.
C. Avendano, J. Menéndez, Medicinal Chemistry of Anticancer Drugs, 2nd ed., Elsevier 2008, p. 199.
G. Minotti, P. Menna, E. Salvatorelli, G. Cairo, L. Gianni, Pharmacol. Rev. 2004, 56, 185.
J. Gallego, A. R. Ortiz, B. de Pascual-Teresa, F. Gago, J. Comput.-Aided Mol. Des. 1997, 11, 114.
A. Soni, P. Khurana, T. Singh, B. Jayaram, Bioinformatics, 2017, 33(10), 1488. https://doi.org/10.1093/bioinformatics/btx006
S. Takenaka, M. Takagi, Bull. Chem. Soc. Jpn. 1999, 72, 327.
L. F. Liu, Annu. Rev. Biochem. 1989, 58, 351.
A. Chilin, G. Marzaro, C. Marzano, L. Dalla Via, M. G. Ferlin, G. Pastorini, A. Guiotto, Bioorg. Med. Chem. 2009, 17, 523.
T. D. Shenkenberg, D. D. Von Hoff, Ann. Intern. Med. 1986, 105, 67.
C. C. Wu, Y. C. Li, Y. R. Wang, T. K. Li, N. L. Chan, Nucleic Acids Res. 2013, 41(22), 10630. https://doi.org/10.1093/nar/gkt828
T. Mosmann, J. Immunol. Methods 1983, 65(1-2), 55.
D.A. Scudiero, R. H. Shoemaker, K. D. Paull, A. Monks, S. Tierney, T. H. Nofziger, M. J. Currens, D. Seniff, M. R. Boyd, Cancer Res. 1988, 48(17), 4827.
F. M. Freimoser, C. A. Jakob, M. Aebi, U. Tuor, Appl. Environ. Microbiol. 1999, 65(8), 3727.
N. S. Burres, A. Frigo, R. R. Rasmussen, J. B. McAlpine, J. Nat. Prod. 1992, 55, 1582.
C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Deliv. Rev. 1997, 23, 3. https://doi.org/10.1016/S0169-409X(96)00423-1
D. E. V. Pires, T. L. Blundell, D. B. Ascher, J. Med. Chem. 2015, 58, 4066. https://doi.org/10.1021/acs.jmedchem.5b00104
A. Beig, R. Agbaria, A. Dahan, PLoS One. 2013, 8, e68237. https://doi.org/10.1371/journal.pone.0068237