Synthesis and biological evaluation of novel salicylidene uracils: Cytotoxic activity on human cancer cell lines and inhibitory action on enzymatic activity.
carbonic anhydrase
cholinesterases
cytotoxicity
glutathione reductase
salicylidene uracil
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
30 Oct 2023
30 Oct 2023
Historique:
revised:
12
10
2023
received:
11
07
2023
accepted:
14
10
2023
medline:
30
10
2023
pubmed:
30
10
2023
entrez:
30
10
2023
Statut:
aheadofprint
Résumé
A series of salicylidene uracil (1-18) derived from 5-aminouracil and substituted salicylaldehydes were analyzed for cytotoxic activity and enzyme inhibitory potency. Nine out of eighteen derivatives (6-8, 10, 12-15, 18) are novel molecules synthesized for the first time in this work, and other derivatives were previously synthesized by our group. The compounds were characterized by Proton nuclear magnetic resonance, carbon nuclear magnetic resonance, fourier transform infrared spectroscopy, and elemental analysis. All compounds were tested for their in vitro cytotoxicity against PC-3 (human prostate adenocarcinoma), A549 (human alveolar adenocarcinoma), and SHSY-5Y (human neuroblastoma) cancer cell lines and the nontumorigenic HEK293 (human embryonic kidney cells) cell line. The 3,5-di-tert-butylsalicylaldehyde derived compound (8) was toxic to PC-3 human prostate adenocarcinoma cells, showing a promising IC
Identifiants
pubmed: 37902389
doi: 10.1002/ardp.202300374
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2300374Subventions
Organisme : Türkiye Bilimsel ve Teknolojik Arastirma Kurumu
Organisme : Scientific and Technological Research Council of Turkey
ID : 217Z221
Organisme : Bursa Technical University Scientific Research Fund
ID : 182L14
Informations de copyright
© 2023 The Authors. Archiv der Pharmazie published by Wiley-VCH GmbH on behalf of Deutsche Pharmazeutische Gesellschaft.
Références
T. Pathak, Chem. Rev. 2002, 102, 1623.
D. Ramesh, B. G. Vijayakumar, T. Kannan, Eur. J. Med. Chem. 2020, 207, 112801.
A. Pałasz, D. Cież, Eur. J. Med. Chem. 2015, 97, 582.
N. A. Illán-Cabeza, A. R. García-García, J. M. Martínez-Martos, M. J. Ramírez-Expósito, T. Peña-Ruiz, M. N. Moreno-Carretero, Eur. J. Med. Chem. 2013, 64, 260.
W. B. Parker, Chem. Rev. 2009, 109, 2880.
D. A. Babkov, A. L. Khandazhinskaya, A. O. Chizhov, G. Andrei, R. Snoeck, K. L. Seley-Radtke, M. S. Novikov, Bioorg. Med. Chem. 2015, 23, 7035.
D.-Z. Li, Q.-Z. Zhang, C.-Y. Wang, Y.-L. Zhang, X.-Y. Li, J.-T. Huang, H.-Y. Liu, Z.-D. Fu, H.-X. Song, J.-P. Lin, T.-F. Ji, X.-D. Pan, Eur. J. Med. Chem. 2017, 125, 1235.
M. Sanduja, J. Gupta, T. Virmani, J. Appl. Pharm. Sci. 2020, 10(02), 129.
M. Guney, H. Cavdar, M. Senturk, D. Ekinci, Bioorg. Med. Chem. Lett. 2015, 25(16), 3261.
E. A. Turkoglu, M. Senturk, C. T. Supuran, D. Ekinci, J. Enzym. Inhib. Med. Chem. 2017, 32(1), 74.
M. Guney, D. Ekinci, H. Cavdar, M. Senturk, K. Zilbeyaz, AIP Conf. Proc. 2016, 1726(1), 020104.
H. Cavdar, M. Senturk, M. Guney, S. Durdagi, G. Kayik, C. T. Supuran, D. Ekinci, J. Enzyme Inhib. Med. Chem. 2019, 34(1), 429.
Z. Bulut, N. Abul, A. H. Poslu, I. Gülçin, A. Ece, E. Erçağ, Ö. Koz, G. Koz, J. Mol. Struct. 2023, 1280, 135047.
S. Durdagi, M. Şentürk, D. Ekinci, H. T. Balaydın, S. Göksu, Ö. İ. Küfrevioğlu, A. Innocenti, A. Scozzafava, C. T. Supuran, Bioorg. Med. Chem. 2011, 19(4), 1381.
H. Cavdar, D. Ekinci, O. Talaz, N. Saracoglu, M. Senturk, C. T. Supuran, J. Enzym. Inhib. Med. Chem. 2012, 27(1), 148.
D. Ekinci, H. Çavdar, S. Durdagi, O. Talaz, M. Şentürk, C. T. Supuran, Eur. J. Med. Chem. 2012, 49, 68.
H. T. Balaydin, M. Senturk, A. Menzek, Bioorg. Med. Chem. Lett. 2012, 22, 1352.
S. Isık, D. Vullo, S. Durdagi, D. Ekinci, M. Senturk, A. Cetin, E. Senturk, C. T. Supuran, Bioorg. Med. Chem. Lett. 2015, 25(23), 5636.
K. K. Upadhyay, A. Kumar, Org. Biomol. Chem. 2010, 8, 4892.
N. A. Illán-Cabeza, R. A. Vilaplana, Y. Alvarez, K. Akdi, S. Kamah, F. Hueso-Ureña, M. Quirós, F. González-Vílchez, M. N. Moreno-Carretero, JBIC, J. Biol. Inorg. Chem. 2005, 10, 924.
H. H. Hammud, S. El Shazly, G. Sonji, N. Sonji, K. H. Bouhadir, Spectrochim. Acta A Mol. Biomol. Spectrosc. 2015, 150, 94.
N. A. Illán-Cabeza, S. B. Jiménez-Pulido, F. Hueso-Ureña, M. J. Ramírez-Expósito, P. Sánchez-Sánchez, J. M. Martínez-Martos, M. N. Moreno-Carretero, J. Inorg. Biochem. 2018, 185, 52.
N. A. Illán-Cabeza, S. B. Jiménez-Pulido, F. Hueso-Ureña, M. J. Ramírez-Expósito, J. M. Martínez-Martos, M. N. Moreno-Carretero, J. Inorg. Biochem. 2020, 207, 111053.
S. Maikoo, L. M. K. Dingle, A. Chakraborty, B. Xulu, A. L. Edkins, I. N. Booysen, Polyhedron 2020, 184, 114569.
C. T. Supuran, Nat. Rev. Drug Discov. 2008, 7(2), 168.
R. Yaseen, D. Ekinci, M. Senturk, A. D. Hameed, S. Ovais, P. Rathore, M. Samim, K. Javed, C. T. Supuran, Bioorg. Med. Chem. Lett. 2016, 26(4), 1337.
M. Özil, H. T. Balaydın, M. Şentürk, Bioorg. Chem. 2019, 86, 705.
H. Khan, S. A. Marya, S. Amin, M. A. Kamal, S. Patel, Biomed. Pharmacother. 2018, 101, 860.
M. M. Mesulam, A. Guillozet, P. Shaw, A. Levey, E. G. Duysen, O. Lockridge, Neuroscience 2002, 110(4), 627.
S. I. Zacks, J. M. Blumberg, J. Histochem. Cytochem. 1961, 9, 317.
C. G. Carolan, G. P. Dillon, D. Khan, S. A. Ryder, J. M. Gaynor, S. Reidy, J. F. Marquez, M. Jones, V. Holland, J. F. Gilmer, J. Med. Chem. 2010, 53(3), 1190.
A. Pastore, G. Federici, E. Bertini, F. Piemonte, Clin. Chim. Acta 2003, 333, 19.
C. Perricone, C. De Carolis, R. Perricone, Autoimmun. Rev. 2009, 8, 697.
R. L. Krauth-Siegel, H. Bauer, R. H. Schirmer, Angew. Chem. Int. Ed. Engl. 2005, 44, 690.
C. Biot, H. Bauer, R. H. Schirmer, E. Davioud-Charvet, J. Med. Chem. 2004, 47, 5972.
G. Koz, H. Kaya, D. Astley, I. Yasa, S. T. Astley, GUJ Sci 2011, 24(3), 407.
G. Koz, Russ. J. Gen. Chem. 2019, 89, 122.
Y. Takaoka, Y. Kioi, A. Morito, J. Otani, K. Arita, E. Ashihara, M. Ariyoshi, H. Tochio, M. Shirakawa, I. Hamachi, Chem. Commun. 2013, 49(27), 2801.
V. Dudutienė, J. Matulienė, A. Smirnov, D. D. Timm, A. Zubrienė, L. Baranauskienė, V. Morku̅naitė, J. Smirnovienė, V. Michailovienė, V. Juozapaitienė, A. Mickevičiu̅tė, J. Kazokaitė, S. Bakšytė, A. Kasiliauskaitė, J. Jachno, J. Revuckienė, M. Kišonaitė, V. Pilipuitytė, E. Ivanauskaitė, G. Milinavičiu̅tė, V. Smirnovas, V. Petrikaitė, V. Kairys, V. Petrauskas, P. Norvaišas, D. Lingė, P. Gibieža, E. Čapkauskaitė, A. Zakšauskas, E. Kazlauskas, E. Manakova, S. Gražulis, J. E. Ladbury, D. Matulis, J. Med. Chem. 2014, 57(22), 9435.
J. Cheung, M. J. Rudolph, F. Burshteyn, M. S. Cassidy, E. N. Gary, J. Love, M. C. Franklin, J. J. Height, J. Med. Chem. 2012, 55(22), 10282.
F. Nachon, E. Carletti, C. Ronco, M. Trovaslet, Y. Nicolet, L. Jean, P. Y. Renard, Biochem. J. 2013, 453(3), 393.
D. M. Kasozi, S. Gromer, H. Adler, K. Zocher, S. Rahlfs, S. Wittlin, K. Fritz-Wolf, R. H. Schirmer, K. Becker, Redox Rep. 2011, 16(4), 154.
M. D. Hanwell, D. E. Curtis, D. C. Lonie, T. Vandermeerschd, E. Zurek, G. R. Hutchison, J. Cheminform. 2012, 4(17).
S. Dallakyan, A. J. Olson, Methods Mol. Biol. 2015, 1263, 243.
O. Trott, A. J. Olson, J. Comput. Chem. 2010, 31(2), 455.
G. Koz, Hacettepe J. Biol. & Chem. 2018, 46(3), 373.
T. Mosmann, J. Immunol. Methods 1983, 65, 55.
A. Nalbantsoy, N. Igci, B. Gocmen, K. Mebert, J. Zool. 2016, 12(2), 286.
E. Beutler, R. ed Cell, Metabolism. A manual of biochemical methods, Grune and Stratton Inc, Orlando 1984, pp. 134.
J. A. Verpoorte, S. Mehta, J. T. Edsall, J. Biol. Chem. 1967, 242(18), 4221.
G. L. Ellman, K. D. Courtney, V. Andres Jr., R. M. Feather-Stone, Biochem. Pharmacol. 1961, 7, 88.