Synthesis of novel nicotinic acid derivatives of potential antioxidant and anticancer activity.
Humans
Sorafenib
/ pharmacology
Vascular Endothelial Growth Factor Receptor-2
Molecular Structure
Structure-Activity Relationship
Niacin
/ pharmacology
Antioxidants
/ pharmacology
Vascular Endothelial Growth Factor A
/ pharmacology
Protein Kinase Inhibitors
/ pharmacology
Antineoplastic Agents
/ chemistry
Doxorubicin
/ pharmacology
Neoplasms
Superoxide Dismutase
/ metabolism
Molecular Docking Simulation
Cell Proliferation
Drug Screening Assays, Antitumor
Drug Design
VEGFR-2
antioxidant activity
cytotoxic activity
nicotinic acid
synthesis
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
Dec 2023
Dec 2023
Historique:
revised:
10
09
2023
received:
08
05
2023
accepted:
13
09
2023
medline:
4
12
2023
pubmed:
4
10
2023
entrez:
4
10
2023
Statut:
ppublish
Résumé
This study comprises the design and synthesis of novel nicotinic acid-based cytotoxic agents with selective inhibitory efficacy against the vascular endothelial growth factor receptor-2 (VEGFR-2). Screening of novel compounds for cytotoxicity was assessed against 60 human cancer cell lines. The two most active compounds, 5b and 5c, and the reference drugs sorafenib and doxorubicin were investigated against HCT-15, PC-3, and CF-295 cancer cell lines. Compound 5c exhibited the highest cytotoxic potential compared to doxorubicin against the HCT-15 and PC-3 tumor cell lines. Moreover, it exhibited higher cytotoxic potential and selectivity toward the HCT-15 cell panel compared with sorafenib. Compound 5c demonstrated promising VEGFR-2 inhibition (concentration needed to inhibit cell viability by 50%, IC
Identifiants
pubmed: 37792247
doi: 10.1002/ardp.202300250
doi:
Substances chimiques
Sorafenib
9ZOQ3TZI87
Vascular Endothelial Growth Factor Receptor-2
EC 2.7.10.1
Niacin
2679MF687A
Antioxidants
0
Vascular Endothelial Growth Factor A
0
Protein Kinase Inhibitors
0
Antineoplastic Agents
0
Doxorubicin
80168379AG
Superoxide Dismutase
EC 1.15.1.1
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2300250Subventions
Organisme : None
Informations de copyright
© 2023 Deutsche Pharmazeutische Gesellschaft.
Références
A. Jemal, R. Siegel, E. Ward, Y. Hao, J. Xu, T. Murray, M. J. Thun, CA Cancer J. Clin. 2008, 58, 71. https://doi.org/10.3322/CA.2007.0010
R. Twombly, J. Natl. Cancer Inst. 2005, 97, 330. https://doi.org/10.1093/jnci/97.5.330
N. Frączek, I. Bronisz, M. Pietryka, D. Kępińska, P. Strzała, K. Mielnicka, A. Korga, J. Dudka, J. Chemother. 2016, 28, 457. https://doi.org/10.1080/1120009X.2016.1218158
P. Traxler, P. Furet, Pharmacol. Ther. 1999, 82, 195. https://doi.org/10.1016/S0163-7258(98)00044-8
H. Chen, J. Kovar, S. Sissons, K. Cox, W. Matter, F. Chadwell, P. Luan, C. J. Vlahos, A. Schutz-Geschwender, D. M. Olive, Anal. Biochem. 2005, 338, 136. https://doi.org/10.1016/j.ab.2004.11.015
A. Seeber, E. Gunsilius, G. Gastl, A. Pircher, Oncol. Res. Treat. 2018, 41, 188. https://doi.org/10.1159/000488301
R. J. Arai, V. Petry, P. M. Hoff, M. S. Mano, Biomark. Res. 2018, 6, 20. https://doi.org/10.1186/s40364-018-0135-x
R. K. Jain, E. Di Tomaso, D. G. Duda, J. S. Loeffler, A. G. Sorensen, T. T. Batchelor, Nat. Rev. Neurosci. 2007, 8, 610. https://doi.org/10.1038/nrn2175
S. J. Modi, V. M. Kulkarni, Med. Drug Discov. 2019, 2, 100009. https://doi.org/10.1016/j.medidd.2019.100009
N. M. Saleh, A. A. H. Abdel-Rahman, A. M. Omar, M. M. Khalifa, K. El-Adl, Arch. Pharm.2021, 354, 2100085. https://doi.org/10.1002/ardp.202100085
A. Tandle, S. K. Libutti, Clin. Adv. Hematol. Oncol. 2003, 1, 41.
L. Cao, M. Weetall, J. Bombard, H. Qi, T. Arasu, W. Lennox, J. Hedrick, J. Sheedy, N. Risher, P. C. Brooks, P. Trifillis, C. Trotta, Y. C. Moon, J. Babiak, N. G. Almstead, J. M. Colacino, T. W. Davis, S. W. Peltz, PLoS One 2016, 11. e0168366. https://doi.org/10.1371/journal.pone.0168366
A. C. Dar, K. M. Shokat, Annu. Rev. Biochem. 2011, 80, 769. https://doi.org/10.1146/annurev-biochem-090308-173656
Y. Liu, N. S. Gray, Nat. Chem. Biol. 2006, 2, 358. https://doi.org/10.1038/nchembio799
E. L. Kwak, R. Sordella, D. W. Bell, N. Godin-Heymann, R. A. Okimoto, B. W. Brannigan, P. L. Harris, D. R. Driscoll, P. Fidias, T. J. Lynch, S. K. Rabindran, J. P. McGinnis, A. Wissner, S. V. Sharma, K. J. Isselbacher, J. Settleman, D. A. Haber, Proc. Natl. Acad. Sci. USA2005, 102, 7665. https://doi.org/10.1073/pnas.0502860102
S. Cai, H. Deng, Y. Chen, X. Wu, X. Guan, Medicine 2017, 96. e8704. https://doi.org/10.1097/MD.0000000000008704
J. N. Ho, S. S. Byun, S. Lee, J. I. Youn, S. Lee, Oncol. Rep. 2019, 41, 2482. https://doi.org/10.3892/or.2019.7005
T. Ahmad, T. Eisen, Clin. Cancer Res. 2004, 10, 6388S. https://doi.org/10.1158/1078-0432.CCR-040028
R. G. Yousef, A. Ibrahim, M. M. Khalifa, W. M. Eldehna, I. Gobaara, A. Mehany, E. B. Elkaeed, A. A. Alsfouk, A. M. Metwaly, I. H. Eissa, J. Enzyme Inhib. Med. Chem. 2022, 37, 1389. https://doi.org/10.1080/14756366.2022.2070744
R. G. Yousef, A. Elwan, I. M. M. Gobaara, A. B. M. Mehany, W. M. Eldehna, S. A. El-Metwally, B. A. Alsfouk, E. B. Elkaeed, A. M. Metwaly, I. H. Eissa., J. Enzyme Inhib. Med. Chem. 2022, 37, 2206. https://doi.org/10.1080/14756366.2022.2110868
R. G. Yousef, W. M. Eldehna, A. Elwan, A. S. Abdelaziz, A. B. M. Mehany, I. M. M. Gobaara, B. A. Alsfouk, E. B. Elkaeed, A. M. Metwaly, I. H. Eissa, Molecules 2022, 27, 4079. https://doi.org/10.3390/molecules27134079
E. B. Elkaeed, R. G. Yousef, M. M. Khalifa, A. Ibrahim, A. B. M. Mehany, I. M. M. Gobaara, B. A. Alsfouk, W. M. Eldehna, A. M. Metwaly, I. H. Eissa, M. A. El-Zahabi, Molecules 2022, 27, 6203. https://doi.org/10.3390/molecules27196203
V. A. Machado, D. Peixoto, R. Costa, H. J. C. Froufe, R. C. Calhelha, R. M. V. Abreu, I. C. F. R. Ferreira, R. Soares, M. J. R. P. Queiroz, Bioorg. Med. Chem. 2015, 23, 6497. https://doi.org/10.1016/j.bmc.2015.08.010
J. Dietrich, C. Hulme, L. H. Hurley, Bioorg. Med. Chem. 2010, 18, 5738. https://doi.org/10.1016/j.bmc.2010.05.063
Y. El-Dash, E. Elzayat, A. M. Abdou, R. A. Hassan, Bioorg. Chem. 2021, 114, 105137. https://doi.org/10.1016/j.bioorg.2021.105137
A. Garofalo, L. Goossens, P. Six, A. Lemoine, S. Ravez, A. Farce, P. Depreux, Bioorg. Med. Chem. Lett. 2011, 21, 2106. https://doi.org/10.1016/j.bmcl.2011.01.137
M. A. Aziz, R.A. T. Serya, D. S. Lasheen, A. K. Abdel-Aziz, A. Esmat, A. M. Mansour, A. N. B. Singab, K. A. M. Abouzid, Sci. Rep. 2016, 6, 24460. https://doi.org/10.1038/srep24460
V. G. Klein, A. G. Bond, C. Craigon, R. S. Lokey, A. Ciulli, J. Med. Chem. 2021, 64, 18082. https://doi.org/10.1021/acs.jmedchem.1c01496
O. I. Aruoma, J. Am. Oil Chem. Soc. 1998, 75, 199. https://doi.org/10.1007/s11746-998-0032-9
V. B. Djordjevic, Int. Rev. Cytol. 2004, 237, 57. https://doi.org/10.1016/s0074-7696(04)37002-6
A. T. Dinkova-Kostova, P. Talalay, Mol. Nutr. Food Res. 2008, 52, S128. https://doi.org/10.1002/mnfr.200700195
E. Birben, U. M. Sahiner, C. Sackesen, S. Erzurum, O. Kalayci, World Allergy Organ. J. 2012, 5, 9. https://doi.org/10.1097/wox.0b013e3182439613
B. N. Ames, M. K. Shigenaga, T. M. Hagen, Proc. Natl. Acad. Sci. USA 1993, 90, 7915. https://doi.org/10.1073/pnas.90.17.7915
N. Mut-Salud, P. J. Álvarez, J. M. Garrido, E. Carrasco, A. Aránega, F. Rodríguez-Serrano, Oxid. Med. Cell. Longev. 2016, 2016, 1. https://doi.org/10.1155/2016/6719534
U. Neelamegam, R. Muthuvel, V. Suganthi, J. Pharm. Negat. 2022, 13, 921. https://doi.org/10.47750/pnr.2022.13.S09.110
H. I. Ghamry, Toxics 2023, 11, 107. https://doi.org/10.3390/toxics11020107
K. Singh, M. Bhori, Y. A. Kasu, G. Bhat, T. Marar, Saudi Pharm. J.2018, 26, 177. https://doi.org/10.1016/j.jsps.2017.12.013
I. I. C. Chio, D. A. Tuveson, Trends Mol. Med. 2017, 23, 411. https://doi.org/10.1016/j.molmed.2017.03.004
I. Isnaini, N. Permatasari, K. Mintaroem, B. Prihartini, M. A. Widodo, Asian Pac. J. Cancer Prev. 2018, 19, 3175. https://doi.org/10.31557/APJCP.2018.19.11.3175
H. Younus, Int. J. Health Sci. 2018, 12, 88.
Y. El-Dash, N. A. Khalil, E. M. Ahmed, M. S. A. Hassan, Bioorg. Chem. 2021, 107, 104610. https://doi.org/10.1016/j.bioorg.2020.104610
National Cancer Institute. Developmental Therapeutics Program. NCI; n.d. https://www.dtp.nci.nih.gov.
M. R. Boyd, K. D. Paull, Drug Dev. Res. 1995, 34, 91. https://doi.org/10.1002/ddr.430340203
R. H. Shoemaker, Nat. Rev. Cancer 2006, 6, 813. https://doi.org/10.1038/nrc1951
P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney, M. R. Boyd, J. Natl. Cancer Inst. 1990, 82, 1107. https://doi.org/10.1093/jnci/82.13.1107
T. Mosmann, J. Immunol. Methods 1983, 65, 55. https://doi.org/10.1016/0022-1759(83)90303-4
E. A. Sobh, N. A. Khalil, S. I. Faggal, M. S. A. Hassan, Drug Dev. Res. 2022, 83, 1075. https://doi.org/10.1002/ddr.21934
J. A. Hickman, Cancer Metastasis Rev. 1992, 11, 121. https://doi.org/10.1007/BF00048059
P. Theofilas, A. J. Ambrose, D. Butler, C. Wang, D. O. Morales, C. Petersen, B. Chin, T. Yang, S. Khan, R. Ng, R. Kayed, C. M. Karch, B. L. Miller, J. E. Gestwicki, L. Gan, S. Temple, M. R. Arkin, L. T. Grinberg, Alzheimer's Dement.2021, 17. e051471. https://doi.org/10.1002/alz.051471
J. Zhao, Y. Ming, Q. Wan, S. Ye, S. Xie, Y. Zhu, Y. Wang, Z. Zhong, L. Li, Q. Ye, Exp. Ther. Med. 2014, 7, 1388. https://doi.org/10.3892/etm.2014.1569
P. Yadav, R. Yadav, S. Jain, A. Vaidya, Chem. Biol. Drug Des. 2021, 98, 144. https://doi.org/10.1111/cbdd.13860
C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Deliv. Rev. 2012, 64, 4. https://doi.org/10.1016/S0169-409X(96)00423-1
D. F. Veber, S. R. Johnson, H.-Y. Cheng, B. R. Smith, K. W. Ward, K. D. Kopple, J. Med. Chem. 2002, 45, 2615. https://doi.org/10.1021/jm020017n
J. B. Baell, G. A. Holloway, J. Med. Chem. 2010, 53, 2719. https://doi.org/10.1021/jm901137j
E. Barim, F. Akman, J. Mol. Struct. 2019, 1195, 506. https://doi.org/10.1016/j.molstruc.2019.06.015
G. Bitencourt-Ferreira, W. F. de Azevedo Junior, Curr. Med. Chem. 2021, 28, 4954. https://doi.org/10.2174/0929867328666210201150842
M. C. Alley, D. A. Scudiero, A. Monks, M. L. Hursey, M. J. Czerwinski, D. L. Fine, B. J. Abbott, J. G. Mayo, R. H. Shoemaker, M. R. Boyd, Cancer Res. 1988, 48, 589 PMID: 3335022.
M. F. Tolba, A. Esmat, A. M. Al-Abd, S. S. Azab, A. E. Khalifa, H. A. Mosli, S. Z. Abdel-Rahman, A. B. Abdel-Naim, IUBMB Life 2013, 65, 716. https://doi.org/10.1002/iub.1188
M. Nishikimi, N. Appaji Rao, K. Yagi, Biochem. Biophys. Res. Commun. 1972, 46, 849. https://doi.org/10.1016/S0006-291X(72)80218-3
M. M. Alanazi, H. Elkady, N. A. Alsaif, A. J. Obaidullah, H. M. Alkahtani, M. M. Alanazi, M. A. Alharbi, I. H. Eissa, M. A. Dahab, RSC Adv. 2021, 11, 30315. https://doi.org/10.1039/D1RA05925D
E. B. Elkaeed, R. G. Yousef, H. Elkady, I. Gobaara, B. A. Alsfouk, D. Z. Husein, I. M. Ibrahim, A. M. Metwaly, I. H. Eissa, Molecules 2022, 27, 4606. https://doi.org/10.3390/molecules27144606