Verubulin (Azixa) Analogues with Increased Saturation: Synthesis, SAR and Encapsulation in Biocompatible Nanocontainers Based on Ca
apoptosis inducer
aromatic nucleophilic substitution
cross-linked alginate
nanocontainer
pyrimidine
tetrahydroquinazoline
tubulin polymerization inhibitor
verubulin
Journal
Pharmaceuticals (Basel, Switzerland)
ISSN: 1424-8247
Titre abrégé: Pharmaceuticals (Basel)
Pays: Switzerland
ID NLM: 101238453
Informations de publication
Date de publication:
21 Oct 2023
21 Oct 2023
Historique:
received:
14
09
2023
revised:
09
10
2023
accepted:
19
10
2023
medline:
28
10
2023
pubmed:
28
10
2023
entrez:
28
10
2023
Statut:
epublish
Résumé
Tubulin-targeting agents attract undiminished attention as promising compounds for the design of anti-cancer drugs. Verubulin is a potent tubulin polymerization inhibitor, binding to colchicine-binding sites. In the present work, a series of verubulin analogues containing a cyclohexane or cycloheptane ring 1,2-annulated with pyrimidine moiety and various substituents in positions 2 and 4 of pyrimidine were obtained and their cytotoxicity towards cancer and non-cancerous cell lines was estimated. The investigated compounds revealed activity against various cancer cell lines with IC
Identifiants
pubmed: 37895970
pii: ph16101499
doi: 10.3390/ph16101499
pmc: PMC10610134
pii:
doi:
Types de publication
Journal Article
Langues
eng
Subventions
Organisme : Ministry of Science and Higher Education of the Russian Federation
ID : Agreement with Zelinsky Institute of Organic Chemistry RAS No 075-15-2020-803
Organisme : Russian Science Foundation
ID : 22-14-00099
Organisme : RF State Program for IBCP RAS
ID : Project №122041400114-2
Références
Nat Rev Mol Cell Biol. 2016 Apr 22;17(5):322-8
pubmed: 27103327
J Comput Chem. 2010 Mar;31(4):671-90
pubmed: 19575467
J Med Chem. 2022 Oct 13;65(19):13473-13481
pubmed: 36102846
J Biol Chem. 1989 May 15;264(14):7944-9
pubmed: 2524476
Bioorg Chem. 2019 Mar;83:380-390
pubmed: 30408650
J Chem Theory Comput. 2013 Jul 9;9(7):3084-95
pubmed: 26583988
J Biol Chem. 1990 Mar 25;265(9):4923-8
pubmed: 2138622
Eur J Med Chem. 2013 Sep;67:196-207
pubmed: 23867604
J Med Chem. 2010 Nov 25;53(22):8116-28
pubmed: 20973488
Drug Discov Today. 2022 Sep;27(9):2484-2496
pubmed: 35636722
Bioorg Med Chem Lett. 2010 Apr 1;20(7):2330-4
pubmed: 20188546
Curr Med Chem. 2016;23(11):1100-30
pubmed: 27117490
Curr Pharm Des. 2019;25(11):1312-1334
pubmed: 31465282
J Comput Chem. 2004 Oct;25(13):1605-12
pubmed: 15264254
Cancer Res. 2007 Jun 15;67(12):5865-71
pubmed: 17575155
ChemMedChem. 2014 Apr;9(4):847-54
pubmed: 24678059
Bioorg Med Chem Lett. 2018 Oct 1;28(18):3057-3063
pubmed: 30093295
J Med Chem. 2021 Sep 9;64(17):13072-13095
pubmed: 34406768
J Med Chem. 2018 Feb 22;61(4):1704-1718
pubmed: 29406710
Eur J Med Chem. 2023 Apr 5;252:115284
pubmed: 36940610
Eur J Med Chem. 2019 Jan 15;162:290-320
pubmed: 30448418
ACS Chem Biol. 2019 Dec 20;14(12):2810-2821
pubmed: 31714738
J Immunol Methods. 1983 Dec 16;65(1-2):55-63
pubmed: 6606682
J Med Chem. 2013 Sep 12;56(17):6829-44
pubmed: 23895532
Nat Rev Mol Cell Biol. 2020 Jun;21(6):307-326
pubmed: 32107477
J Med Chem. 2009 Nov 12;52(21):6752-6
pubmed: 19827778
Prog Polym Sci. 2012 Jan;37(1):106-126
pubmed: 22125349
Chem Pharm Bull (Tokyo). 1986 Oct;34(10):4150-65
pubmed: 3829149
J Med Chem. 2008 Aug 14;51(15):4771-9
pubmed: 18651728
J Comput Chem. 2010 Jan 30;31(2):455-61
pubmed: 19499576
Molecules. 2020 Dec 17;25(24):
pubmed: 33348838
J Med Chem. 2023 Mar 9;66(5):3588-3620
pubmed: 36802449
Spectrochim Acta A Mol Biomol Spectrosc. 2014 Aug 14;129:326-32
pubmed: 24747856
Future Med Chem. 2017 Oct;9(15):1765-1794
pubmed: 28929799
Pharmaceuticals (Basel). 2020 Jan 03;13(1):
pubmed: 31947889
Eur J Med Chem. 2023 Apr 5;252:115281
pubmed: 36940611
J Med Chem. 2015 Dec 24;58(24):9480-97
pubmed: 26565666
Eur J Med Chem. 2019 Jun 1;171:310-331
pubmed: 30953881
J Med Chem. 2023 Jan 12;66(1):627-640
pubmed: 36516438
J Med Chem. 2016 Jun 23;59(12):5752-65
pubmed: 27213719
Cancer Invest. 2005;23(3):264-73
pubmed: 15948296
J Med Chem. 2022 Dec 22;65(24):16372-16391
pubmed: 36511661
Cell Physiol Biochem. 2018;47(2):489-504
pubmed: 29794416
J Neurooncol. 2014 Jun;118(2):335-343
pubmed: 24740196
J Med Chem. 2009 Apr 23;52(8):2341-51
pubmed: 19296653
J Med Chem. 2014 Feb 27;57(4):1390-402
pubmed: 24502232
Eur J Med Chem. 2021 Feb 5;211:113016
pubmed: 33243532
J Comput Chem. 2013 Sep 30;34(25):2135-45
pubmed: 23832629
Pharmaceuticals (Basel). 2020 Aug 19;13(9):
pubmed: 32825171
Arch Pharm (Weinheim). 2022 May;355(5):e2100425
pubmed: 35103336
ACS Med Chem Lett. 2020 Mar 27;11(6):1185-1190
pubmed: 32550999
Molecules. 2022 Nov 26;27(23):
pubmed: 36500341
Drug Discov Today. 2022 Mar;27(3):759-776
pubmed: 34890803
Med Res Rev. 2019 Jul;39(4):1398-1426
pubmed: 30746734