Evaluation of Water-Soluble Mannich Base Prodrugs of 2,3,4,5-Tetrahydroazepino[4,3-b]indol-1(6H)-one as Multitarget-Directed Agents for Alzheimer's Disease.
Acetylcholinesterase
/ metabolism
Alzheimer Disease
/ drug therapy
Butyrylcholinesterase
/ metabolism
Cell Line, Tumor
Cell Survival
/ drug effects
Cholinesterase Inhibitors
/ chemical synthesis
Dose-Response Relationship, Drug
Humans
Mannich Bases
/ chemical synthesis
Models, Molecular
Molecular Structure
Neuroprotective Agents
/ chemical synthesis
Prodrugs
/ chemical synthesis
Solubility
Structure-Activity Relationship
Water
/ chemistry
Alzheimer disease
Mannich bases
azepinoindolone derivatives
butyrylcholinesterase inhibitor
water-soluble prodrugs
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
04 02 2021
04 02 2021
Historique:
received:
30
07
2020
revised:
17
10
2020
pubmed:
7
11
2020
medline:
11
11
2021
entrez:
6
11
2020
Statut:
ppublish
Résumé
Different Mannich base derivatives have been studied with the aim of addressing the poor aqueous solubility of the recently disclosed 6-phenethyl-2,3,4,5-tetrahydroazepino[4,3-b]indol-1(6H)-one (1), a human butyrylcholinesterase inhibitor (hBChE, IC
Identifiants
pubmed: 33156950
doi: 10.1002/cmdc.202000583
doi:
Substances chimiques
Cholinesterase Inhibitors
0
Mannich Bases
0
Neuroprotective Agents
0
Prodrugs
0
Water
059QF0KO0R
Acetylcholinesterase
EC 3.1.1.7
Butyrylcholinesterase
EC 3.1.1.8
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
589-598Subventions
Organisme : University of Bari
Organisme : Ministry of Education and Science of the Russian Federation
ID : FSSF-2020-0017
Organisme : Ministry of Education and Science of the Russian Federation
ID : 075-03-2020-223
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
“World Alzheimer Report 2018: The state of the art of dementia research: New frontiers”, C. Patterson, https://www.alz.co.uk/research/world-report-2018, 2018.
A. Kumar, A. Singh, Ekavali, Pharmacol. Rep. 2015, 67, 195-203.
F. Chiti, C. M. Dobson, Annu. Rev. Biochem. 2017, 86, 27-68.
W. J. Geldenhuys, A. S. Darvesh, Expert Rev. Neurother. 2015, 15, 3-5.
G. F. Makhaeva, S. V. Lushchekina, N. P. Boltneva, V. B. Sokolov, V. V. Grigoriev, O. G. Serebryakova, E. A. Vikhareva, A. Y. Aksinenko, G. E. Barreto, G. Aliev, et al., Sci. Rep. 2015, 5, 1-11.
Q. Li, H. Yang, Y. Chen, H. Sun, Eur. J. Med. Chem. 2017, 132, 294-309.
S. Darvesh, M. K. Cash, G. A. Reid, E. Martin, A. Mitnitski, C. Geula, J. Neuropathol. Exp. Neurol. 2012, 71, 2-14.
N. H. Greig, T. Utsuki, D. K. Ingram, Y. Wang, G. Pepeu, C. Scali, Q. S. Yu, J. Mamczarz, H. W. Holloway, T. Giordano, et al., Proc. Natl. Acad. Sci. USA 2005, 102, 17213-17218.
R. Purgatorio, M. de Candia, A. De Palma, F. De Santis, L. Pisani, F. Campagna, S. Cellamare, C. Altomare, M. Catto, Molecules 2018, 23, 1544.
J. Takahashi, I. Hijikuro, T. Kihara, M. G. Murugesh, S. Fuse, R. Kunimoto, Y. Tsumura, A. Akaike, T. Niidome, Y. Okuno, et al., Bioorg. Med. Chem. Lett. 2010, 20, 1718-1720.
J. Takahashi, I. Hijikuro, T. Kihara, M. G. Murugesh, S. Fuse, Y. Tsumura, A. Akaike, T. Niidome, T. Takahashi, H. Sugimoto, Bioorg. Med. Chem. Lett. 2010, 20, 1721-1723.
M. Shinada, F. Narumi, Y. Osada, K. Matsumoto, T. Yoshida, K. Higuchi, T. Kawasaki, H. Tanaka, M. Satoh, Bioorg. Med. Chem. 2012, 20, 4901-4914.
Y. Furukawa-Hibi, T. Alkam, A. Nitta, A. Matsuyama, H. Mizoguchi, K. Suzuki, S. Moussaoui, Q. S. Yu, N. H. Greig, T. Nagai, et al., Behav. Brain Res. 2011, 225, 222-229.
S. Darvesh, G. A. Reid, Chem.-Biol. Interact. 2016, 259, 307-312.
Y. Dgachi, L. Ismaili, D. Knez, M. Benchekroun, H. Martin, N. Szałaj, S. Wehle, O. M. Bautista-Aguilera, V. Luzet, A. Bonnet, et al., ChemMedChem 2016, 1318-1327.
M. de Candia, G. Zaetta, N. Denora, D. Tricarico, M. Majellaro, S. Cellamare, C. D. Altomare, Eur. J. Med. Chem. 2017, 125, 288-298.
R. Purgatorio, M. de Candia, M. Catto, A. Carrieri, L. Pisani, A. De Palma, M. Toma, O. A. Ivanova, L. G. Voskressensky, C. D. Altomare, Eur. J. Med. Chem. 2019, 177, 414-424.
B. M. A. Sanches, E. I. Ferreira, Int. J. Pharm. 2019, 568, 118498.
G. Roman, Eur. J. Med. Chem. 2015, 89, 743-816.
H. Bundgaard, J. Møss, J. Pharm. Sci. 1989, 78, 122-126.
A. K. Ghose, T. Herbertz, R. L. Hudkins, B. D. Dorsey, J. P. Mallamo, ACS Chem. Neurosci. 2012, 3, 50-68.
T. Cassano, A. Lopalco, M. de Candia, V. Laquintana, A. Lopedota, A. Cutrignelli, M. Perrone, R. M. Iacobazzi, G. Bedse, M. Franco, et al., Mol. Pharm. 2017, 14, 3178-3187.
H. Bundgaard, M. Johansen, J. Pharm. Sci. 1980, 69, 44-46.
I. Muszalska, A. Jankowska, Anal. Lett. 2010, 43, 1003-1018.
A. H. Kahns, H. Bundgaard, Pharm. Res. 1991, 8, 1533-1538.
B. D. Belviso, R. Caliandro, M. de Candia, G. Zaetta, G. Lopopolo, F. Incampo, M. Colucci, C. D. Altomare, J. Med. Chem. 2014, 57, 8563-8575.
D. Knez, N. Coquelle, A. Pišlar, S. Žakelj, M. Jukič, M. Sova, J. Mravljak, F. Nachon, X. Brazzolotto, J. Kos, et al., Eur. J. Med. Chem. 2018, 156, 598-617.
F. Cheng, W. Li, Y. Zhou, J. Shen, Z. Wu, G. Liu, P. W. Lee, Y. Tang, J. Chem. Inf. Model. 2012, 52, 3099-3105.
L. Pisani, R. M. Iacobazzi, M. Catto, M. Rullo, R. Farina, N. Denora, S. Cellamare, C. D. Altomare, Eur. J. Med. Chem. 2019, 161, 292-309.
H. Liu, X. Qiang, Q. Song, W. Li, Y. He, C. Ye, Z. Tan, Y. Deng, Bioorg. Med. Chem. 2019, 27, 991-1001.
E. Fabini, U. H. Danielson, J. Pharm. Biomed. Anal. 2017, 144, 188-194.
Å. Frostell-Karlsson, A. Remaeus, H. Roos, K. Andersson, P. Borg, M. Hämäläinen, R. Karlsson, J. Med. Chem. 2000, 43, 1986-1992.
R. L. Rich, Y. S. N. Day, T. A. Morton, D. G. Myszka, Anal. Biochem. 2001, 296, 197-207.
G. L. Ellman, K. D. Courtney, V. Andres, R. M. Featherstone, Biochem. Pharmacol. 1961, 7, 88-95.
G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, R. K. Belew, A. J. Olson, J. Comput. Chem. 1998, 19, 1639-1662.
L. El Khoury, D. Santos-Martins, S. Sasmal, J. Eberhardt, G. Bianco, F. A. Ambrosio, L. Solis-Vasquez, A. Koch, S. Forli, D. L. Mobley, J. Comput.-Aided Mol. Des. 2019, 33, 1011-1020.
S. Forli, A. J. Olson, J. Med. Chem. 2012, 55, 623-638.