Radiosynthesis and whole-body distribution in mice of a
18F-labeling
butyrylcholinesterase inhibitor
in vivo distribution
neurochemistry
positron emission tomography
Journal
Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167
Informations de publication
Date de publication:
29 Dec 2023
29 Dec 2023
Historique:
revised:
03
12
2023
received:
04
09
2023
accepted:
05
12
2023
medline:
2
1
2024
pubmed:
2
1
2024
entrez:
29
12
2023
Statut:
aheadofprint
Résumé
Recently, the azepino[4,3-b]indole-1-one derivative 1 showed in vitro nanomolar inhibition against butyrylcholinesterase (BChE), the ChE isoform that plays a role in the progression and pathophysiology of Alzheimer's disease (AD), and protects against N-methyl- d-aspartate-induced neuronal toxicity. Three 9-R-substituted (R = F, Br, OMe) congeners were investigated. The 9-F derivative (2a) was found more potent as BChE inhibitors (half-maximal inhibitory concentration value = 21 nM) than 2b (9-Br) and 2c (9-OMe), achieving a residence time (38 s), assessed by surface plasmon resonance, threefold higher than that of 1. To progress in featuring the in vivo pharmacological characterization of 2a, herein the
Identifiants
pubmed: 38158335
doi: 10.1002/ardp.202300491
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2300491Subventions
Organisme : National Research Foundation of Korea (NRF)
ID : (MEST) (2021R1A2C2003301)
Organisme : Program of Regione Puglia "Research for Innovation REFIN"
ID : (POR PUGLIA FESR-FSE 2014/2020)
Organisme : Italian Ministry of Education, Universities and Research
ID : (PRIN, Grant 201744BN5T_004)
Informations de copyright
© 2023 The Authors. Archiv der Pharmazie published by Wiley-VCH GmbH on behalf of Deutsche Pharmazeutische Gesellschaft.
Références
https://www.alzint.org/resource/world-alzheimer-report-2022/ in the Alzheimer's Disease International Organiozation website.
W. J. Geldenhuys, A. S. Darvesh, Expert. Rev. Neurother. 2015, 15, 3.
F. Chiti, C. M. Dobson, Annu. Rev. Biochem. 2017, 86, 27.
D. Puzzo, J. Fiorito, R. Purgatorio, W. Gulisano, A. Palmeri, O. Arancio, R. Nicholls, in Genes, Environment and Alzheimer's Disease (Eds: O. Lazarov, G. Tesco), Academic Press, New York 2016, p. 1.
R. Wang, P. H. Reddy, J. Alzheimer's Dis. 2017, 57, 1041.
A. Silver, The Biology of Cholinesterases, North-Holland Pub. Co.; American Elsevier Pub. Co., Amsterdam; NewYork 1974.
Z. Y. Ha, S. Mathew, K. Y. Yeong, Curr. Protein Pept. Sci. 2020, 21, 99.
M. Roberson, Brain Res. Rev. 1997, 25, 50.
P. Davies, Lancet 1976, 308, 1403.
E. K. Perry, P. H. Gibson, G. Blessed, R. H. Perry, B. E. Tomlinson, J. Neurol. Sci. 1977, 34, 247.
N. H. Greig, T. Utsuki, D. K. Ingram, Y. Wang, G. Pepeu, C. Scali, Q. S. Yu, J. Mamczarz, H. W. Holloway, T. Giordano, D. Chen, K. Furukawa, K. Sambamurti, A. Brossi, D. K. Lahiri, Proc. Natl Acad. Sci. USA 2005, 102, 17213.
S. Darvesh, M. K. Cash, G. A. Reid, E. Martin, A. Mitnitski, C. Geula, J. Neuropathol. Exp. Neurol. 2012, 71, 2.
H. Xu, S. Garcia-Ptacek, L. Jönsson, A. Wimo, P. Nordström, M. Eriksdotter, Neurology 2021, 96, e2220.
S. Darvesh, Chem.-Biol. Interact. 2013, 203, 354.
A. Carotti, M. de Candia, M. Catto, T. N. Borisova, A. V. Varlamov, E. Méndez-Álvarez, R. Soto-Otero, L. G. Voskressensky, C. Altomare, Bioorg. Med. Chem. 2006, 14, 7205.
M. de Candia, G. Zaetta, N. Denora, D. Tricarico, M. Majellaro, S. Cellamare, C. D. Altomare, Eur. J. Med. Chem. 2017, 125, 288.
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.
R. Purgatorio, M. de Candia, M. Catto, M. Rullo, L. Pisani, N. Denora, A. Carrieri, A. A. Nevskaya, L. G. Voskressensky, C. D. Altomare, ChemMedChem 2021, 16, 589.
G. L. Ellman, K. D. Courtney, V. Andres, R. M. Feather-Stone, Biochem. Pharmacol. 1961, 7, 88.
M. G. Morgese, S. Schiavone, L. Trabace, Eur. J. Pharmacol. 2017, 817, 22.
S. Schiavone, P. Tucci, E. Mhillaj, M. Bove, L. Trabace, M. G. Morgese, Progr. Neuro-Psychopharmacol. Biol. Psychiatry 2017, 78, 114.
Y. I. Sheline, T. West, K. Yarasheski, R. Swarm, M. S. Jasielec, J. R. Fisher, W. D. Ficker, P. Yan, C. Xiong, C. Frederiksen, M. V. Grzelak, R. Chott, R. J. Bateman, J. C. Morris, M. A. Mintun, J. M. Lee, J. R. Cirrito, Sci. Transl. Med. 2014, 6, 236.
J. R. Cirrito, B. M. Disabato, J. L. Restivo, D. K. Verges, W. D. Goebel, A. Sathyan, D. Hayreh, G. D'Angelo, T. Benzinger, H. Yoon, J. Kim, J. C. Morris, M. A. Mintun, Y. I. Sheline, Proc. Natl Acad. Sci. USA 2011, 108, 14968.
L. Trabace, T. Cassano, A. Loverre, L. Steardo, V. Cuomo, CNS Drug Rev. 2002, 8, 53.
M. R. Marien, F. C. Colpaert, A. C. Rosenquist, Brain Res. Rev. 2004, 45, 38.
M. G. Morgese, M. Bove, M. Francavilla, S. Schiavone, S. Dimonte, A. L. Colia, M. Bevilacqua, L. Trabace, P. Tucci, Biomolecules 2021, 11, 686.
E. Galea, M. T. Heneka, C. D. Russo, D. L. Feinstein, Cell. Mol. Neurobiol. 2003, 23, 625.
S. Kalinin, V. Gavrilyuk, P. E. Polak, R. Vasser, J. Zhao, M. T. Heneka, D. L. Feinstein, Neurobiol. Aging 2007, 28, 1206.
S. Lim, D. Song, S. Jeon, Y. Kim, H. Kim, S. Lee, H. Cho, B. C. Lee, S. E. Kim, K. Kim, E. Lee, Org. Lett. 2018, 20, 7249.
F. M. Zhou, Y. Liang, J. A. Dani, Nat. Neurosci. 2001, 4, 1224.
S. Darvesh, D. L. Grantham, D. A. Hopkins, J. Comp. Neurol. 1998, 393, 374.
C. Gentzsch, X. Chen, P. Spatz, U. Košak, D. Knez, N. Nose, S. Gobec, T. Higuchi, M. Decker, Mol. Imaging Biol. 2021, 23, 505.
L. Rejc, V. Gómez-Vallejo, A. Joya, O. Moreno, A. Egimendia, P. Castellnou, X. Ríos-Anglada, U. Cossío, Z. Baz, R. Passannante, I. Tobalina-Larrea, P. Ramos-Cabrer, A. Giralt, M. Sastre, E. Capetillo-Zarate, U. Košak, D. Knez, S. Gobec, M. Marder, A. Martin, J. Llop, Theranostics 2021, 11, 6542.
S. H. Lee, N. Denora, V. Laquintana, G. F. Mangiatordi, A. Lopedota, A. Lopalco, A. Cutrignelli, M. Franco, P. Delre, I. H. Song, H. W. Kim, S. B. Kim, H. S. Park, K. Kim, S. Y. Lee, H. Youn, B. C. Lee, S. E. Kim, Eur. J. Nucl. Med. Mol. Imaging 2021, 49, 110.
M. B. Haskali, P. D. Roselt, T. J. O'Brien, C. A. Hutton, I. Ali, L. Vivash, B. Jupp, Molecules 2022, 27, 5931.
F. Cheng, W. Li, Y. Zhou, J. Shen, Z. Wu, G. Liu, P. W. Lee, Y. Tang, J. Chem. Inf. Model. 2012, 52, 3099.
R. Waterhouse, Mol. Imaging Biol. 2003, 5, 376.
D. Brockschnieder, H. Schmitt-Willich, T. Heinrich, A. Varrone, B. Gulyás, M. Toth, J. Andersson, U. Boemer, S. Krause, M. Friebe, L. Dinkelborg, C. Halldin, T. Dyrks, J. Nucl. Med. 2012, 53, 1794.
C. Gentzsch, M. Hoffmann, Y. Ohshima, N. Nose, X. Chen, T. Higuchi, M. Decker, ChemMedChem 2021, 16, 1427.
S. J. Oh, M. H. Kim, S. J. Han, K. J. Kang, I. O. Ko, Y. Kim, J.-A. Park, J. Y. Choi, K. C. Lee, D. Y. Chi, Y. J. Lee, K. M. Kim, Mol. Pharm. 2017, 14, 3114.
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.
R. Purgatorio, N. Gambacorta, M. de Candia, M. Catto, M. Rullo, L. Pisani, O. Nicolotti, C. D. Altomare, Molecules 2021, 26, 5208.
R. Purgatorio, N. Gambacorta, F. Samarelli, G. Lopopolo, M. de Candia, M. Catto, O. Nicolotti, C. D. Altomare, Molecules 2022, 27, 4269.
M. Morgese, P. Tucci, M. Colaianna, M. Zotti, V. Cuomo, S. Schiavone, L. Trabace, Curr. Pharm. Des. 2014, 20, 2539.
E. Mhillaj, M. G. Morgese, P. Tucci, A. Furiano, L. Luongo, M. Bove, S. Maione, V. Cuomo, S. Schiavone, L. Trabace, Neuroscience 2018, 372, 58.