Mapping the Melatonin Receptor. 8. Selective MT2 Agonists Derived from 5,6-Dihydroindolo[2,1-a]isoquinolines and Related Systems.
5,6-dihydroindolo[2,1-a]isoquinolines
indolo[1,2-a]benzoxazines
selective MT2 agonist
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
20 06 2022
20 06 2022
Historique:
revised:
15
04
2022
received:
11
03
2022
pubmed:
29
4
2022
medline:
23
6
2022
entrez:
28
4
2022
Statut:
ppublish
Résumé
A series of substituted indolo[2,1-a]isoquinolines and indolo[1,2-a]benzoxazines have been prepared, as melatonin analogues, to investigate the nature of the binding site of the melatonin receptor. Agonist and antagonist potency of all the analogues was measured using the [35S]GTPγS binding assay protocol. The binding affinity of the analogues were measured by competition binding studies against the human MT1 (hMT1) and MT2 (hMT2) receptors stably transfected in Chinese Hamster Ovarian (CHO) cells, using 2-[
Identifiants
pubmed: 35478275
doi: 10.1002/cmdc.202200129
doi:
Substances chimiques
Benzoxazines
0
Isoquinolines
0
Ligands
0
Receptor, Melatonin, MT1
0
Receptors, Melatonin
0
Melatonin
JL5DK93RCL
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200129Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
M. L. Dubocovich, P. Delagrange, D. N. Krause, D. Sugden, D. P. Cardinali, J. Olcese, Pharmacol. Rev. 2010, 62, 343-380.
J. Arendt, Chronobiol. Int. 2006, 23, 21-37.
S. W. Holmes, D. Sugden, Br. J. Pharmacol. 1982, 76, 95-101.
A. B. Dollins, I. V. Zhdanova, R. J. Wurtman, H. J. Lynch, M. H. Deng, Proc. Natl. Acad. Sci. USA 1994, 91, 1824-1828.
K. Reid, C. Van Den Heuvel, D. Dawson, J. Sleep Res. 1996, 5, 150-154.
D. Garfinkel, M. Laudon, D. Nof, N. Zisapel, Lancet 1995, 346, 541-544.
R. M. Hagan, N. R. Oakley, Trends Pharmacol. Sci. 1995, 16, 81-83.
P. Delagrange, B. Guardiola-Lemaitre, Clin. Neuropharmacol. 1997, 20, 482-510.
W. Ruan, X. Yuan, H. K. Eltzschig, Nat. Rev. Drug Discovery 2021, 20, 287-307.
J. A. Boutin, R. Jockers, J. Pineal Res. 2021, 70, 1-14.
R. J. Reiter, J. C. Mayo, D. X. Tan, R. M. Sainz, M. Alatorre-Jimenez, L. Qin, J. Pineal Res. 2016, 61, 253-278.
A. Tarocco, N. Caroccia, G. Morciano, M. R. Wieckowski, G. Ancora, G. Garani, P. Pinton, Cell Death Dis. 2019, 10, 1-12.
A. K. Jaworek, J. C. Szepietowski, P. Hałubiec, A. Wojas-Pelc, J. Jaworek, Antioxidants 2021, 10, 1179.
M. Vlachou, A. Siamidi, A. Dedeloudi, S. K. Konstantinidou, I. P. Papanastasiou, Int. J. Mol. Med. 2021, 47, 1-9.
K. M. Cross, D. M. Landis, L. Sehgal, J. D. Payne, Endocr. Pract. 2021, 27, 850-855.
S. M. Reppert, D. R. Weaver, C. Godson, Trends Pharmacol. Sci. 1996, 17, 100-102.
S. M. Reppert, D. R. Weaver, T. Ebisawa, Neuron 1994, 13, 1177-1185.
S. M. Reppert, C. Godson, C. D. Mahle, D. R. Weaver, S. A. Slaugenhaupt, J. F. Gusella, Proc. Natl. Acad. Sci. USA 1995, 92, 8734-8738.
S. M. Reppert, J. Biol. Rhythms 1997, 12, 528-531.
S. M. Reppert, D. R. Weaver, V. M. Cassone, C. Godson, L. F. Kolakowski, Neuron 1995, 15, 1003-1015.
C. Gautier, S.-P. Guenin, I. Riest-Fery, T. J. Perry, C. Legros, O. Nosjean, V. Simonneaux, F. Grützner, J. A. Boutin, PLoS One 2018, 13, e0191904.
E. L. Bittman, D. R. Weaver, Biol. Reprod. 1990, 43, 986-993.
B. Stauch, L. C. Johansson, J. D. McCorvy, N. Patel, G. W. Han, X. P. Huang, C. Gati, A. Batyuk, S. T. Slocum, A. Ishchenko, W. Brehm, T. A. White, N. Michaelian, C. Madsen, L. Zhu, T. D. Grant, J. M. Grandner, A. Shiriaeva, R. H. J. Olsen, A. R. Tribo, S. Yous, R. C. Stevens, U. Weierstall, V. Katritch, B. L. Roth, W. Liu, V. Cherezov, Nature 2019, 569, 284-288.
L. C. Johansson, B. Stauch, J. D. McCorvy, G. W. Han, N. Patel, X. P. Huang, A. Batyuk, C. Gati, S. T. Slocum, C. Li, J. M. Grandner, S. Hao, R. H. J. Olsen, A. R. Tribo, S. Zaare, L. Zhu, N. A. Zatsepin, U. Weierstall, S. Yous, R. C. Stevens, W. Liu, B. L. Roth, V. Katritch, V. Cherezov, Nature 2019, 569, 289-292.
M. Izuhara, K. Kawano, K. Otsuki, S. Hashioka, M. Inagaki, Sleep Med. 2021, 80, 100-104.
M. Sanches, J. Quevedo, J. C. Soares, Prog. Neuro-Psychopharmacology Biol. Psychiatry 2021, 106, 110157.
P. Garratt, A. Tsotinis, Mini-Rev. Med. Chem. 2007, 7, 1075-1088.
D. P. Zlotos, R. Jockers, E. Cecon, S. Rivara, P. A. Witt-Enderby, J. Med. Chem. 2014, 57, 3161-3185.
E. Wauters, K. Thevissen, C. Wouters, F. M. Bosisio, F. De Smet, J. Gunst, S. Humblet-Baron, D. Lambrechts, A. Liston, P. Matthys, J. Neyts, P. Proost, B. Weynand, J. Wauters, S. Tejpar, A. D. Garg, Front. Immunol. 2020, 11, DOI 10.3389/fimmu.2020.01642.
A. Tsotinis, I. P. Papanastasiou, in Melatonin - Horm. Darkn. Its Ther. Potential Perspect., IntechOpen, 2020.
J. A. Boutin, P. A. Witt-Enderby, C. Sotriffer, D. P. Zlotos, J. Pineal Res. 2020, 69, 1-18.
P. J. Garratt, R. Jones, S. J. Rowe, D. Sugden, Bioorg. Med. Chem. Lett. 1994, 4, 1555-1558.
P. J. Garratt, S. Travard, S. Vonhoff, A. Tsotinis, D. Sugden, J. Med. Chem. 1996, 39, 1797-1805.
A. Carocci, A. Catalano, A. Lovece, G. Lentini, A. Duranti, V. Lucini, M. Pannacci, F. Scaglione, C. Franchini, Bioorg. Med. Chem. 2010, 18, 6496-6511.
Y. Hu, M. K. C. Ho, K. H. Chan, D. C. New, Y. H. Wong, Bioorg. Med. Chem. Lett. 2010, 20, 2582-2585.
J. Zhu, Y. Hu, M. K. C. Ho, Y. H. Wong, Xenobiotica 2011, 41, 35-45.
P. J. Garratt, S. Vonhoff, S. J. Rowe, D. Sugden, Bioorg. Med. Chem. Lett. 1994, 4, 1559-1564.
A. Tsotinis, P. A. Afroudakis, P. J. Garratt, A. Bocianowska-Zbrog, D. Sugden, ChemMedChem 2014, 9, 2238-2243.
D. J. Davies, P. J. Garratt, D. A. Tocher, S. Vonhoff, J. Davies, M. T. Teh, D. Sugden, J. Med. Chem. 1998, 41, 451-467.
S. Copinga, P. G. Tepper, C. J. Grol, A. S. Horn, M. L. Dubocovich, J. Med. Chem. 1993, 36, 2891-2898.
V. Leclerc, P. Depreux, D. Lesieur, D. H. Caignard, P. Renard, P. Delagrange, B. Guardiola-Lemaitre, P. Morgan, Bioorg. Med. Chem. Lett. 1996, 6, 1071-1076.
J. M. Jansen, S. Copinga, G. Gruppen, E. J. Molinari, M. L. Dubocovich, C. J. Grol, Bioorg. Med. Chem. 1996, 4, 1321-1332.
C. J. Grol, J. M. Jansen, Bioorg. Med. Chem. 1996, 4, 1333-1339.
M. Mathé-Allainmat, F. Gaudy, S. Sicsic, A. L. Dangy-Caye, S. Shen, B. Brémont, Z. Benatalah, M. Langlois, P. Renard, P. Delagrange, J. Med. Chem. 1996, 39, 3089-3095.
A. Tsotinis, R. Kompogennitaki, I. Papanastasiou, P. J. Garratt, A. Bocianowska, D. Sugden, MedChemComm 2019, 460-464.
K. H. Chan, Y. H. Wong, Int. J. Mol. Sci. 2013, 14, 18385-18406.
N. Wan, F.-F. Zhang, J. Ju, D.-Z. Liu, S.-Y. Zhou, B.-L. Zhang, Mini-Rev. Med. Chem. 2013, 13, 1462-1474.
R. Faust, P. J. Garratt, R. Jones, L. K. Yeh, A. Tsotinis, M. Panoussopoulou, T. Calogeropoulou, M. T. Teh, D. Sugden, J. Med. Chem. 2000, 43, 1050-1061.
A. P. Kozikowski, D. Ma, Tetrahedron Lett. 1991, 32, 3317-3320.
R. B. Petigara, H. L. Yale, J. Heterocycl. Chem. 1974, 11, 331-337.
V. Audinot, F. Mailliet, C. Lahaye-Brasseur, A. Bonnaud, A. Le Gall, C. Amossé, S. Dromaint, M. Rodriguez, N. Nagel, J. P. Galizzi, B. Malpaux, G. Guillaumet, D. Lesieur, F. Lefoulon, P. Renard, P. Delagrange, J. A. Boutin, Naunyn-Schmiedeberg′s Arch. Pharmacol. 2003, 367, 553-561.
J. A. Boutin, F. Bouillaud, E. Janda, I. Gacsalyi, G. Guillaumet, E. C. Hirsch, D. A. Kane, F. Nepveu, K. Reybier, P. Dupuis, M. Bertrand, M. Chhour, T. Le Diguarher, M. Antoine, K. Brebner, H. Da Costa, P. Ducrot, A. Giganti, V. Goswami, H. Guedouari, P. P. Michel, A. Patel, J. Paysant, J. Stojko, M.-C. Viaud-Massuard, G. Ferry, S. Francis, Mol. Pharmacol. Mol Pharmacol 2019, 95, 269-285.