Calixarenes Incorporating Sulfonamide Moieties: Versatile Ligands for Carbonic Anhydrases Inhibition.
benzensulfonamide
calixarenes
carbonic anhydrases
carbonic anhydrases X-ray crystal structure
enzyme inhibition
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
27 Jan 2022
27 Jan 2022
Historique:
received:
28
09
2021
pubmed:
10
12
2021
medline:
1
2
2022
entrez:
9
12
2021
Statut:
ppublish
Résumé
Carbonic anhydrases (CAs) continue to represent a relevant pharmaceutical target. The need of selective inhibitors and the involvement of these metalloenzymes in many multifaceted diseases boost the search for new ligands able to distinguish among the different CA isoforms, and for multifunctional systems simultaneously able to inhibit CAs and to interfere with other pathological events by interacting with additional targets. In this work, we successfully explored the possibility of preparing new CAs ligands by combining calixarenes with benzensulfonamide units. Inhibition tests towards three human CA isoforms evidenced, for some of the ligands, K
Identifiants
pubmed: 34882858
doi: 10.1002/chem.202103527
doi:
Substances chimiques
Carbonic Anhydrase Inhibitors
0
Ligands
0
Sulfonamides
0
Calixarenes
130036-26-9
Carbonic Anhydrases
EC 4.2.1.1
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202103527Subventions
Organisme : Ministero dell'Università e della Ricerca
ID : PRIN 2017E44A9P
Organisme : Ministero dell'Università e della Ricerca
ID : PRIN prot. 2017XYBP2R
Organisme : Ministero dell'Università e della Ricerca
ID : FISR2019_04819 BacCAD
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
T. H. Maren, Physiol. Rev. 1967, 47, 595-781.
C. T. Supuran, Biochem. J. 2016, 473, 2023-2032.
C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2012, 27, 759-772.
C. T. Supuran, Nature Rev. Drug Dis. 2008, 7, 168-181;
C. T. Supuran, Clin. Sci. 2021, 135, 1233-1249.
E. Berrino, L. Milazzo, L. Micheli, D. Vullo, A. Angeli, M. Bozdag, A. Nocentini, M. Menicatti, G. Bartolucci, L. di Cesare Mannelli, C. Ghelardini, C. T. Supuran, F. Carta, J. Med. Chem. 2019, 62, 7233-7249.
M. Gallorini, A. C. Berardi, A. Ricci, C. Antonetti Lamorgese Passeri, S. Zara, F. Oliva, A. Cataldi, F. Carta, S. Carradori, Biomedicine 2021, 9, 141-157.
N. Krall, F. Pretto, D. Neri, Chem. Sci. 2014, 5, 3640-3644;
N. Krall, F. Pretto, W. Decurtins, G. J. L. Bernardes, C. T. Supuran, D. Neri, Angew. Chem. Int. Ed. 2014, 53, 4231-4235;
Angew. Chem. 2014, 126, 4315-4320.
H. S. Jung, J. Han, H. Shi, S. Koo, H. Singh, H.-J. Kim, J. L. Sessler, J. Y. Lee, J.-H. Kim, J. S. Kim, J. Am. Chem. Soc. 2017, 139, 7595-7602.
A. Angeli, L. Di Cesare Mannelli, C. Ghelardini, T. S. Peat, G. Bartolucci, M. Menicatti, F. Carta, C. T. Supuran, Eur. J. Med. Chem. 2019, 177, 188-197.
J. A. Aaron, J. M. Chambers, K. M. Jude, L. Di Costanzo, I. J. Dmochowski, D. W. Christianson, J. Am. Chem. Soc. 2008, 130, 6942-6943;
J. M. Chambers, P. Aru Hill, J. A. Aaron, Z. Han, D. W. Christianson, N. N. Kuzma, I. J. Dmochowski, J. Am. Chem. Soc. 2009, 131, 563-569.
V. Alterio, A. Di Fiore, K. D'Ambrosio, C. T. Supuran, G. De Simone, Chem. Rev. 2012, 112, 4421-4468.
M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. Int. Ed. 1998, 37, 2754-2794Angew. Chem. 1998, 110, 2908-2953;
Angew. Chem. 1998, 110, 2908-2953;
Angew. Chem. Int. Ed. 1998, 37, 2754-2794;
C. Fasting, C. A. Schalley, M. Weber, O. Seitz, S. Hecht, B. Koksch, J. Dernedde, C. Graf, E.-W. Knapp, R. Haag, Angew. Chem. Int. Ed. Engl. 2012, 51, 10472-10498;
Angew. Chem. 2012, 124, 10622-10650;
Angew. Chem. Int. Ed. 2012, 51, 10472-10498;
J. Huskens, L. J. Prins, R. Haag, B. J. Ravoo, in Multivalency: Concepts, Research & Applications, Wiley, 2018.
N. Kanfar, E. Bartolami, R. Zelli, A. Marra, J.-Y. Winum, S. Ulrich, P. Dumy, Org. Biomol. Chem. 2015, 13, 9894-9906;
S. G. Gouin, Chem. Eur. J. 2014, 20, 11616-11628;
P. Compain, Chem. Rec. 2020, 20, 10-22;
A. Joosten, C. Decroocq, J. de Sousa, J. P. Schneider, E. Etamé, A. Bodlenner, T. D. Butters, P. Compain, ChemBioChem 2014, 15, 309-319;
E. Howard, A. Cousido-Siah, M. L. Lepage, J. P. Schneider, A. Bodlenner, A. Mitschler, A. Meli, I. Izzo, H. A. Alvarez, A. Podjarny, P. Compain, Angew. Chem. Int. Ed. 2018, 57, 8002-8006;
Angew. Chem. 2018, 130, 8134-8138.
F. Carta, P. Dumy, C. T. Supuran, J.-Y. Winum, Int. J. Mol. Sci. 2019, 20, 5352-5365.
M. Stiti, A. Cecchi, M. Rami, M. Abdaoui, V. Barragan-Montero, A. Scozzafava, Y. Guari, J.-Y. Winum, C. T. Supuran, J. Am. Chem. Soc. 2008, 130, 16130-16131.
M. Abellán-Flos, M. Tanç, C. T. Supuran, S. P. Vincent, Org. Biomol. Chem. 2015, 13, 7445-7451.
S. M. Sebti, A. D. Hamilton, Oncogene 2000, 19, 6566-6573;
V. Martos, S. C. Bell, E. Santos, E. Y. Isacoff, D. Trauner, J. de Mendoza, Proc. Natl. Acad. Sci. USA 2009, 106, 10482-10486.
S. Cecioni, R. Lalor, B. Blanchard, J. P. Praly, A. Imberty, S. E. Matthews, S. Vidal, Chem. Eur. J. 2009, 15, 13232-13240;
S. André, F. Sansone, H. Kaltner, A. Casnati, J. Kopitz, H. J. Gabius, R. Ungaro, ChemBioChem 2008, 9, 1649-1661;
J. Garcia-Hartjes, S. Bernardi, C. A. G. M. Weijers, T. Wennekes, M. Gilbert, F. Sansone, A. Casnati, H. Zuilhof, Org. Biomol. Chem. 2013, 11, 4340-4349.
V. Bagnacani, F. Sansone, G. Donofrio, L. Baldini, A. Casnati, R. Ungaro, Org. Lett. 2008, 10, 3953-3956;
V. Bagnacani, V. Franceschi, M. Bassi, M. Lomazzi, G. Donofrio, F. Sansone, A. Casnati, R. Ungaro, Nat. Commun. 2013, 4 : 1721.
M. Gómez-García, J. M. Benito, A. P. Butera, C. Ortiz Mellet, J. M. García Fernández, J. L. Jiménez Blanco, J. Org. Chem. 2012, 77, 1273-1288;
M. González-Cuesta, D. Goyard, E. Nanba, K. Higaki, J. M. García Fernández, O. Renaudet, C. Ortiz Mellet, Chem. Commun. 2019, 55, 12845-12848;
X. Ferhati, C. Matassini, M. G. Fabbrini, A. Goti, A. Morrone, F. Cardona, A. J. Moreno-Vargas, P. Paoli, Bioorg. Chem. 2019, 87, 534-549.
M. Oguza, E. Kalay, S. Akocak, A. Nocentini, N. Lolak, M. Boga, M. Yilmaz, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2020, 35, 1215-1223.
A. Scozzafava, L. Menabuoni, F. Mincione, F. Briganti, G. Mincione, C. T. Supuran, J. Med. Chem. 1999, 42, 2641-2650;
K. D′Ambrosio, F.-Z. Smaine, F. Carta, G. De Simone, J.-Y. Winum, C. T. Supuran, J. Med. Chem. 2012, 55, 6776-6783;
C. T. Supuran, Expert Opin. Drug Discovery 2020, 15, 671-686.
R. G. Khalifah, J. Biol. Chem. 1971, 246, 2561-2573.
A. M. Zhanga, N. Weia, X. F. Liua, M. G. Wub, G. S. Xuan, Russ. J. Bioorg. Chem. 2021, 47, 261-269.
A. Angeli, D. Tanini, A. Capperucci, G. Malevolti, F. Turco, M. Ferraroni, C. T. Supuran, Bioorg. Chem. 2018, 81, 642-648.
A. R. N. S. Royappa, M. Ayer, A. Fracassi, M.-O Ebert, S. Aroua, Y. Yamakoshi, Helv. Chim. Acta 2017, 100, e1600391.
A. Ikeda, T. Tsudera, S. Shinkai, J. Org. Chem. 1997, 62, 3568-3574.
L. Baldini, M. Melegari, V. Bagnacani, A. Casnati, E. Dalcanale, F. Sansone, R. Ungaro, J. Org. Chem. 2011, 76, 3720-3732.
V. Bagnacani, V. Franceschi, L. Fantuzzi, F. Sansone, G. Donofrio, A. Casnati, R. Ungaro, Bioconjugate Chem. 2012, 23, 993-1002.
A. Casnati, N. Della Ca’, M. Fontanella, F. Sansone, F. Ugozzoli, R. Ungaro, K. Liger, J.-F. Dozol, Eur. J. Org. Chem. 2005, 2338-2348.
J. D. Van Loom, R. G. Janssen, W. Verboom, D. N. Reinhoudt, Tetrahedron Lett. 1992, 33, 5125-5128.
N. E. Behnke, R. Kielawa, D.-H. Kwon, D. H. Ess, L. Kürti, Org. Lett. 2018, 20, 8064-8068.
A. Angeli, L. Di Cesare Mannelli, E. Lucarini, T. S. Peat, C. Ghelardini, C. T. Supuran, Eur. J. Med. Chem. 2018, 154, 210-219;
O. Akgul, L. Di Cesare Mannelli, D. Vullo, A. Angeli, C. Ghelardini, G. Bartolucci, A. S. Alfawaz Altamimi, A. Scozzafava, C. T. Supuran, F. Carta, J. Med. Chem. 2018, 61, 4961-4977;
L. Vats, V. Sharma, A. Angeli, R. Kumar, C. T. Supuran, P. K. Sharma, Eur. J. Med. Chem. 2018, 150, 678-686;
E. Bruno, M. R. Buemi, A. Di Fiore, L. De Luca, S. Ferro, A. Angeli, R. Cirilli, D. Sadutto, V. Alterio, S. M. Monti, C. T. Supuran, G. De Simone, R. Gitto, J. Med. Chem. 2017, 60, 4316-4326.
W. Kabsch, Acta Crystallogr. Sect. D 2010, 66, 125-132.
G. N. Murshudov, P. Skubak, A. A. Lebedev, N. S. Pannu, R. A. Steiner, R. A. Nicholls, M. D. Winn, F. Long, A. A. Vagin, Acta Crystallogr. Sect. D 2011, 67, 355-367.
A. A. Lebedev, P. Young, M. N. Isupov, O. V. Moroz, A. A. Vagin, G. N. Murshudov, Acta Crystallogr. Sect. D 2012, 68, 431-440.
P. Emsley, B. Lohkamp, W. G. Scott, K. Cowtan, Acta Crystallogr. Sect. D 2010, 66, 486-501.
V. S. Lamzin, A. Perrakis, K. S. Wilson, in Crystallography of Biological Macromolecules (Eds.: M. G. Rossmann, E. Arnold), Kluwer Academic Publishers, Dordrecht, The Netherlands, 2001, p. 720.
S. C. Lovell, I. W. Davis, W. B. Arendall III, P. I. W. de Bakker, J. M. Word, M. G. Prisant, J. S. Richardson, D. C. Richardson, Proteins 2003, 50, 437-450.
E. F. Pettersen, T. D. Goddard, C. C. Huang, G. S. Couch, D. M. Greenblatt, E. C. Meng, T. E. Ferrin, J. Comput. Chem. 2004, 25, 1605-1612.
C. A. Behnke, I. Le Trong, J. W. Godden, E. A. Merritt, D. C. Teller, J. Bajorath, R. E. Stenkampa, Acta Crystallogr. Sect. D 2010, 66, 616-627;
RCSB Protein Data Bank: powerful new tools for exploring 3D structures of biological macromolecules for basic and applied research and education in fundamental biology, biomedicine, biotechnology, bioengineering and energy sciences. Nucleic Acids Res. 2021, 49, D437-D451.
Schrödinger Suite Release 2019-1, Schrödinger, LLC, New York, NY, 2019:
Prime, v.5.5;
Maestro v.11.9;
Epik, v.4.7;
Impact, v.8.2;
Macromodel v.12.3;
Glide, v.8.2;
Desmond, v.5.7;
Jaguar, v. 10.3.
F. H. Allen, Acta Crystallogr. Sect. B 2002, 58, 380-388. The CSD version used in this work was updated in 2021.
A. Pustenko, A. Nocentini, P. Gratteri, A. Bonardi, I. Vozny, R. Žalubovskis, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2020, 35, 1011-1020;
A. Bonardi, A. Nocentini, R. Cadoni, S. del Prete, P. Dumy, C. Capasso, P. Gratteri, C. T. Supuran, J.-Y. Winum, ACS Med. Chem. Lett. 2020, 11, 2277-2284;
A. Nocentini, A. Bonardi, P. Gratteri, B. Cerra, A. Gioiello, C. T. Supuran, J. Enzyme Inhib. Med. Chem. 2018, 33, 1453-1459.