Synthesis of Pyridoclax Analogues: Insight into Their Druggability by Investigating Their Physicochemical Properties and Interactions with Membranes.
Analytical methods
medicinal chemistry
membrane models
oligopyridines
structure-activity relationships
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
07 01 2020
07 01 2020
Historique:
received:
23
09
2019
revised:
30
10
2019
pubmed:
20
11
2019
medline:
29
1
2021
entrez:
20
11
2019
Statut:
ppublish
Résumé
Pyridoclax is considered a promising anticancer drug, acting as a protein-protein interaction disruptor, with potential applications in the treatment of ovarian, lung, and mesothelioma cancers. Eighteen sensibly selected structural analogues of Pyridoclax were synthesized, and their physicochemical properties were systematically assessed and analyzed. Moreover, considering that drug-membrane interactions play an essential role in understanding the mode of action of a given drug and its eventual toxic effects, membrane models were used to investigate such interactions in bulk (liposomes) and at the air-water interface. The measured experimental data on all original oligopyridines allowed the assessment of relative differences in terms of physicochemical properties, which could be determinant for their druggability, and hence for drug development.
Identifiants
pubmed: 31743599
doi: 10.1002/cmdc.201900542
doi:
Substances chimiques
Liposomes
0
Octanols
0
Pyridines
0
pyridoclax
0
Water
059QF0KO0R
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
136-154Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
R. Beroukhim, C. H. Mermel, D. Porter, G. Wei, S. Raychaudhuri, J. Donovan, J. Barretina, J. S. Boehm, J. Dobson, M. Urashima, Nature 2010, 463, 899-905.
A. Frenzel, F. Grespi, W. Chmelewskij, A. Villunger, Apoptosis 2009, 14, 584-596.
E. Brotin, M. Meryet-Figuière, K. Simonin, R. E. Duval, M. Villedieu, J. Leroy-Dudal, E. Saison-Behmoaras, P. Gauduchon, C. Denoyelle, L. Poulain, Int. J. Cancer 2010, 126, 885-895.
C. Gloaguen, A. S. Voisin-Chiret, J. Sopkova-de Oliveira Santos, J. Fogha, F. Gautier, M. De Giorgi, G. Burzicki, S. Perato, C. Pétigny-Lechartier, K. Simonin-Le Jeune, J. Med. Chem. 2015, 58, 1644-1668.
C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Delivery Rev. 1997, 23, 3-25.
C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Delivery Rev. 2001, 46, 3-26.
G. L. Amidon, H. Lennernäs, V. P. Shah, J. R. Crison, Pharm. Res. 1995, 12, 413-420.
A. Bouillon, A. S. Voisin, A. Robic, J.-C. Lancelot, V. Collot, S. Rault, J. Org. Chem. 2003, 68, 10178-10180.
A. S. Voisin-Chiret, A. Bouillon, G. Burzicki, M. Célant, R. Legay, H. El-Kashef, S. Rault, Tetrahedron 2009, 65, 607-612.
A. S. Voisin-Chiret, S. Rault, Pure Appl. Chem. 2012, 84, 2467-2478.
G. Burzicki, A. S. Voisin-Chiret, J. S. Oliveira Santos, S. Rault, Tetrahedron 2009, 65, 5413-5417.
G. Burzicki, A. S. Voisin-Chiret, J. S. O. Santos, S. Rault, Synthesis 2010, 2804-2810.
S. Perato, A. S. Voisin-Chiret, J. Sopková-de Oliveira Santos, R. Legay, H. Oulyadi, S. Rault, Tetrahedron 2012, 68, 1910-1917.
A. S. Voisin-Chiret, M. Muraglia, G. Burzicki, S. Perato, F. Corbo, J. Sopková-de Oliveira Santos, C. Franchini, S. Rault, Tetrahedron 2010, 66, 8000-8005.
M. De Giorgi, A. S. Voisin-Chiret, J. Sopková-de Oliveira Santos, F. Corbo, C. Franchini, S. Rault, Tetrahedron 2011, 67, 6145-6154.
S. Perato, M. De Giorgi, G. Burzicki, F. Legalite, S. Rault, A. S. Voisin-Chiret, Curr. Microw. Chem. 2014, 1, 75-80.
A. S. Voisin-Chiret, G. Burzicki, S. Perato, M. De Giorgi, C. Franchini, J. Sopková-de Oliveira Santos, S. Rault, Tetrahedron 2012, 68, 4381-4389.
S. Hedir, M. De Giorgi, J. Fogha, M. De Pascale, L.-B. Weiswald, E. Brotin, B. Marekha, C. Denoyelle, C. Denis, P. Suzanne, Eur. J. Med. Chem. 2018, 159, 357-380.
D. F. Veber, S. R. Johnson, H.-Y. Cheng, B. R. Smith, K. W. Ward, K. D. Kopple, J. Med. Chem. 2002, 45, 2615-2623.
R. Didziapetris, P. Japertas, A. Avdeef, A. Petrauskas, J. Drug Targeting 2003, 11, 391-406.
Z. Rankovic, J. Med. Chem. 2015, 58, 2584-2608.
A. Avdeef, Absorption and Drug Development: Solubility, Permeability, and Charge State, John Wiley & Sons, 2003.
Y. Ran, S. H. Yalkowsky, J. Chem. Inf. Comput. Sci. 2001, 41, 354-357.
T. J. Ritchie, S. J. F. Macdonald, R. J. Young, S. D. Pickett, Drug Discovery Today 2011, 16, 164-171.
Y. Henchoz, D. Guillarme, S. Martel, S. Rudaz, J.-L. Veuthey, P.-A. Carrupt, Anal. Bioanal. Chem. 2009, 394, 1919-1930.
J. Lalut, B. B. Tournier, T. Cailly, C. Lecoutey, S. Corvaisier, A. Davis, C. Ballandonne, M. Since, P. Millet, F. Fabis, Eur. J. Med. Chem. 2016, 116, 90-101.
V. N. Viswanadhan, A. K. Ghose, G. R. Revankar, R. K. Robins, J. Chem. Inf. Comput. Sci. 1989, 29, 163-172.
R. Mannhold, G. I. Poda, C. Ostermann, I. V. Tetko, J. Pharm. Sci. 2009, 98, 861-893.
M. Ishikawa, Y. Hashimoto, J. Med. Chem. 2011, 54, 1539-1554.
X.-Q. Chen, O. S. Gudmundsson, M. J. Hageman, J. Med. Chem. 2012, 55, 7945-7956.
A.-C. Groo, M. De Pascale, A.-S. Voisin-Chiret, S. Corvaisier, M. Since, A. Malzert-Fréon, Eur. J. Pharm. Sci. 2017, 97, 218-226.
M. Kansy, F. Senner, K. Gubernator, J. Med. Chem. 1998, 41, 1007-1010.
P. Wils, A. Warnery, V. Phung-Ba, S. Legrain, D. Scherman, J. Pharmacol. Exp. Ther. 1994, 269, 654-658.
S. S. F. Leung, D. Sindhikara, M. P. Jacobson, J. Chem. Inf. Model. 2016, 56, 924-929.
M. Lúcio, J. L. F. C. Lima, S. Reis, Curr. Med. Chem. 2010, 17, 1795-1809.
F. Castelli, A. Raudino, M. Fresta, J. Colloid Interface Sci. 2005, 285, 110-117.
M. Engelk, P. Bojarski, R. Bloss, H. Diehl, Biophys. Chem. 2001, 90, 157-173.
R. Pignatello, T. Musumeci, L. Basile, C. Carbone, G. Puglisi, J. Pharm. Bioallied Sci. 2011, 3, 4-14.
T. T. Mills, J. Huang, G. W. Feigenson, J. F. Nagle, Gen. Physiol. Biophys. 2009, 28, 126-139.
W. Smeralda, M. Since, S. Corvaisier, R. Legay, A.-S. Voisin-Chiret, A. Malzert-Freon, Eur. J. Pharm. Sci. 2019, 131, 75-83.
J. D. Knight, A. D. Miranker, J. Mol. Biol. 2004, 341, 1175-1187.
D. Iacopetta, C. Rosano, F. Puoci, O. I. Parisi, C. Saturnino, A. Caruso, P. Longo, J. Ceramella, A. Malzert-Fréon, P. Dallemagne, Eur. J. Pharm. Sci. 2017, 96, 263-272.
N. S. Hatzakis, V. K. Bhatia, J. Larsen, K. L. Madsen, P.-Y. Bolinger, A. H. Kunding, J. Castillo, U. Gether, P. Hedegård, D. Stamou, Nat. Chem. Biol. 2009, 5, 835-841.
S. S. Y. Chong, S. G. Taneva, J. M. C. Lee, R. B. Cornell, Biochemistry 2014, 53, 450-461.
R. W. Gunasekara, Y. Zhao, Langmuir 2015, 31, 3919-3925.
J. Ren, S. Lew, Z. Wang, E. London, Biochemistry 1997, 36, 10213-10220.
F. R. Maxfield, I. Tabas, Nature 2005, 438, 612-621.
K. M. Taylor, M. A. Roseman, Biochemistry 1995, 34, 3841-3850.
D. Illinger, G. Duportail, Y. Mely, N. Poirel-Morales, D. Gerard, J. G. Kuhry, Biochim. Biophys. Acta 1995, 1239, 58-66.
H. Ferreira, M. Lúcio, B. de Castro, P. Gameiro, J. L. F. C. Lima, S. Reis, Anal. Bioanal. Chem. 2003, 377, 293-298.
O. Stern, M. Volmer, 1919, 20, 183-188.
M. Pinheiro, S. Pisco, A. S. Silva, C. Nunes, S. Reis, Int. J. Pharm. 2014, 466, 190-197.
C. Nunes, D. Lopes, M. Pinheiro, C. Pereira-Leite, S. Reis, Pharm. Res. 2013, 30, 2097-2107.
L. W. Thomas, C. Lam, S. W. Edwards, FEBS Lett. 2010, 584, 2981-2989.
Discovery Studio Modeling Environment, Release 3.5, BIOVIA, San Diego, CA, 2012.
Schrödinger Release 2015-2, Schrödinger, LLC, New York, NY, 2017.
B. Bard, S. Martel, P.-A. Carrupt, Eur. J. Pharm. Sci. 2008, 33, 230-240.
F. Olson, C. A. Hunt, F. C. Szoka, W. J. Vail, D. Papahadjopoulos, Biochim. Biophys. Acta 1979, 557, 9-23.
R. A. Demel, W. S. Geurts van Kessel, R. F. Zwaal, B. Roelofsen, L. L. van Deenen, Biochim. Biophys. Acta 1975, 406, 97-107.
B. Berge, A. Renault, EPL Europhys. Lett. 1993, 21, 773.
M. Deleu, J.-M. Crowet, M. N. Nasir, L. Lins, Biochim. Biophys. Acta 2014, 1838, 3171-3190.
C. Bourlieu, G. Paboeuf, S. Chever, S. Pezennec, J.-F. Cavalier, F. Guyomarc'h, A. Deglaire, S. Bouhallab, D. Dupont, F. Carrière, Colloids Surf. B 2016, 143, 97-106.