Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step
作者： Anna Ramunno , Sandro Cosconati , Stefania Sartini , Vita Maglio , Sara Angiuoli
DOI: 10.1016/J.EJMECH.2012.02.045
关键词: Receptor 、 Inflammation 、 Pharmacology 、 Aldose reductase 、 Metastasis 、 Docking (molecular) 、 Chemistry 、 Endocrinology 、 Internal medicine 、 Diabetes mellitus 、 Fidarestat 、 Diabetic neuropathy
摘要: Aldose reductase (ALR2) is a crucial enzyme in the development of major complications diabetes mellitus. Very recently it has been demonstrated that ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-α, LPS) cause cancer (colon, breast, prostate and lung), metastasis, asthma, other diseases. Currently, fidarestat phase III clinical trial for diabetic neuropathy was found to be safe. Thus finding novel, potent inhibitors today more than past great demand as they can pave way novel therapeutic approach number diseases besides diabetes. Herein, starting from virtual screening-derived ALR2 inhibitor S12728 (1), rational receptor-based lead optimization undertaken. The design synthetic efforts here reported led discovery several new compounds endowed with low micromolar/submicromolar activities.
core.ac.uk
unisa.it
elsevier.com参考文章(38)
T P Degenhardt, J W Baynes, S R Thorpe, CHEMICAL MODIFICATION OF PROTEINS BY METHYLGLYOXAL Cellular and Molecular Biology. ,vol. 44, pp. 1139- 1145 ,(1998)
Tadashi Kataoka, Tetsuo Iwama, Tomofumi Setta, Atsuko Takagi, Preparation of Sulfonamides from Sodium Sulfonates: Ph3P ⋅ Br2 and Ph3P ⋅ Cl2 as a Mild Halogenating Reagent for Sulfonyl Bromides and Sulfonyl Chlorides Synthesis. ,vol. 1998, pp. 423- 426 ,(1998) , 10.1055/S-1998-4488
Joseph M. JEZ, Melanie J. BENNETT, Brian P. SCHLEGEL, Mitchell LEWIS, Trevor M. PENNING, Comparative anatomy of the aldo-keto reductase superfamily. Biochemical Journal. ,vol. 326, pp. 625- 636 ,(1997) , 10.1042/BJ3260625
Charles E. Grimshaw, Chung-Jeng Lai, Oxidized Aldose Reductase:In VivoFactor, Notin VitroArtifact Archives of Biochemistry and Biophysics. ,vol. 327, pp. 89- 97 ,(1996) , 10.1006/ABBI.1996.0096
Ossama El-Kabbani, Vincenzo Carbone, Connie Darmanin, Mitsuru Oka, Andre Mitschler, Alberto Podjarny, Clemens Schulze-Briese, Roland P.-T. Chung, Structure of aldehyde reductase holoenzyme in complex with the potent aldose reductase inhibitor fidarestat: implications for inhibitor binding and selectivity. Journal of Medicinal Chemistry. ,vol. 48, pp. 5536- 5542 ,(2005) , 10.1021/JM050412O
Barth�l�my Nyasse, Leif Grehn, Ulf Ragnarsson, Hernani L. S. Maia, Luis S. Monteiro, Ivo Leito, Ilmar Koppel, Juta Koppel, Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pK a of sulfonamides Journal of the Chemical Society, Perkin Transactions 1. pp. 2025- 2031 ,(1995) , 10.1039/P19950002025
Manas K. Ghorai, Amit Kumar, Deo Prakash Tiwari, BF3·OEt2-Mediated Highly Regioselective SN2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides Journal of Organic Chemistry. ,vol. 75, pp. 137- 151 ,(2010) , 10.1021/JO902244Y
Sandro Cosconati, Luciana Marinelli, Roberta Trotta, Ada Virno, Luciano Mayol, Ettore Novellino, Arthur J. Olson, Antonio Randazzo, Tandem application of virtual screening and NMR experiments in the discovery of brand new DNA quadruplex groove binders. Journal of the American Chemical Society. ,vol. 131, pp. 16336- 16337 ,(2009) , 10.1021/JA9063662
JOSHUA A. SCOTT, GEORGE L. KING, Oxidative Stress and Antioxidant Treatment in Diabetes Annals of the New York Academy of Sciences. ,vol. 1031, pp. 204- 213 ,(2004) , 10.1196/ANNALS.1331.020
Feng Shi, Man Kin Tse, Shaolin Zhou, Marga-Martina Pohl, Jörg Radnik, Sandra Hübner, Klaus Jähnisch, Angelika Brückner, Matthias Beller, Green and Efficient Synthesis of Sulfonamides Catalyzed by Nano-Ru/Fe3O4 Journal of the American Chemical Society. ,vol. 131, pp. 1775- 1779 ,(2009) , 10.1021/JA807681V