Synthesis and acetylcholinesterase inhibitory activity of polyhydroxylated sulfated steroids: Structure/activity studies

Steroids

Volumn 78, Issue 11, 2013, Pages 1141-1147

  Richmond, Victoria ^a   Murray, Ana P ^b   Maier, Marta S ^a  

^a Ciudad Universitaria ^*  (Argentina)

^b UNIVERSIDAD NACIONAL DEL SUR   (Argentina)

Author keywords

Acetylcholinesterase activity; Sulfated steroids; Synthesis

Indexed keywords

2 ALPHA,3 ALPHA DIHYDROXY 5 ALPHA CHOLESTAN 6 ONE; 2 ALPHA,3 ALPHA EPOXY 5 ALPHA CHOLESTAN 6 ALPHA OL; 2 BETA,3 ALPHA DIHYDROXY 5 ALPHA CHOLESTAN 6 ONE; 2 BETA,3 ALPHA DIHYDROXY 5 ALPHA CHOLESTAN 6 ONE DISULFATE; 2 BETA,3 ALPHA DIHYDROXY 5 BETA CHOLESTAN 6 ONE; 2 BETA,3 ALPHA,6 ALPHA TRIHYDROXY 5 ALPHA CHOLESTANE; 2 BETA,3 ALPHA,6 BETA TRIHYDROXY 5 ALPHA CHOLESTANE; 2 BETA,3 BETA DIHYDROXY 5 ALPHA CHOLESTAN 6 ONE; 5 ALPHA CHOLEST 2 EN 6 ALPHA OL; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; DISODIUM 2 ALPHA,3 ALPHA DIHYDROXY 5 ALPHA CHOLESTAN 6 ONE DISULFATE; DISODIUM 2 BETA,3 ALPHA DIHYDROXYCHOLEST 5 ENE DISULFATE; DISODIUM 2 BETA,3 ALPHA,6 BETA TRIHYDROXY 5 ALPHA CHOLESTAN 2 BETA,3 ALPHA DISULFATE; DISODIUM 2 BETA,3 BETA DIHYDROXY 5 ALPHA CHOLESTAN 6 ONE DISULFATE; PHYSOSTIGMINE; STEROID; TRISODIUM 2 BETA,3 ALPHA,6 ALPHA TRIHYDROXY 5 ALPHA CHOLESTANE TRISULFATE; TRISODIUM 2 BETA,3 ALPHA,6 BETA TRIHYDROXY 5 ALPHA CHOLESTANE TRIISULFATE; UNCLASSIFIED DRUG;

ARTICLE; CHOLINESTERASE INHIBITION; DRUG SCREENING; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE ACTIVITY; SULFATED STEROIDS; SYNTHESIS;

ACETYLCHOLINESTERASE; ANIMALS; CHEMISTRY TECHNIQUES, SYNTHETIC; CHOLINESTERASE INHIBITORS; HYDROXYLATION; INHIBITORY CONCENTRATION 50; STEROIDS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFATES; TORPEDO;

EID: 84883450038     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2013.08.003     Document Type: Article

References (20)

1. M. Goedert, and M.G. Spillantini A century of Alzheimer's Disease Science 314 2006 777 781 (Pubitemid 44706636)
2. M. Parle, D. Dhingra, and S.K. Kulkarni Neuromodulators of learning and memory Asia Pac J Pharmacol 16 2004 89 99 (Pubitemid 40125298)
3. T.L. Rosenberry Acetylcholinesterase Adv Enzymol Relat Areas Mol Biol 43 1975 103 218
4. H. Dvir, I. Silman, M. Harel, T.L. Rosenberry, and J.L. Sussman Acetylcholinesterase: from 3D structure to function Chem Biol Interact 187 2010 10 22
5. D.-Y. Peng, Q. Sun, X.-L. Zhu, H.-Y. Lin, and Q. Chen Design, synthesis and bioevaluation of benzamides: novel AChE inhibitors with multi-functions on BChE, Aβ aggregations and β-secretase Bioorg Med Chem 20 2012 6739 6750
6. A. Enz, R. Amstutz, H. Boddeke, G. Gmelin, and J. Malonowski Brain selective inhibition of AChE: a novel approach to therapy for Alzheimer's disease Prog Brain Res 98 1993 431 435
7. R. Langjae, S. Bussarawit, S. Yuenyongsawad, K. Ingkaninan, and A. Plubrukarn Acetylcholinesterase-inhibiting steroidal alkaloid from the sponge Corticium sp Steroids 72 2007 682 685 (Pubitemid 47161089)
8. J. Porcel, and X. Montalban Anticholinesterasics in the treatment of cognitive impairment in multiple sclerosis J Neurol Sci 245 2006 177 181 (Pubitemid 43792407)
9. M.S. Vela Gurovic, M.J. Castro, V. Richmond, M.B. Faraoni, M.S. Maier, and A.P. Murray Triterpenoids with acetylcholinesterase inhibition from Chuquiraga erinacea D. Don. Subsp. erinacea (Asteraceae) Planta Medica 76 2010 607 610
10. G.A. Garrido Santos, A.P. Murray, C.A. Pujol, E.B. Damonte, and M.S. Maier Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane Steroids 68 2003 125 132 (Pubitemid 36279162)
11. V. Richmond, G. Garrido Santos, A.P. Murray, and M.S. Maier Synthesis and acetylcholinesterase inhibitory activity of 2β,3α-disulfoxy- 5α-cholestan-6-one Steroids 76 2011 1160 1165
12. H. Becker, M.A. Soler, and K.B. Sharpless Selective asymmetric dihydroxilation of polyenes Tetrahedron 51 1995 1345 1376
13. G.L. Ellman, K.D. Courtney, V. Andres Jr, and R.M. Featherstone A new and rapid colorimetric determination of acetylcholinesterase activity Biochem Pharmacol 7 1961 88 95
14. J.A. Ramirez, E.G. Gros, and L.R. Galagovsky Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs Tetrahedron 56 2000 6171 6180 (Pubitemid 30646747)
15. K.S. Jeong, P. Sjö, and K.B. Sharpless Asymmetric dihydroxylation of enynes Tetrahedron Lett 33 1992 3833 3836
16. T.N. Makarieva, L.K. Shubina, A.I. Kalinovsky, V.A. Stonik, and G.B. Elyakov Steroids in Porifera. II. Steroid derivatives from two sponges of the family Halichondriidae. Sokotrasterol sulfate, a marine steroid with a new pattern of side chain alkylation Steroids 42 1983 267 281 (Pubitemid 14152010)
17. L.J. Goad, and T. Akihisa Analysis of sterols 1997 Blackie
18. M. Murphy, B. Larrivée, I. Pollet, K.S. Craig, and D.E. Williams Identification of sokotrasterol sulfate as a novel proangiogenic steroid Circ Res 99 2006 257 265 (Pubitemid 44174933)
19. E. Podoly, T. Bruck, S. Diamant, N. Melamed-Book, and A. Weiss Human recombinant butyrylcholinesterase purified from the milk of transgenic goats interacts with beta-amyloid fibrils and suppresses their formation in vitro Neurodegener Dis 5 2008 232 236 (Pubitemid 351347859)
20. S. Diamant, E. Podoly, A. Friedler, H. Ligumsky, and O. Livnah Butyrylcholinesterase attenuates amyloid fibril formation in vitro Proc Natl Acad Sci 103 2006 8628 8633 (Pubitemid 43878071)