Inhibition requirements of the human apical sodium-dependent bile acid transporter (hASBT) using aminopiperidine conjugates of glutamyl-bile acids

Pharmaceutical Research

Volumn 26, Issue 7, 2009, Pages 1665-1678

  González, Pablo M ^a,b   Acharya, Chayan ^a   MacKerell Jr , Alexander D ^a   Polli, James E ^a  

^a UNIVERSITY OF MARYLAND SCHOOL OF PHARMACY   (United States)

^b PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

Apical sodium dependent bile acid transporter; Bile acid; CHARMM; Conformationally sampled pharmacophore; Transporter

Indexed keywords

AMINOPIPERIDINE; BILE ACID; CARBON; GLUTAMIC ACID; GLUTAMYL BILE ACID DERIVATIVE; NITROGEN; PIPERIDINE; SODIUM; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; ESTERIFICATION; HYDROPHOBICITY; PHARMACOPHORE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN SYNTHESIS; PROTEIN TRANSPORT;

ANIMALS; BILE ACIDS AND SALTS; CELL LINE; COMPUTER SIMULATION; DOGS; GLUTAMIC ACID; HUMANS; KIDNEY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANIC ANION TRANSPORTERS, SODIUM-DEPENDENT; PIPERIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; SYMPORTERS;

EID: 67349278539     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-009-9877-3     Document Type: Article

References (45)

1. MV St-Pierre GA Kullak-Ublick B Hagenbuch PJ Meier 2001 Transport of bile acids in hepatic and non-hepatic tissues J Exp Biol 204 1673 86
2. F Gilardi N Mitro C Godio E Scotti D Caruso M Crestani E De Fabiani 2007 The pharmacological exploitation of cholesterol 7alpha-hydroxylase, the key enzyme in bile acid synthesis: from binding resins to chromatin remodelling to reduce plasma cholesterol Pharmacol Ther 116 449 72
3. C Pauli-Magnus B Stieger Y Meier GA Kullak-Ublick PJ Meier 2005 Enterohepatic transport of bile salts and genetics of cholestasis J Hepatol 43 342 57
4. E Sievanen 2007 Exploitation of bile acid transport systems in prodrug design Molecules 12 1859 89
5. MH Wong P Oelkers AL Craddock PA Dawson 1994 Expression cloning and characterization of the hamster ileal sodium-dependent bile acid transporter J Biol Chem 269 1340 7
6. EY Zhang MA Phelps A Banerjee CM Khantwal C Chang F Helsper PW Swaan 2004 Topology scanning and putative three-dimensional structure of the extracellular binding domains of the apical sodium-dependent bile acid transporter (SLC10A2) Biochemistry 43 11380 92
7. A Balakrishnan SA Wring JE Polli 2006 Interaction of native bile acids with human apical sodium-dependent bile acid transporter (hASBT): influence of steroidal hydroxylation pattern and C-24 conjugation Pharm Res 23 1451 9
8. KH Baringhaus H Matter S Stengelin W Kramer 1999 Substrate specificity of the ileal and the hepatic Na+/bile acid cotransporters of the rabbit. II. A reliable 3D QSAR pharmacophore model for the ileal Na+/bile acid cotransporter J Lipid Res 40 2158 68
9. AL Craddock MW Love RW Daniel LC Kirby HC Walters MH Wong PA Dawson 1998 Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter Am J Physiol 274 G157 69
10. L Lack IM Weiner 1966 Intestinal bile salt transport: structure-activity relationships and other properties Am J Physiol 210 1142 52
11. A Braun A Yesilaltay S Acton KO Broschat ES Krul N Napawan N Stagliano M Krieger 2008 Inhibition of intestinal absorption of cholesterol by ezetimibe or bile acids by SC-435 alters lipoprotein metabolism and extends the lifespan of SR-BI/apoE double knockout mice Atherosclerosis 198 77 84
12. SJ Tremont LF Lee HC Huang BT Keller SC Banerjee SR Both AJ Carpenter CC Wang DJ Garland W Huang C Jones KJ Koeller SA Kolodziej J Li RE Manning MW Mahoney RE Miller DA Mischke NP Rath T Fletcher EJ Reinhard MB Tollefson WF Vernier GM Wagner SR Rapp J Beaudry K Glenn K Regina JR Schuh ME Smith JS Trivedi DB Reitz 2005 Discovery of potent, nonsystemic apical sodium-codependent bile acid transporter inhibitors (Part 1) J Med Chem 48 5837 52
13. M Vicens RI Macias O Briz A Rodriguez MY El-Mir M Medarde JJ Marin 2007 Inhibition of the intestinal absorption of bile acids using cationic derivatives: mechanism and repercussions Biochem Pharmacol 73 394 404
14. M Vicens M Medarde RI Macias MG Larena A Villafaina MA Serrano JJ Marin 2007 Novel cationic and neutral glycocholic acid and polyamine conjugates able to inhibit transporters involved in hepatic and intestinal bile acid uptake Bioorg Med Chem 15 2359 67
15. KL West TL Zern DN Butteiger BT Keller ML Fernandez 2003 SC-435, an ileal apical sodium co-dependent bile acid transporter (ASBT) inhibitor lowers plasma cholesterol and reduces atherosclerosis in guinea pigs Atherosclerosis 171 201 10
16. Aa Balakrishnan JE Polli 2006 Apical sodium dependent bile acid transporter (ASBT, SLC10A2): a potential prodrug target Mol Pharm 3 223 30
17. A Balakrishnan SA Wring A Coop JE Polli 2006 Influence of charge and steric bulk in the C-24 region on the interaction of bile acids with human apical sodium-dependent bile acid transporter Mol Pharm 3 282 92
18. D Bernard A Coop AD MacKerell Jr 2003 2D conformationally sampled pharmacophore: a ligand-based pharmacophore to differentiate delta opioid agonists from antagonists J Am Chem Soc 125 3101 7
19. D Bernard A Coop AD MacKerell Jr 2007 Quantitative conformationally sampled pharmacophore for delta opioid ligands: reevaluation of hydrophobic moieties essential for biological activity J Med Chem 50 1799 809
20. D Bernard A Coop AD MacKerell Jr 2005 Conformationally sampled pharmacophore for peptidic delta opioid ligands J Med Chem 48 7773 80
21. G Han M Tamaki VJ Hruby 2001 Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group using HCl/dioxane (4 m) J Pept Res 58 338 41
22. S Chandrasekaran AF Kluge JA Edwards 1977 Studies in beta-lactams 6. Synthesis of substituted beta-lactams by addition of nitromethane to 6-oxopenicillanates and 7-oxocephalosporanates J Org Chem 42 3972 74
23. White E. Organic syntheses. Collective volume. New York: Wiley; 1973.
24. Bailey S, Gautier ECL, et al. Nicotinamide derivatives useful as PDF4 inhibitors. In U.S.P. Office (ed.), US Patent Application Publication, Pfizer Inc, USA; 2005. p. 56.
25. M Bruhaspathy S Bhattarcharyya J Williamson 2005 Chemoselective reductive alkylation of ammonia with carbonyl compounds: synthesis of primary and symmetrical secondary amines Tetrahedron 60 1463 71
26. A Balakrishnan DJ Sussman JE Polli 2005 Development of stably transfected monolayer overexpressing the human apical sodium-dependent bile acid transporter (hASBT) Pharm Res 22 1269 80
27. P Gonzalez JE Polli 2008 Impact of impurity on kinetic estimates from transport and inhibition studies J Pharmacol Exp Ther 326 296 305
28. A Balakrishnan N Hussainzada P Gonzalez M Bermejo PW Swaan JE Polli 2007 Bias in estimation of transporter kinetic parameters from overexpression systems: Interplay of transporter expression level and substrate affinity J Pharmacol Exp Ther 320 133 44
29. BR Brooks RE Bruccoleri BD Olafson DJ States S Swaminathan M Karplus 1983 CHARMM: A program for macromolecular energy, minimization, and dynamics calculations J Comput Chem 4 187 217
30. M Feig J Karanicolas CL Brooks 3rd 2004 MMTSB Tool Set: enhanced sampling and multiscale modeling methods for applications in structural biology J Mol Graph Model 22 377 95
31. AE García KY Sanbonmatsu 2001 Exploring the energy landscape of a beta hairpin in explicit solvent Proteins Struct Funct Bioinform 42 3 345 354
32. Y Sugita Y Okamoto 1999 Replica-exchange molecular dynamics method for protein folding Chem Phys Lett 314 141 51
33. Allen MP, Tildesley DJ. Computer simulation of liquids. Oxford: Clarendon; 1987.
34. MS Lee M Feig FR Salsbury CL Brooks 2003 New analytic approximation to the standard molecular volume definition and its application to generalized born calculations J Comput Chem 24 1348 56
35. MS Lee FR Salsbury CL Brooks 2002 Novel generalized Born methods J Chem Phys 116 10606 14
36. JP Ryckaert G Ciccotti JC Berendsen 1977 Numerical integration of the cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes J Comput Phys 23 327 41
37. B Lee FM Richards 1971 The interpretation of protein structures: estimation of static accessibility J Mol Biol 55 379 400
38. C Chothia 1975 Structural invariants in protein folding Nature 254 304 8
39. Chemical Computing Group. Molecular Operating Environment. Montreal, Quebec, Canada, http://www.chemcomp.com (2009).
40. B Reiser D Faraggi 1999 Confidence intervals for the overlapping coefficient: the normal equal variance case Statistician 48 413 8
41. H Akaike 1981 Likeliood of a model and information criteria J Econom 16 3 14
42. McQuarrie ADR, Tsai CL. Regression and time series model selection. Singapore: World Scientific; 1998.
43. ST Buckland KP Burnham NH Augustin 1997 Model selection: An integral part of inference Biometrics 53 603 18
44. S Ekins L Mirny EG Schuetz 2002 A ligand-based approach to understanding selectivity of nuclear hormone receptors PXR, CAR, FXR, LXRα, and LXRβ Pharm Res 19 1788 800
45. DJ Barlow JM Thornton 1983 Ion-pairs in proteins J Mol Biol 168 867 85