Polymeric bile acid sequestrants—Synthesis using conventional methods and new approaches based on “controlled”/living radical polymerization

Dhal, 2006, Polymers as drugs, 9 Duncan, 2003, The dawning era of polymer therapeutics, Nature Reviews Drug Discovery, 2, 347, 10.1038/nrd1088 Dhal, 2005, Functional polymers as human therapeutic agents, Industrial and Engineering Chemistry Research, 44, 8593, 10.1021/ie040290i Dhal, 2009, Functional polymers as therapeutic agents: concept to market place, Advanced Drug Delivery Reviews, 61, 1121, 10.1016/j.addr.2009.05.004 Liu, 2009, Polymer-based therapeutics, Macromolecules, 42, 3, 10.1021/ma801782q Dhal, 2007, Biologically active polymeric sequestrants: design, synthesis, and therapeutic applications, Pure and Applied Chemistry, 79, 1521, 10.1351/pac200779091521 Barker, 2006, Review article: tolevamer, a novel toxin-binding polymer: overview of preclinical pharmacology and physicochemical properties, Alimentary Pharmacology & Therapeutics, 24, 1525, 10.1111/j.1365-2036.2006.03157.x Excellence SNIHC, 2008 Reiner Ž, 2011, ESC/EAS Guidelines for the management of dyslipidaemias, European Heart Journal, 32, 1769, 10.1093/eurheartj/ehr158 Hou, 2009, Lowering low-density lipoprotein cholesterol: statins, ezetimibe, bile acid sequestrants, and combinations: comparative efficacy and safety, Endocrinology and Metabolism Clinics of North America, 38, 79, 10.1016/j.ecl.2008.11.007 Staels, 2009, Bile acids and metabolic regulation, Diabetes Care, 32, S237, 10.2337/dc09-S355 Einarsson, 1991, Bile acid sequestrants: mechanisms of action on bile acid and cholesterol metabolism, European Journal of Clinical Pharmacology, 40, S53, 10.1007/BF03216291 Staels, 2010, Bile acid sequestrants for lipid and glucose control, Current Diabetes Reports, 10, 70, 10.1007/s11892-009-0087-5 Lee, 2002, Synthesis of cationic polysaccharide derivatives and their hypocholesterolaemic capacity, Biotechnology and Applied Biochemistry, 35, 181, 10.1042/BA20010088 Zarras, 1999, Polycationic salts as bile acid sequestering agents, Progress in Polymer Science, 24, 485, 10.1016/S0079-6700(99)00002-7 Swaan, 1996, Use of the intestinal and hepatic bile acid transporters for drug delivery, Advanced Drug Delivery Reviews, 20, 59, 10.1016/0169-409X(95)00130-Y Insull, 2006, Clinical utility of bile acid sequestrants in the treatment of dyslipidemia: a scientific review, Southern Medical Journal, 99, 257, 10.1097/01.smj.0000208120.73327.db Mandeville, 1997, The sequestration of bile acids, a non-absorbed method for cholesterol reduction. A review, Current Pharmaceutical Design, 3, 15, 10.2174/138161280301221005123941 Huval, 2004, Syntheses of hydrophobically modified cationic hydrogels by copolymerization of alkyl substituted diallylamine monomers and their use as bile acid sequestrants, European Polymer Journal, 40, 693, 10.1016/j.eurpolymj.2003.11.012 Gore MA, Kulkarni MGK. Bile acid sequestrants and process for preparation therefor. US Patent 0122375, Council of Scientific and Industrial Research; 2007. Mandeville WH, Holmes-Farley SR. Process for removing bile salts from a patient and alkylated compositions therefor. WO 95/34585, Geltex Pharmaceuticals; 1995. Holmes-Farley SR, Mandeville WH, Burke SK, Goldberg DI. Method for treating hypercholesterolemia with polyallylamine polymers. US Patent 6,423,754, Geltex Pharmaceuticals; 2002. Holmes-Farley SR, Dhal PK, Petersen JS. Poly-(diallylamine)-based bile acid sequestrants. US Patent 7,125,547, Genzyme Corporation; 2006. Anonymous. Drugs@FDA: FDA approved drug products. http://www.accessdata.fda.gov/scripts/cder/drugsatfda; 2011 [accessed Sep 2012]. Asami, 2002, Treatment of children with familial hypercholesterolemia with colestilan, a newly developed bile acid-binding resin, Atherosclerosis, 164, 381, 10.1016/S0021-9150(02)00047-3 2011, 4160 Nichifor, 2001, Bile acid sequestrants based on cationic dextran hydrogel microspheres. 2. Influence of the length of alkyl substituents at the amino groups of the sorbents on the sorption of bile salts, Journal of Pharmaceutical Sciences, 90, 681, 10.1002/jps.1024 Primack, 1977, Hyperchloremia and hypernatremia associated with cholestyramine therapy, Pediatric Research, 11, 520, 10.1203/00006450-197704000-00902 Harrold, 2007, Antihyperlipoproteinemics and inhibitors of cholesterol biosynthesis, 797 Honda, 2000, Studies on adsorption characteristics of bile acids and methotrexate to a new type of anion-exchange resin, colestimide, Chemical and Pharmaceutical Bulletin, 48, 978, 10.1248/cpb.48.978 Benson, 1993, Invitro studies to investigate the reasons for the low potency of cholestyramine and colestipol, Journal of Pharmaceutical Sciences, 82, 80, 10.1002/jps.2600820118 Pollex, 2008, Emerging antidyslipidemic drugs, Expert Opinion on Emerging Drugs, 13, 363, 10.1517/14728214.13.2.363 Alberto, 2009, Colesevelam hydrochloride: usefulness of a specifically engineered bile acid sequestrant for lowering LDL-cholesterol, European Journal of Preventive Cardiology, 16, 1, 10.1097/HJR.0b013e32831215db Davidson, 1999, Colesevelam hydrochloride (cholestagel): a new, potent bile acid sequestrant associated with a low incidence of gastrointestinal side effects, Archives of Internal Medicine, 159, 1893, 10.1001/archinte.159.16.1893 Steinmetz, 2002, Colesevelam hydrochloride, American Journal of Health-System Pharmacy, 59, 932, 10.1093/ajhp/59.10.932 Matsuzaki, 2002, Colestimide: the efficacy of a novel anion-exchange resin in cholestatic disorders, Journal of Gastroenterology and Hepatology, 17, 1133, 10.1046/j.1440-1746.2002.02860.x Wu, 1996, Polymeric sorbents for bile acids. 5. Polyacrylamide resins with ammonium-containing pendants, Langmuir, 12, 466, 10.1021/la9500641 Huval, 2004, Ammonium and guanidinium functionalized hydrogels as bile acid sequestrants: synthesis, characterization, and biological properties, Journal of Macromolecular Science, Part A. Pure and Applied Chemistry, 41, 231, 10.1081/MA-120028203 Nichifor, 2001, Interaction of hydrophobically modified cationic dextran hydrogels with biological surfactants, Journal of Physical Chemistry B, 105, 2314, 10.1021/jp002621k Cameron, 2002, Amphiphilic block copolymers as bile acid sorbents: 2. Polystyrene-b-poly(N,N,N-trimethylammoniumethylene acrylamide chloride): self-assembly and application to serum cholesterol reduction, Biomacromolecules, 3, 124, 10.1021/bm015596c Anderson, 2009, Health benefits of dietary fiber, Nutrition Reviews, 67, 188, 10.1111/j.1753-4887.2009.00189.x Brownlee, 2011, The physiological roles of dietary fibre, Food Hydrocolloids, 25, 238, 10.1016/j.foodhyd.2009.11.013 Chau, 2004, Investigation of the cholesterol-lowering action of insoluble fibre derived from the peel of Citrus sinensis L. cv. Liucheng, Food Chemistry, 87, 361, 10.1016/j.foodchem.2003.12.006 Eastwood, 1968, Studies on the adsorption of bile salts to non-absorbed components of diet, Biochimica et Biophysica Acta (BBA) – Lipids and Lipid Metabolism, 152, 165, 10.1016/0005-2760(68)90018-0 Elhardallou, 1992, The bile acids binding of the fibre-rich fractions of three starchy legumes, Plant Foods for Human Nutrition (Formerly Qualitas Plantarum), 42, 207, 10.1007/BF02193928 Hoagland, 1989, Binding of dietary anions to vegetable fiber, Journal of Agricultural and Food Chemistry, 37, 1343, 10.1021/jf00089a030 Kritchesvsky, 1995, In vitro binding properties of dietary fibre, European Journal of Clinical Nutrition, 49, 113 Buhman, 1998, Dietary psyllium increases fecal bile acid excretion, total steroid excretion and bile acid biosynthesis in rats, Journal of Nutrition, 128, 1199, 10.1093/jn/128.7.1199 Garcia-Diez, 1996, Pectin feeding influences fecal bile acid excretion, hepatic bile acid and cholesterol synthesis and serum cholesterol in rats, Journal of Nutrition, 126, 1766 Kritchevsky, 2005, Influence of a fiber mixture on serum and liver lipids and on fecal fat excretion in rats, Nutrition Research, 25, 485, 10.1016/j.nutres.2005.02.001 Jenkins, 2000, Viscous fibers, health claims, and strategies to reduce cardiovascular disease risk, American Journal of Clinical Nutrition, 71, 401, 10.1093/ajcn/71.2.401 Kendall, 2010, The link between dietary fibre and human health, Food Hydrocolloids, 24, 42, 10.1016/j.foodhyd.2009.08.002 Brown, 1999, Cholesterol-lowering effects of dietary fiber: a meta-analysis, American Journal of Clinical Nutrition, 69, 30, 10.1093/ajcn/69.1.30 Van Rosendaal, 2004, Effect of time of administration on cholesterol-lowering by psyllium: a randomized cross-over study in normocholesterolemic or slightly hypercholesterolemic subjects, Nutrition Journal, 3, 10.1186/1475-2891-3-17 Camire, 2002, Raisin dietary fiber composition and in vitro bile acid binding, Journal of Agricultural and Food Chemistry, 51, 834, 10.1021/jf025923n Kahlon, 2007, In vitro binding of bile acids by bananas, peaches, pineapple, grapes, pears, apricots and nectarines, Food Chemistry, 101, 1046, 10.1016/j.foodchem.2006.02.059 Kahlon, 2002, In vitro binding of bile acids by soy protein, pinto beans, black beans and wheat gluten, Food Chemistry, 79, 425, 10.1016/S0308-8146(02)00192-9 Kongo-Dia-Moukala, 2011, In vitro binding capacity of bile acids by defatted corn protein hydrolysate, International Journal of Molecular Sciences, 12, 1066, 10.3390/ijms12021066 Dongowski, 2007, Interactions between dietary fibre-rich preparations and glycoconjugated bile acids in vitro, Food Chemistry, 104, 390, 10.1016/j.foodchem.2006.11.053 Cornfine, 2010, Influence of chemical and physical modification on the bile acid binding capacity of dietary fibre from lupins (Lupinus angustifolius L.), Food Chemistry, 122, 638, 10.1016/j.foodchem.2010.03.024 Kahlon, 2007, Steam cooking significantly improves in vitro bile acid binding of beets, eggplant, asparagus, carrots, green beans, and cauliflower, Nutrition Research, 27, 750, 10.1016/j.nutres.2007.09.011 Kahlon, 2008, Steam cooking significantly improves in vitro bile acid binding of collard greens, kale, mustard greens, broccoli, green bell pepper, and cabbage, Nutrition Research, 28, 351, 10.1016/j.nutres.2008.03.007 Zacheri, 2011, In vitro model to correlate viscosity and bile acid-binding capacity of digested water-soluble and insoluble dietary fibres, Food Chemistry, 126, 423, 10.1016/j.foodchem.2010.10.113 Cohn, 2010, Reduction in intestinal cholesterol absorption by various food components: Mechanisms and implications, Atherosclerosis Supplements, 11, 45, 10.1016/j.atherosclerosissup.2010.04.004 Férézou, 1997, Hypocholesterolemic action of beta-cyclodextrin and its effects on cholesterol metabolism in pigs fed a cholesterol-enriched diet, Journal of Lipid Research, 38, 86, 10.1016/S0022-2275(20)37278-3 Riottot, 1993, Hypolipidemic effects of β-cyclodextrin in the hamster and in the genetically hypercholesterolemic rico rat, Lipids, 28, 181, 10.1007/BF02536637 Trautwein, 1999, Impact of beta-cyclodextrin and resistant starch on bile acid metabolism and fecal steroid excretion in regard to their hypolipidemic action in hamsters, Biochimica et Biophysica Acta (BBA) – Molecular and Cell Biology of Lipids, 1437, 1, 10.1016/S0005-2760(98)00174-X Baille, 2000, Functionalized beta-cyclodextrin polymers for the sorption of bile salts, Journal of Macromolecular Science, Part A. Pure and Applied Chemistry, 37, 677, 10.1081/MA-100101117 Nichifor, 2000, Sodium cholate sorption on cationic dextran hydrogel microspheres. 1. Influence of the chemical structure of functional groups, International Journal of Biological Macromolecules, 28, 15, 10.1016/S0141-8130(00)00145-8 Nichifor, 1998, Aminated polysaccharides as bile acid sorbents: in vitro study, Journal of Biomaterials Science Polymer Edition, 9, 519, 10.1163/156856298X00019 Gallaher, 2000, Cholesterol reduction by glucomannan and chitosan is mediated by changes in cholesterol absorption and bile acid and fat excretion in rats, Journal of Nutrition, 130, 2753, 10.1093/jn/130.11.2753 Hirano, 1990, Chitosan as an ingredient for domestic animal feeds, Journal of Agricultural and Food Chemistry, 38, 1214, 10.1021/jf00095a012 Sugano, 1988, Hypocholesterolemic action of chitosans with different viscosity in rats, Lipids, 23, 187, 10.1007/BF02535456 Trautwein, 1997, Cholesterol-lowering and gallstone-preventing action of chitosans with different degrees of deacetylation in hamsters fed cholesterol-rich diets, Nutrition Research, 17, 1053, 10.1016/S0271-5317(97)00069-9 Zhou, 2006, In vitro binding of bile acids and triglycerides by selected chitosan preparations and their physico-chemical properties, LWT-Food Science and Technology, 39, 1087, 10.1016/j.lwt.2005.07.009 Ikeda, 1993, Effects of chitosan hydrolyzates on lipid absorption and on serum and liver lipid concentration in rats, Journal of Agricultural and Food Chemistry, 41, 431, 10.1021/jf00027a016 Lee, 1999, Modification of chitosan to improve its hypocholesterolemic capacity, Bioscience, Biotechnology, and Biochemistry, 63, 833, 10.1271/bbb.63.833 Murata, 2009, Properties of an oral preparation containing a chitosan salt, Molecules, 14, 755, 10.3390/molecules14020755 Kim, 1999, A synthesis of O-diethylaminoethyl chitosan and its binding ability of cholate and deoxycholate anion in vitro, Polymer Bulletin, 42, 25, 10.1007/s002890050430 Murata, 2006, Adsorption of bile acid by chitosan salts prepared with cinnamic acid and analogue compounds, Journal of Biomaterials Science Polymer Edition, 17, 781, 10.1163/156856206777656517 Huval, 2001, Novel cholesterol lowering polymeric drugs obtained by molecular imprinting, Macromolecules, 34, 1548, 10.1021/ma001898f Zhang, 2000, Enhancing the “stickiness” of bile acids to cross-linked polymers: a bioconjugate approach to the design of bile acid sequestrants, Bioconjugate Chemistry, 11, 397, 10.1021/bc990151v Figuly, 1997, Preparation and characterization of novel poly(alkylamine)-based hydrogels designed for use as bile acid sequestrants, Macromolecules, 30, 6174, 10.1021/ma9702509 Zhu, 2002, Polymeric materials containing bile acids, Accounts of Chemical Research, 35, 539, 10.1021/ar0101180 Cameron, 2002, Amphiphilic block copolymers as bile acid sorbents: 1. Synthesis of polystyrene-b-poly(N,N,N-trimethylammoniumethylene acrylamide chloride), Biomacromolecules, 3, 116, 10.1021/bm015595k Huval, 2001, Amine functionalized polyethers as bile acid sequestrants: synthesis and biological evaluation, Journal of Macromolecular Science, Part A. Pure and Applied Chemistry, 38, 1559, 10.1081/MA-100108405 Huval, 2004, Molecularly imprinted bile acid sequestrants: synthesis and biological studies, 85 Wang, 2007, Specific binding of cholic acid by cross-linked polymers prepared by the hybrid imprinting method, Polymer, 48, 5565, 10.1016/j.polymer.2007.07.003 Yanez, 2010, Computational modeling and molecular imprinting for the development of acrylic polymers with high affinity for bile salts, Analytica Chimica Acta, 659, 178, 10.1016/j.aca.2009.11.054 Bergmann, 2008, Molecularly imprinted polymers with specific recognition for macromolecules and proteins, Progress in Polymer Science, 33, 271, 10.1016/j.progpolymsci.2007.09.004 Hillberg, 2008, Biomolecule imprinting: developments in mimicking dynamic natural recognition systems, IRBM, 29, 89, 10.1016/j.rbmret.2007.11.023 Byrne, 2008, Molecular imprinting within hydrogels. II: progress and analysis of the field, International Journal of Pharmaceutics, 364, 188, 10.1016/j.ijpharm.2008.09.002 Komiyama, 2004 Wang, 2011, Affinity-based drug delivery, Macromolecular Bioscience, 11, 321, 10.1002/mabi.201000206 Gao, 2009, Synthesis of functional polymers with controlled architecture by CRP of monomers in the presence of cross-linkers: from stars to gels, Progress in Polymer Science, 34, 317, 10.1016/j.progpolymsci.2009.01.001 Matyjaszewski, 2012, Atom Transfer radical polymerization (ATRP): current status and future perspectives, Macromolecules, 45, 4015, 10.1021/ma3001719 Moad, 2008, Toward living radical polymerization, Accounts of Chemical Research, 41, 1133, 10.1021/ar800075n Matyjaszewski, 2002, General concepts and history of living radical polymerization, 361 Braunecker, 2007, Controlled/living radical polymerization: features, developments, and perspectives, Progress in Polymer Science, 32, 93, 10.1016/j.progpolymsci.2006.11.002 Boyer, 2009, Bioapplications of RAFT polymerization, Chemical Reviews, 109, 5402, 10.1021/cr9001403 Xu, 2009, Bioactive surfaces and biomaterials via atom transfer radical polymerization, Progress in Polymer Science, 34, 719, 10.1016/j.progpolymsci.2009.04.005 Uhrig, 2011, Synthesis of well-defined multigraft copolymers, Polymer Chemistry, 2, 69, 10.1039/C0PY00185F Postma, 2006, Synthesis of well-defined polystyrene with primary amine end groups through the use of phthalimido-functional RAFT agents, Macromolecules, 39, 5293, 10.1021/ma060245h Toquer, 2007, Synthesis via ATRP and anchoring properties of ammonium-terminated monofunctional or telechelic polystyrenes, Macromolecular Chemistry and Physics, 208, 94, 10.1002/macp.200600475 Grassl, 2008, Nitroxide-mediated radical polymerization of acrylamide in water solution, European Polymer Journal, 44, 50, 10.1016/j.eurpolymj.2007.10.019 Rodriguez-Emmenegger, 2011, Low temperature aqueous living/controlled (RAFT) polymerization of carboxybetaine methacrylamide up to high molecular weights, Macromolecular Rapid Communications, 32, 958, 10.1002/marc.201100176 Coelho, 2008, Synthesis of poly(ethyl acrylate) by single electron transfer-degenerative chain transfer living radical polymerization in water catalyzed by Na2S2O4, Journal of Macromolecular Science, Part A. Pure and Applied Chemistry, 46, 421, 10.1002/pola.23548 Coelho, 2009, Synthesis of poly(2-methoxyethyl acrylate) by single electron transfer-degenerative transfer living radical polymerization catalyzed by Na2S2O4 in water, Journal of Macromolecular Science, Part A. Pure and Applied Chemistry, 47, 4454, 10.1002/pola.21389 Coelho, 2006, Single electron transfer-degenerative chain transfer living radical polymerization of N-butyl acrylate catalyzed by Na2S2O4 in water media, Journal of Macromolecular Science, Part A. Pure and Applied Chemistry, 44, 2809, 10.1002/pola.23698 Ding, 2009, Comparison of surface confined ATRP and SET-LRP syntheses for a series of amino (meth)acrylate polymer brushes on silicon substrates, Journal of Macromolecular Science, Part A. Pure and Applied Chemistry, 47, 6552 Hao, 2006, Preparation of a comb-shaped cholic acid-containing polymer by atom transfer radical polymerization, Biomacromolecules, 7, 995, 10.1002/pola.24291 Hossain, 2010, Facile synthesis of core-surface crosslinked nanoparticles by interblock RAFT polymerization, Journal of Macromolecular Science, Part A. Pure and Applied Chemistry, 48, 4958 Destarac, 2010, Controlled radical polymerization: industrial stakes, obstacles and achievements, Macromolecular Reaction Engineering, 4, 165, 10.1002/mren.200900087