Biodegradable polyglycerols with randomly distributed ketal groups as multi-functional drug delivery systems

Biomaterials

Volumn 34, Issue 25, 2013, Pages 6068-6081

  Shenoi, Rajesh A ^a   Lai, Benjamin F L ^a   Imran Ul Haq, Muhammad ^a   Brooks, Donald E ^a   Kizhakkedathu, Jayachandran N ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Biocompatibility; Biodegradable polyglycerols; Invivo degradation; Ketal groups; Multifunctional nanostructures; PH dependent hydrolysis

Indexed keywords

IN-VIVO; KETAL GROUPS; MULTIFUNCTIONAL NANOSTRUCTURES; PH-DEPENDENT; POLYGLYCEROLS;

BIOCOMPATIBILITY; BIODEGRADATION; DEGRADATION; DENDRIMERS; DRUG DELIVERY; FUNCTIONAL POLYMERS; GEL PERMEATION CHROMATOGRAPHY; HYDROLYSIS; MEDICAL APPLICATIONS; NANOSTRUCTURES; PHYSIOLOGICAL MODELS; PHYSIOLOGY; POLYMER BLENDS; TISSUE; TISSUE ENGINEERING;

MOLECULAR WEIGHT;

ACETAL DERIVATIVE; BUFFER; EPOXIDE; GLYCEROL DERIVATIVE; GLYCIDOL; MONOMER; TRITIUM;

ANIMAL EXPERIMENT; ARTICLE; BIOACCUMULATION; BIOCOMPATIBILITY; BIODEGRADATION; BLOOD COMPATIBILITY; CELL VIABILITY; CHEMICAL STRUCTURE; CIRCULATION; CONTROLLED STUDY; DEGRADATION; DRUG DELIVERY SYSTEM; FECES; FEMALE; GEL PERMEATION CHROMATOGRAPHY; HALF LIFE TIME; HISTOCOMPATIBILITY; HYDRODYNAMICS; HYDROLYSIS; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR WEIGHT; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PH; POLYMERIZATION; PRIORITY JOURNAL; RING OPENING; SYNTHESIS; TEMPERATURE;

ANIMALS; BIOCOMPATIBLE MATERIALS; CELL SURVIVAL; DRUG DELIVERY SYSTEMS; FEMALE; GLYCEROL; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; MICE; MICE, INBRED BALB C; POLYMERS;

MUS;

EID: 84878532612     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2013.04.043     Document Type: Article

References (54)

1. Ulery B.D., Nair L.S., Laurencin C.T. Biomedical applications of biodegradable polymers. JPolym Sci Part B Polym Phys 2011, 49:832-864.
2. Uhrich K.E., Cannizzaro S.M., Langer R.S., Shakesheff K.M. Polymeric systems for controlled drug release. Chem Rev 1999, 99:3181-3198.
3. Kumar N., Langer R.S., Domb A.J. Polyanhydrides: an overview. Adv Drug Deliv Rev 2002, 54:889-910.
4. Heller J., Barr J., Ng S.Y., Abdellauoi K.S., Gurny R. Poly (ortho esters): synthesis, characterization, properties and uses. Adv Drug Deliv Rev 2002, 54:1015-1039.
5. Domb A.J., Kumar N., Ezra A. Biodegradable polymers in clinical use and clinical development 2011, John Wiley & Sons, Inc.
6. Armentano I., Dottori M., Fortunati E., Mattioli S., Kenny J.M. Biodegradable polymer matrix composites for tissue engineering. Polym Degrad Stab 2010, 95:2126-2146.
7. Fu K., Pack D.W., Klibanov A.M., Langer R. Visual evidence of acidic environment within degrading poly(lactic-co-glycolic acid) (PLGA) microspheres. Pharm Res 2000, 17:100-106.
8. Roux E., Francis M., Winnik F.M., Leroux J.C. Polymer based pH-sensitive carriers as a means to improve the cytoplasmic delivery of drugs. Int J Pharm 2002, 242:25-36.
9. Ubrich K., Subr V. Polymeric anticancer drugs with pH-controlled activation. Adv Drug Deliv Rev 2004, 56:1023-1050.
10. Kwon Y.J. Before and after endosomal escape: roles of stimuli-converting siRNA/polymer interactions in determining gene silencing efficiency. Acc Chem Res 2012, 45:1077-1088.
11. Morinaga H., Morikawa H., Wang Y., Sudo A., Endo T. Amphiphilic copolymer having acid-labile acetal in the side chain as a hydrophobe: controlled release of aldehyde by thermoresponsive aggregation-dissociation of polymeric micelles. Macromolecules 2009, 42:2229-2235.
12. Tomlinson R., Heller J., Brocchini S., Duncan R. Polyacetal-doxorubicin conjugates designed for pH dependent degradation. Bioconjug Chem 2003, 14:1096-1106.
13. Tomlinson R., Klee M., Garrett S., Heller J., Duncan R., Brocchini S. Pendant chain functionalized polyacetals that display pH-dependent degradation: a platform for the development of novel polymer therapeutics. Macromolecules 2002, 35:473-480.
14. Wang Y., Morinaga H., Sudo A., Endo T. Synthesis of amphiphilic polyacetal by polycondensation of aldehyde and polyethylene glycol as an acid-labile polymer for controlled release of aldehyde. JPolym Sci Part A Polym Chem 2011, 49:596-602.
15. Dingels C., Muller S., Steinbach T., Tonhauser C., Frey H. Universal concept for the implementation of single cleavable unit at tunable position in functional poly(ethylene glycol)s. Biomacromolecules 2012, ASAP article. 10.1021/bm3016797.
16. Chatterjee S., Ramakrishnan S. Hyperbranched polyacetals with tunable degradation rates. Macromolecules 2011, 44:4658-4664.
17. Heffernan M.J., Murthy N. Polyketal nanoparticles: a new pH-sensitive biodegradable drug delivery vehicle. Bioconjug Chem 2005, 16:1340-1342.
18. Lee S., Yang S.C., Heffernan M.J., Taylor W.R., Murthy N. Polyketal microparticles: a new delivery vehicle for superoxide dismutase. Bioconjug Chem 2007, 18:4-7.
19. Yang S.C., Bhide M., Crispe I.N., Pierce R.H., Murthy N. Polyketal copolymers: a new acid-sensitive delivery vehicle for treating acute inflammatory diseases. Bioconjug Chem 2008, 19:1164-1169.
20. Sy J.C., Seshadri G., Yang S.C., Brown M., Oh T., Dikalov S., et al. Sustained release of a p38 inhibitor from non-inflammatory microspheres inhibits cardiac dysfunction. Nat Mater 2008, 7:863-869.
21. Fiore V.F., Lofton M.C., Roser-Page S., Yang S.C., Roman J., Murthy N., et al. Polyketal microparticles for therapeutic delivery to the lung. Biomaterials 2010, 31:810-817.
22. + T-cells by dendritic cells pulsed with polyketal microparticles containing ion-paired protein antigen and poly(inosinic acid) and poly(cytidylic acid). Biomaterials 2009, 30:910-918.
23. Seshadri G., Sy J.C., Brown M., Dikalov S., Yang S.C., Murthy N., et al. The delivery of superoxide dismutase encapsulated in polyketal microparticles to rat myocardium and protection from myocardial ischemia-reperfusion injury. Biomaterials 2010, 31:1372-1379.
24. Jain R., Standley S.M., Frechet J.M.J. Synthesis and degradation of pH-sensitive linear poly (amidoamine)s. Macromolecules 2007, 40:452-457.
25. Bachelder E.M., Baudette T.T., Broaders K.E., Paramonov S.E., Dashe J., Frechet J.M.J. Acid-degradable polyurethane particles for protein-based vaccines: biological evaluation and invitro analysis of particle degradation products. Mol Pharm 2008, 5:876-884.
26. Cohen J.L., Almutairi A., Cohen J.A., Bernstein M., Brody S.L., Schuster D.P., et al. Enhanced cell penetration of acid-degradable particles functionalized with cell-penetrating peptides. Bioconjug Chem 2008, 19:876-881.
27. Broaders K.E., Cohen J.A., Beaudette T.T., Bachelder E.M., Frechet J.M.J. Acetalated dextran is a chemically and biologically tunable material for particulate immunotherapy. Proc Natl Acad Sci U S A 2009, 106:5497-5502.
28. Shenoi R.A., Narayanannair J.K., Hamilton J.H., Lai B.F.L., Horte S., Kainthan R.K., et al. Branched multifunctional polyether polyketals: variation of ketal group structure enables unprecedented control over polymer degradation in solution and within cells. JAm Chem Soc 2012, 134:14945-14957.
29. Calderon M., Quadir M.A., Sharma S.K., Haag R. Dendritic polyglycerols for biomedical applications. Adv Mater 2010, 22:190-218.
30. Wilms D., Striba S.E., Frey H. Hyperbranched polyglycerols: from the controlled synthesis of biocompatible polyether polyols to multipurpose applications. Acc Chem Res 2010, 43:129-141.
31. Kainthan R.K., Muliawan E.B., Hatzikiriakos S.G., Brooks D.E. Synthesis, characterization and viscoelastic properties of high molecular weight hyperbranched polyglycerols. Macromolecules 2006, 39:7708-7717.
32. Wilms D., Wurm F., Nieberle J., Bohm P., Kemmer-Jonas U., Frey H. Hyperbranched polyglycerols with elevated molecular weights: a facile two-step synthesis protocol based on polyglycerol macroinitiators. Macromolecules 2009, 42:3230-3236.
33. Steinhilber D., Seiffer S., Heyman J.A., Paulus F., Weitz D.A., Haag R. Hyperbranched polyglycerols in the nanometer and micrometer scale. Biomaterials 2011, 32:1311-1316.
34. Rossi N.A.A., Constantinescu I., Brooks D.E., Scott M.D., Kizhakkedathu J.N. Enhanced cell surface polymer grafting in concentrated and nonreactive aqueous polymer solutions. JAm Chem Soc 2010, 132:3423-3430.
35. Turk H., Haag R., Alban S. Dendritic polyglycerol sulfates as new heparin analogues and potent inhibitors of the complement system. Bioconjug Chem 2004, 15:162-167.
36. Kizhakkedathu JN, Shenoi RA, Carter CJ, Brooks DE. Polymers for reversing heparin based anticoagulation. US Patent No. 0308546A1; 2012.
37. Mendelson A.A., Guan Q., Chafeeva I., da Roza G.A., Kizhakkedathu J.N., Du C. Hyperbranched polyglycerol is an efficacious and biocompatible novel osmotic agent in a rodent model of peritoneal dialysis. Perit Dial Int 2013, 33:15-27.
38. Kainthan R.K., Brooks D.E. Invivo biological evaluation of high molecular weight hyperbranched polyglycerols. Biomaterials 2007, 28:4779-4787.
39. Saatchi K., Gelder N., Gershkovich P., Sivak O., Wasan K.M., Kainthan R.K., et al. Long circulating non-toxic blood pool imaging agent based on hyperbranched polyglycerols. Int J Pharm 2012, 422:418-427.
40. Saatchi K., Soema P., Gelder N., Misri R., McPhee K., Baker J.H.E., et al. Hyperbranched polyglycerols as trimodal imaging agents: design, biocompatibility and tumor uptake. Bioconjug Chem 2012, 23:372-381.
41. Shenoi R.A., Lai B.F.L., Kizhakkedathu J.N. Synthesis, characterization and biocompatibility of biodegradable hyperbranched polyglycerols from acid-cleavable ketal group functionalized initiators. Biomacromolecules 2012, 13:3018-3030.
42. Tonhauser C., Schull C., Dingels C., Frey H. Branched acid-degradable, biocompatible polyether copolymers via anionic ring-opening polymerization using an epoxide inimer. ACS Macro Lett 2012, 1:1094-1097.
43. Hu M., Chen M., Li G., Pang Y., Wang D., Wu J., et al. Biodegradable hyperbranched polyglycerol with ester linkages for drug delivery. Biomacromolecules 2012, 13:3552-3561.
44. Sunder A., Hanselman R., Frey H., Mulhaupt R. Controlled synthesis of hyperbranched polyglycerols by ring- opening multibranching polymerization. Macromolecules 1999, 32:4240-4246.
45. Imran ul-haq M., Lai B.F.L., Chapanian R., Kizhakkedathu J.N. Influence of architecture of high molecular weight linear and hyperbranched polyglycerols on their biocompatibility and biodistribution. Biomaterials 2012, 33:9135-9147.
46. Deslongchamps P., Dory Y.L., Li S. The relative rate of hydrolysis of a series of acylic and six-membered cyclic acetals, ketals, orthoesters and orthocarbonates. Tetrahedron 2000, 56:3533-3537.
47. Gobert M.B., Sefton M.V. Biomaterial-associated thrombosis: roles of coagulation factors, complement, platelets and leukocytes. Biomaterials 2004, 25:5681-5703.
48. Kainthan R.K., Janzen J., Levin E., Devine D.V., Brooks D.E. Biocompatibility testing of branched and linear polyglycidol. Biomacromolecules 2006, 7:703-709.
49. Kainthan R.K., Hester S.R., Levin E., Devine D.V., Brooks D.E. Invitro biological evaluation of high molecular weight hyperbranched polyglycerols. Biomaterials 2007, 28:4581-4590.
50. Huang Y.C., Royappa A.T., Tundel S., Tsukamoto K., Sharma V. Biocompatibility of polyglycidol with human peripheral blood mononuclear cells. JAppl Polym Sci 2009, 111:2275-2278.
51. Inglis J.E., Radziwon K.A., Maniero G.D. The serum complement system: a simplified laboratory exercise to measure the activity of an important component of the immune system. Adv Physiol Educ 2008, 32:317-321.
52. Scott M.D., Murad K.L., Koumpouras F., Talbot M., Eaton J.W. Chemical camouflage of antigenic determinants: stealth erythrocytes. Proc Natl Acad Sci U S A 1997, 94:7566-7571.
53. Loubnan V., Nasser S.C. Aguide on intravenous drug compatibilities based on their pH. Pharm Glob (IJCP) 2010, 5:1-9.
54. Stranz M., Kastango E.S. Areview of pH and osmolarity. Int J Pharm Compd 2002, 6:216-220.