Prodrugs as self-assembled hydrogels: A new paradigm for biomaterials

Current Opinion in Biotechnology

Volumn 24, Issue 6, 2013, Pages 1174-1182

  Vemula, Praveen Kumar ^a,b   Wiradharma, Nikken ^c   Ankrum, James A ^c   Miranda, Oscar R ^c   John, George ^d   Karp, Jeffrey M ^c  

^a UNIVERSITY OF AGRICULTURAL SCIENCES   (India)

^b Department of Biotechnology   (India)

^c HARVARD MIT DIVISION OF HEALTH SCIENCES AND TECHNOLOGY   (United States)

^d CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILICS; CONTROLLED DRUG RELEASE; CONVENTIONAL DRUGS; DRUG LOADING; PRODRUGS; SELF-ASSEMBLED; STIMULI-RESPONSIVE DRUG DELIVERIES; TAILORED DEGRADATION;

BIOLOGICAL MATERIALS; DRUG DELIVERY; MEDICAL APPLICATIONS;

HYDROGELS;

AMPHOPHILE; AMYGDALIN; BENAZEPRIL; BIOMATERIAL; CELECOXIB; CURCUMIN; EXCIPIENT; FAMCICLOVIR; FOSPHENYTOIN SODIUM; GLUCOSAMINE; IBUPROFEN; OSELTAMIVIR; PACLITAXEL; PARACETAMOL; PARECOXIB; PIVAMPICILLIN; PRODRUG; VALACICLOVIR; VALGANCICLOVIR; VANCOMYCIN;

ANTINEOPLASTIC ACTIVITY; DRUG DELIVERY SYSTEM; DRUG DETERMINATION; DRUG RELEASE; DRUG SCREENING; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; ENCAPSULATION; ENZYMATIC DEGRADATION; HUMAN; HYDROGEL; HYDROPHOBICITY; IONIC STRENGTH; MOLECULAR INTERACTION; OSTEOARTHRITIS; PRIORITY JOURNAL; REVIEW; SCAR; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TISSUE ENGINEERING; WOUND;

BIOCOMPATIBLE MATERIALS; DRUG DELIVERY SYSTEMS; DRUG DESIGN; EXCIPIENTS; HUMANS; HYDROGELS; PRODRUGS; SOLUBILITY;

EID: 84887621286     PISSN: 09581669     EISSN: 18790429     Source Type: Journal    
DOI: 10.1016/j.copbio.2013.02.006     Document Type: Review

References (52)

1. DiMasi J.A., Feldman L., Seckler A., Wilson A. Trends in risks associated with new drug development: success rates for investigational drugs. Clin Pharmacol Ther 2008, 87:272-277.
2. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 2012, 64:4-17.
3. Ferrari M., Downing G. Medical nanotechnology: shortening clinical trials and regulatory pathways?. BioDrugs 2005, 19:203-210.
4. Beaumont K., Webster R., Gardner I., Dack K. Design of ester prodrugs to enhance oral absorption of poorly permeable compounds: challenges to the discovery scientist. Curr Drug Metab 2003, 4:461-485.
5. Kratz F., Muller I.A., Ryppa C., Warnecke A. Prodrug strategies in anticancer chemotherapy. ChemMedChem 2008, 3:20-53.
6. Mackman R.L., Cihlar T. Prodrug strategies in the design of nucleoside and nucleotide antiviral therapeutics. Annu Rep Med Chem 2004, 39:305-321.
7. Ettmayer P., Amidon G.L., Clement B., Testa B. Lessons learned from marketed and investigational prodrugs. J Med Chem 2004, 47:2393-2404.
8. Rautio J., Kumpulainen H., Heimbach T., Oliyai R., Oh D., Jarvinen T., Savolainen J. Prodrugs: design and clinical applications. Nat Rev Drug Discov 2008, 7:255-270.
9. ten Tije A.J., Verweij J., Loos W.J., Sparreboom A. Pharmacological effects of formulation vehicles: implications for cancer chemotherapy. Clin Pharmacokinet 2003, 42:665-685.
10. Weiss R.B., Donehower R.C., Wiernik P.H., Ohnuma T., Gralla R.J., Trump D.L., Baker J.R., Van Echo D.A., Von Hoff D.D., Leyland-Jones B. Hypersensitivity reactions from taxol. J Clin Oncol 1990, 8:1263-1268.
11. Kiyonaka S., Shinkai S., Hamachi I. Combinatorial library of low molecular-weight organo- and hydrogelators based on glycosylated amino acid derivatives by solid-phase synthesis. Chemistry 2003, 9:976-983.
12. de la Torre P.M., Torrado S. Interpolymer complexes of poly(acrylic acid) and chitosan: influence of the ionic hydrogel-forming medium. Biomaterials 2003, 24:1459-1468.
13. Kumashiro Y., Huh K.M., Ooya T., Yui N. Modulatory factors on temperature-synchronized degradation of dextran grafted with thermoresponsive polymers and their hydrogels. Biomacromolecules 2001, 2:874-879.
14. Slaughter B.V., Khurshid S.S., Fisher O.Z., Khademhosseini A., Peppas N.A. Hydrogels in regenerative medicine. Adv Mater 2009, 21:3307-3329.
15. Cui H., Webber M.J., Stupp S.I. Self-assembly of peptide amphiphiles: from molecules to nanostructures to biomaterials. Biopolymers 2010, 94:1-18.
16. Hartgerink J.D., Beniash E., Stupp S.I. Peptide-amphiphile nanofibers: a versatile scaffold for the preparation of self-assembling materials. Proc Natl Acad Sci U S A 2002, 99:5133-5138.
17. Silva G.A., Czeisler C., Niece K.L., Beniash E., Harrington D.A., Kessler J.A., Stupp S.I. Selective differentiation of neural progenitor cells by high-epitope density nanofibers. Science 2004, 303:1352-1355.
18. Zhang S., Holmes T.C., DiPersio C.M., Hynes R.O., Su X., Rich A. Self-complementary oligopeptide matrices support mammalian cell attachment. Biomaterials 1995, 16:1385-1393.
19. Patterson J., Hubbell J.A. Enhanced proteolytic degradation of molecularly engineered PEG hydrogels in response to MMP-1 and MMP-2. Biomaterials 2010, 30:7836-7845.
20. Haines-Butterick L., Rajagopal K., Branco M., Salick D., Rughani R., Pilarz M., Lamm M.S., Pochan D.J., Schneider J.P. Controlling hydrogelation kinetics by peptide design for three-dimensional encapsulation and injectable delivery of cells. Proc Natl Acad Sci U S A 2007, 104:7791-7796.
21. Branco M.C., Pochan D.J., Wagner N.J., Schneider J.P. Macromolecular diffusion and release from self-assembled beta-hairpin peptide hydrogels. Biomaterials 2009, 30:1339-1347.
22. Collier J.H., Rudra J.S., Gasiorowski J.Z., Jung J.P. Multi-component extracellular matrices based on peptide self-assembly. Chem Soc Rev 2010, 39:3413-3424.
23. Chung H.J., Park T.G. Self-assembled and nanostructured hydrogels for drug delivery and tissue engineering. Nano Today 2009, 4:429-437.
24. Bhattacharya S., Acharya S.N.G. Pronounced hydrogel formation by the self-assembled aggregates of N-alkyl disaccharide amphiphiles. Chem Mater 1999, 11:3504-3511.
25. Drapeau G.R., Boily Y., Houmard J. Purification and properties of an extracellular protease of Staphylococcus aureus. J Biol Chem 1972, 247:6720-6726.
26. Estroff L.A., Hamilton A.D. Effective gelation of water using a series of bis-urea dicarboxylic acids. Angew Chem Int Ed Engl 2000, 39:3447-3450.
27. Hamachi I., Kiyonaka S., Shinkai S. Solid phase lipid synthesis (SPLS) for construction of an artificial glycolipid library. Chem Commun (Camb) 2000, 1281-1282.
28. Kiyonaka S., Sugiyasu K., Shinkai S., Hamachi I. First thermally responsive supramolecular polymer based on glycosylated amino acid. J Am Chem Soc 2002, 124:10954-10955.
29. Kunitake T. Synthetic bilayer membranes: molecular design, self-organization, and applications. Angew Chem Int Ed Engl 2003, 31:709-726.
30. Barenholz Y. Liposome application: problems and prospects. Curr Opin Colloid Interface Sci 2001, 6:66-77.
31. Panda J.J., Mishra A., Basu A., Chauhan V.S. Stimuli responsive self-assembled hydrogel of a low molecular weight free dipeptide with potential for tunable drug delivery. Biomacromolecules 2008, 9:2244-2250.
32. Vemula P.K., Boilard E., Syed A., Campbell N.R., Muluneh M., Weitz D.A., Lee D.M., Karp J.M. On-demand drug delivery from self-assembled nanofibrous gels: a new approach for treatment of proteolytic disease. J Biomed Mater Res A 2011, 97:103-110.
33. Vemula P.K., Cruikshank G.A., Karp J.M., John G. Self-assembled prodrugs: an enzymatically triggered drug-delivery platform. Biomaterials 2009, 30:383-393.
34. Vemula P.K., Li J., John G. Enzyme catalysis: tool to make and break amygdalin hydrogelators from renewable resources: a delivery model for hydrophobic drugs. J Am Chem Soc 2006, 128:8932-8938.
35. Xing B., Yu C.W., Chow K.H., Ho P.L., Fu D., Xu B. Hydrophobic interaction and hydrogen bonding cooperatively confer a vancomycin hydrogel: a potential candidate for biomaterials. J Am Chem Soc 2002, 124:14846-14847.
36. Gao Y., Kuang Y., Guo Z.F., Guo Z., Krauss I.J., Xu B. Enzyme-instructed molecular self-assembly confers nanofibers and a supramolecular hydrogel of taxol derivative. J Am Chem Soc 2009, 131:13576-13577.
37. Yang Z., Liang G., Ma M., Abbah A.S., Lu W.W., Xu B. d-Glucosamine-based supramolecular hydrogels to improve wound healing. Chem Commun (Camb) 2007, 28:843-845.
38. Bhuniya S., Seo Y.J., Kim B.H. (S)-(+)-Ibuprofen-based hydrogelators: an approach toward anti-inflammatory drug delivery. Tetrahedron Lett 2006, 47:7153-7156.
39. Nicolaou K.C., Guy R.K., Pitsinos E.N., Wrasidlo W. A water-soluble prodrug of taxol with self-assembling properties. Angew Chem Int Ed Engl 1994, 33:1583-1587.
40. Huang X., Brazel C.S. On the importance and mechanisms of burst release in matrix-controlled drug delivery systems. J Control Release 2001, 73:121-136.
41. Syrigos K.N., Rowlinson-Busza G., Epenetos A.A. In vitro cytotoxicity following specific activation of amygdalin by beta-glucosidase conjugated to a bladder cancer-associated monoclonal antibody. Int J Cancer 1998, 78:712-719.
42. Turczan J.W. Nuclear magnetic resonance analysis of pharmaceuticals. Part XV. Determination of sulfamethoxazole and trimethoprim in combination in tablets. Anal Chim Acta 1977, 92:123-128.
43. Wani M.C., Taylor H.L., Wall M.E., Coggon P., McPhail A.T. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 1971, 93:2325-2327.
44. Rowinsky E.K., Onetto N., Canetta R.M., Arbuck S.G. Taxol: the first of the taxanes, an important new class of antitumor agents. Semin Oncol 1992, 19:646-662.
45. Crosasso P., Ceruti M., Brusa P., Arpicco S., Dosio F., Cattel L. Preparation, characterization and properties of sterically stabilized paclitaxel-containing liposomes. J Control Release 2000, 63:19-30.
46. Bae K.H., Lee Y., Park T.G. Oil-encapsulating PEO-PPO-PEO/PEG shell cross-linked nanocapsules for target-specific delivery of paclitaxel. Biomacromolecules 2007, 8:650-656.
47. Tarr B.D., Sambandan T.G., Yalkowsky S.H. A new parenteral emulsion for the administration of taxol. Pharm Res 1987, 4:162-165.
48. Kan P., Chen Z.B., Lee C.J., Chu I.M. Development of nonionic surfactant/phospholipid o/w emulsion as a paclitaxel delivery system. J Control Release 1999, 58:271-278.
49. Nicolaou K.C., Riemer C., Kerr M.A., Rideout D., Wrasidlo W. Design, synthesis and biological activity of protaxols. Nature 1993, 364:464-466.
50. Klevens R.M., Morrison M.A., Nadle J., Petit S., Gershman K., Ray S., et al. Invasive methicillin-resistant Staphylococcus aureus infections in the United States. JAMA 2007, 298:1763-1771.
51. Xing B., Ho P.L., Yu C.W., Chow K.H., Gu H., Xu B. Self-assembled multivalent vancomycin on cell surfaces against vancomycin-resistant enterococci (VRE). Chem Commun (Camb) 2003, 7:2224-2225.
52. Shaunak S., Thomas S., Gianasi E., Godwin A., Jones E., Teo I., et al. Polyvalent dendrimer glucosamine conjugates prevent scar tissue formation. Nat Biotechnol 2004, 22:977-984.