Antibiotic-containing polymers for localized, sustained drug delivery

Advanced Drug Delivery Reviews

Volumn 78, Issue , 2014, Pages 77-87

  Stebbins, Nicholas D ^a   Ouimet, Michelle A ^a   Uhrich, Kathryn E ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

Biocompatible; Controlled release; Localized delivery antibiotics; Polymer conjugates; Sustained release

Indexed keywords

ANTIBIOTICS; BIOCOMPATIBILITY; POLYMERS; TARGETED DRUG DELIVERY;

BIOCOMPATIBLE; CONTROLLED RELEASE; LOCALIZED DELIVERY; POLYMER CONJUGATE; SUSTAINED RELEASE;

CONTROLLED DRUG DELIVERY;

ACRIFLAVINE; AMINOGLYCOSIDE ANTIBIOTIC AGENT; ANTIBIOTIC AGENT; BETA LACTAM ANTIBIOTIC; CEFRADINE; CIPROFLOXACIN; DIMETICONE; FERULIC ACID; GENTAMICIN; LEVOFLOXACIN; MACROGOL; NORFLOXACIN; OFLOXACIN; PENICILLIN DERIVATIVE; PENICILLIN G; PENICILLIN V; POLITEF; POLYAMIDOAMINE; POLYMER; QUINOLINE DERIVED ANTIINFECTIVE AGENT; SULFAMETHOXAZOLE; SULFONAMIDE; ANTIINFECTIVE AGENT; DELAYED RELEASE FORMULATION;

ANTIBACTERIAL ACTIVITY; ATOMIC FORCE MICROSCOPY; BIOCOMPATIBILITY; BROTH DILUTION; CENTRIFUGATION; CHEMICAL COMPOSITION; CONTROLLED RELEASE FORMULATION; COVALENT BOND; DRUG CONJUGATION; DRUG DEGRADATION; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG STRUCTURE; ENCAPSULATION; GEL PERMEATION CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENOLYSIS; INFRARED SPECTROSCOPY; LIGHT SCATTERING; MOLECULAR WEIGHT; PARTICLE SIZE; POLYMERIZATION; REVIEW; SCANNING ELECTRON MICROSCOPY; STOICHIOMETRY; SUSTAINED DRUG RELEASE; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY; ZETA POTENTIAL; ANIMAL; ANTIBIOTIC RESISTANCE; BACTERIAL INFECTIONS; CHEMISTRY; DELAYED RELEASE FORMULATION; DRUG DESIGN; DRUG RELEASE; HALF LIFE TIME; HUMAN; MICROBIOLOGY;

ANIMALS; ANTI-BACTERIAL AGENTS; BACTERIAL INFECTIONS; DELAYED-ACTION PREPARATIONS; DRUG DELIVERY SYSTEMS; DRUG DESIGN; DRUG LIBERATION; DRUG RESISTANCE, BACTERIAL; HALF-LIFE; HUMANS; POLYMERS;

EID: 84919698126     PISSN: 0169409X     EISSN: 18728294     Source Type: Journal    
DOI: 10.1016/j.addr.2014.04.006     Document Type: Review

References (55)

1. Wright G.D. Bacterial resistance to antibiotics: enzymatic degradation and modification. Adv. Drug Deliv. Rev. 2005, 57:1451-1470.
2. Hetrick E.M., Schoenfisch M.H. Reducing implant-related infections: active release strategies. Chem. Soc. Rev. 2006, 35:780.
3. Smith A.W. Biofilms and antibiotic therapy: is there a role for combating bacterial resistance by the use of novel drug delivery systems?. Adv. Drug Deliv. Rev. 2005, 57:1539-1550.
4. Chambers H.F., DeLeo F.R. Waves of resistance: Staphylococcus aureus in the antibiotic era. Nat. Rev. Microbiol. 2009, 7:629-641.
5. Fisher J.F., Meroueh S.O., Mobashery S. Bacterial resistance to β-lactam antibiotics: compelling opportunism, compelling opportunity. Chem. Rev. (Washington, DC, U. S.) 2005, 105:395-424.
6. Levy S.B., Marshall B. Antibacterial resistance worldwide: causes, challenges and responses. Nat. Med. 2004, 10:S122-S129.
7. French G.L. Clinical impact and relevance of antibiotic resistance. Adv. Drug Deliv. Rev. 2005, 57:1514-1527.
8. Livermore D. Can better prescribing turn the tide of resistance?. Nat. Rev. Microbiol. 2004, 2:73-78.
9. Wu P., Grainger D.W. Drug/device combinations for local drug therapies and infection prophylaxis. Biomaterials 2006, 27:2450-2467.
10. Kost J., Langer R. Responsive polymeric delivery systems. Advanced Drug Delivery Reviews 2012, 64:327-341. (Supplement).
11. Uhrich K.E., Cannizzaro S.M., Langer R.S., Shakesheff K.M. Polymeric systems for controlled drug release. Chem. Rev. (Washington, D. C.) 1999, 99:3181-3198.
12. Khandare J., Minko T. Polymer-drug conjugates: progress in polymeric prodrugs. Prog. Polym. Sci. 2006, 31:359-397.
13. Qiu L.Y., Bae Y.H. Polymer architecture and drug delivery. Pharm. Res. 2006, 23:1-30.
14. Hoare T.R., Kohane D.S. Hydrogels in drug delivery: progress and challenges. Polymer 2008, 49:1993-2007.
15. Siepmann F., Siepmann J., Walther M., MacRae R.J., Bodmeier R. Polymer blends for controlled release coatings. J. Control. Release 2008, 125:1-15.
16. Edlund U., Albertsson A.C. Degradable polymer microspheres for controlled drug delivery. Degradable Aliphatic Polyesters 2002, 67-112. Springer Berlin Heidelberg.
17. Göpferich A., Tessmar J. Polyanhydride degradation and erosion. Adv. Drug Deliv. Rev. 2002, 54:911-931.
18. Prudencio A., Schmeltzer R.C., Uhrich K.E. Effect of linker structure on salicylic acid-derived poly(anhydride-esters). Macromolecules 2005, 38:6895-6901.
19. Liu S., Maheshwari R., Kiick K.L. Polymer-based therapeutics. Macromolecules (Washington, DC, U. S.) 2009, 42:3-13.
20. Demain A.L. Antibiotics: natural products essential to human health. Med. Res. Rev. 2009, 29:821-842.
21. Nathan A., Zalipsky S., Ertel S.I., Agathos S.N., Yarmush M.L., Kohn J. Copolymers of lysine and polyethylene glycol: a new family of functionalized drug carriers. Bioconjug. Chem. 1993, 4:54-62.
22. Yang H., Lopina S.T. Penicillin V-conjugated PEG-PAMAM star polymers. J. Biomater. Sci. Polym. Ed. 2003, 14:1043-1056.
23. Aumsuwan N., Heinhorst S., Urban M.W. The effectiveness of antibiotic activity of penicillin attached to expanded poly(tetrafluoroethylene) (ePTFE) surfaces: a quantitative assessment. Biomacromolecules 2007, 8:3525-3530.
24. Aumsuwan N., Heinhorst S., Urban M.W. Antibacterial surfaces on expanded polytetrafluoroethylene; penicillin attachment. Biomacromolecules 2007, 8:713-718.
25. Ustariz-Peyret C., Coudane J., Vert M., Kaltsatos V., Boisramene B. Labile conjugation of a hydrophilic drug to PLA oligomers to modify a drug delivery system: cephradin in a PLAGA matrix. J. Microencapsul. 2000, 17:615-624.
26. Adhami Z.N., Wise R., Weston D., Crump B. The pharmacokinetics and tissue penetration of norfloxacin. J. Antimicrob. Chemother. 1984, 13:87-92.
27. Coessens V., Schacht E.H., Domurado D. Synthesis and in vitro stability of macromolecular prodrugs of norfloxacin. J. Control. Release 1997, 47:283-291.
28. Roseeuw E., Coessens V., Schacht E., Vrooman B., Domurado D., Marchal G. Polymeric prodrugs of antibiotics with improved efficiency. J. Mater. Sci. Mater. Med. 1999, 10:743-746.
29. Gac-Breton S., Coudane J., Boustta M., Vert M. Norfloxacin-poly(l-lysine citramide imide) conjugates and structure-dependence of the drug release. J. Drug Target. 2004, 12:297-307.
30. Sobczak M., Witkowska E., Oledzka E., Kolodziejski W. Synthesis and structural analysis of polyester prodrugs of norfloxacin. Molecules 2008, 13:96-106.
31. Sobczak M. Synthesis and characterization of polyester conjugates of ciprofloxacin. Eur. J. Med. Chem. 2010, 45:3844-3849.
32. Sobczak M., Nalecz-Jawecki G., Kolodziejski W.L., Gos P., Zoltowska K. Synthesis and study of controlled release of ofloxacin from polyester conjugates. Int. J. Pharm. 2010, 402:37-43.
33. Sobczak M., Nurzynska K., Kolodziejski W. Seeking polymeric prodrugs of norfloxacin. Part 2. Synthesis and structural analysis of polyurethane conjugates. Molecules 2010, 15:842-856.
34. Yang M., Santerre J.P. Utilization of quinolone drugs as monomers: characterization of the synthesis reaction products for poly(norfloxacin diisocyanatododecane polycaprolactone). Biomacromolecules 2001, 2:134-141.
35. Woo G.L.Y., Yang M.L., Yin H.Q., Jaffer F., Mittelman M.W., Santerre J.P. Biological characterization of a novel biodegradable antimicrobial polymer synthesized with fluoroquinolones. J. Biomed. Mater. Res. 2002, 59:35-45.
36. Woo G.L.Y., Mittelman M.W., Santerre J.P. Synthesis and characterization of a novel biodegradable antimicrobial polymer. Biomaterials 2000, 21:1235-1246.
37. Kugel A., Chisholm B., Ebert S., Jepperson M., Jarabek L., Stafslien S. Antimicrobial polysiloxane polymers and coatings containing pendant levofloxacin. Polym. Chem. 2010, 1:442-452.
38. Coessens V., Schacht E., Domurado D. Synthesis of polyglutamine and dextran conjugates of streptomycin with an acid-sensitive drug-carrier linkage. J. Control. Release 1996, 38:141-150.
39. Patel H., Raval D.A., Madamwar D., Sinha T.J.M. Polymeric prodrugs. Synthesis, release study, and antimicrobial properties of polymer-bound acriflavine. Angew. Makromol. Chem. 1997, 245:1-8.
40. Patel H., Raval A.D., Madamawar D., Patel S.R. Polymeric prodrug. Synthesis, release study, and antimicrobial property of poly(styrene-co-maleic anhydride)-bound acriflavine. Angew. Makromol. Chem. 1998, 263:25-30.
41. Kumar N., Langer R.S., Domb A.J. Polyanhydrides: an overview. Adv. Drug Deliv. Rev. 2002, 54:889-910.
42. Turos E., Shim J.-Y., Wang Y., Greenhalgh K., Reddy G.S.K., Dickey S., Lim D.V. Antibiotic-conjugated polyacrylate nanoparticles: new opportunities for development of anti-methicillin-resistant Staphylococcus aureus agents. Bioorg. Med. Chem. Lett. 2007, 17:53-56.
43. Turos E., Reddy G.S.K., Greenhalgh K., Ramaraju P., Abeylath S.C., Jang S., Dickey S., Lim D.V. Penicillin-bound polyacrylate nanoparticles: restoring the activity of beta-lactam antibiotics against MRSA. Bioorg. Med. Chem. Lett. 2007, 17:3468-3472.
44. Greenhalgh K., Turos E. In vivo studies of polyacrylate nanoparticle emulsions for topical and systemic applications. Nanomedicine (N. Y., NY, U. S.) 2009, 5:46-54.
45. Uhrich K.E., Prudencio A. Ampicillin and amoxicillin-based poly(anhydride-amides) for medical devices. Rutgers 2009, The State University of New Jersey, USA, (pp. 37pp.).
46. Moon W.-S., Kim J.C., Chung K.-H., Park E.-S., Kim M.-N., Yoon J.-S. Antimicrobial activity of a monomer and its polymer based on quinolone. J. Appl. Polym. Sci. 2003, 90:1797-1801.
47. Dizman B., Elasri M.O., Mathias L.J. Synthesis, characterization, and antibacterial activities of novel methacrylate polymers containing norfloxacin. Biomacromolecules 2005, 6:514-520.
48. Chen M., Hu M., Wang D., Wang G., Zhu X., Yan D., Sun J. Multifunctional hyperbranched glycoconjugated polymers based on natural aminoglycosides. Bioconjug. Chem. 2012, 23:1189-1199.
49. Chang H.-P., Chen J.-Y., Zhong P.-S., Chang Y.-H., Liang M. Synthesis and characterization of a new polymer-drug conjugate with pH-induced activity. Polymer 2012, 53:3498-3507.
50. Schmeltzer R.C., Anastasiou T.J., Uhrich K.E. Optimized synthesis of salicylate-based poly (anhydride-esters). Polym. Bull. (Berlin, Ger.) 2003, 49:441-448.
51. Erdmann L., Uhrich K.E. Synthesis and degradation characteristics of salicylic acid-derived poly(anhydride-esters). Biomaterials 2000, 21:1941-1946.
52. Bryers J.D., Jarvis R.A., Lebo J., Prudencio A., Kyriakides T.R., Uhrich K. Biodegradation of poly(anhydride-esters) into non-steroidal anti-inflammatory drugs and their effect on Pseudomonas aeruginosa biofilms in vitro and on the foreign-body response in vivo. Biomaterials 2006, 27:5039-5048.
53. Rosenberg L.E., Carbone A.L., Roemling U., Uhrich K.E., Chikindas M.L. Salicylic acid-based poly(anhydride esters) for control of biofilm formation in Salmonella enterica serovar Typhimurium. Lett. Appl. Microbiol. 2008, 46:593-599.
54. Puupponen-Pimia R., Nohynek L., Meier C., Kahkonen M., Heinonen M., Hopia A., Oksman-Caldentey K.M. Antimicrobial properties of phenolic compounds from berries. J. Appl. Microbiol. 2001, 90:494-507.
55. Ouimet M.A., Griffin J., Carbone-Howell A.L., Wu W.-H., Stebbins N.D., Di R., Uhrich K.E. Biodegradable ferulic acid-containing poly(anhydride-ester): degradation products with controlled release and sustained antioxidant activity. Biomacromolecules 2013, 14:854-861.