Release behavior and antibiofilm activity of usnic acid-loaded carboxylated poly(l-lactide) microparticles

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 88, Issue 2, 2014, Pages 415-423

  Martinelli, Andrea ^a   Bakry, Ahmed ^b   D'Ilario, Lucio ^a   Francolini, Iolanda ^a   Piozzi, Antonella ^a   Taresco, Vincenzo ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b Helwan University   (Egypt)

Author keywords

Drug delivery; Microbial biofilm; Microparticles; Polylactide; Staphylococcus epidermidis; Usnic acid

Indexed keywords

CARBOXYLATED POLY(L LACTIDE) MICROPARTICLE; POLYMER; SURFACTANT; UNCLASSIFIED DRUG; USNIC ACID; ANTIINFECTIVE AGENT; BENZOFURAN DERIVATIVE; CARBOXYLIC ACID; POLYESTER; POLYLACTIDE;

ANTIMICROBIAL ACTIVITY; ARTICLE; BIOFILM; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG DIFFUSION; DRUG RELEASE; DRUG SOLUBILITY; MICROSCOPY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR WEIGHT; POLYMERIZATION; SCANNING ELECTRON MICROSCOPY; STAPHYLOCOCCUS EPIDERMIDIS; TEMPERATURE DEPENDENCE; THERMOGRAPHY; CHEMISTRY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG EFFECTS;

ANTI-BACTERIAL AGENTS; BENZOFURANS; BIOFILMS; CALORIMETRY, DIFFERENTIAL SCANNING; CARBOXYLIC ACIDS; MICROSCOPY, ELECTRON, SCANNING; POLYESTERS; STAPHYLOCOCCUS EPIDERMIDIS;

EID: 84908365388     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2014.06.002     Document Type: Article

References (50)

1. N. Hoiby, O. Ciofu, H.K. Johansen, Z.J. Song, C. Moser, P.O. Jensen, S. Molin, M. Givskov, T. Tolker-Nielsen, and T. Bjarnsholt The clinical impact of bacterial biofilms Int. J. Oral. Sci. 3 2011 55 65
2. J.W. Costerton, P.S. Stewart, and E.P. Greenberg Bacterial biofilms: a common cause of persistent infections Science 284 1999 1318 1322
3. T. Bjarnsholt, O. Ciofu, S. Molin, M. Givskov, and N. Hoiby Applying insights from biofilm biology to drug development - can a new approach be developed? Nat. Rev. Drug Discov. 12 2013 791 808
4. D. Campoccia, L. Montanaro, and C.R. Arciola A review of the biomaterials technologies for infection-resistant surfaces Biomaterials 34 2013 8533 8554
5. I. Francolini, F. Crisante, A. Martinelli, L. D'Ilario, and A. Piozzi Synthesis of biomimetic segmented polyurethanes as antifouling biomaterials Acta Biomater. 8 2012 549 558
6. W.S. Cheow, M.W. Chang, and K. Hadinoto Antibacterial efficacy of inhalable antibiotic-encapsulated biodegradable polymeric nanoparticles against E. coli biofilm cells J. Biomed. Nanotechnol. 6 2010 391 403
7. S.K. Lai, Y.Y. Wang, and J. Hanes Mucus-penetrating nanoparticles for drug and gene delivery to mucosal tissues Adv. Drug Deliv. Rev. 61 2009 158 171
8. P. Meers, M. Neville, V. Malinin, A.W. Scotto, G. Sardaryan, R. Kurumunda, C. Mackinson, G. James, S. Fisher, and W.R. Perkins Biofilm penetration, triggered release and in vivo activity of inhaled liposomal amikacin in chronic Pseudomonas aeruginosa lung infections J. Antimicrob. Chemother. 61 2008 859 868
9. M. Cocchietto, N. Skert, P. Nimis, and G. Sava A review on usnic acid: an interesting natural compound Naturwissenschaften 89 2002 137 146
10. A. Pompilio, S. Pomponio, V. Di Vincenzo, V. Crocetta, M. Nicoletti, M. Piovano, J.A. Garbarino, and G. Di Bonaventura Antimicrobial and antibiofilm activity of secondary metabolites of lichens against methicillin-resistant Staphylococcus aureus strains from cystic fibrosis patients Future Microbiol. 8 2013 281 292
11. I. Francolini, V. Taresco, F. Crisante, A. Martinelli, L. D'Ilario, and A. Piozzi Water soluble usnic acid-polyacrylamide complexes with enhanced antimicrobial activity against Staphylococcus epidermidis Int. J. Mol. Sci. 14 2013 7356 7369
12. M. Lauterwein, M. Oethinger, K. Belsner, T. Peters, and R. Marre In vitro activities of the lichen secondary metabolites vulpinic acid, (+)-usnic acid, and (-)-usnic acid against aerobic and anaerobic microorganisms Antimicrob. Agents Chemother. 39 1995 2541 2543
13. R.H. Pires, R. Lucarini, and M.J. Mendes-Giannini Effect of usnic acid on Candida orthopsilosis and C. parapsilosis Antimicrob. Agents Chemother. 56 2012 595 597
14. D.F. Ramos, and P.E. Almeida da Silva Antimycobacterial activity of usnic acid against resistant and susceptible strains of Mycobacterium tuberculosis and non-tuberculous mycobacteria Pharm. Biol. 48 2010 260 263
15. S. Kim, R. Greenleaf, M.C. Miller, L. Satish, S. Kathju, G. Ehrlich, J.C. Post, N.G. Sotereanos, and P. Stoodley Mechanical effects, antimicrobial efficacy and cytotoxicity of usnic acid as a biofilm prophylaxis in PMMA J. Mater. Sci. - Mater. Med. 22 2011 2773 2780
16. I. Francolini, P. Norris, A. Piozzi, G. Donelli, and P. Stoodley Usnic acid, a natural antimicrobial agent able to inhibit bacterial biofilm formation on polymer surfaces Antimicrob. Agents Chemother. 48 2004 4360 4365
17. M. Otto Staphylococcus epidermidis - the 'accidental' pathogen Nat. Rev. Microbiol. 7 2009 555 567
18. V.K. Gupta, S. Verma, S. Gupta, A. Singh, A. Pal, S.K. Srivastava, P.K. Srivastava, S.C. Singh, and M.P. Darokar Membrane-damaging potential of natural l-(-)-usnic acid in Staphylococcus aureus Eur. J. Clin. Microbiol. Infect. Dis. 31 2012 3375 3383
19. M.C. Lira, M.P. Siqueira-Moura, H.M. Rolim-Santos, F.C. Galetti, A.R. Simioni, N.P. Santos, E.S. Tabosa Do Egito, C.L. Silva, A.C. Tedesco, and N.S. Santos-Magalhaes In vitro uptake and antimycobacterial activity of liposomal usnic acid formulation J. Liposome Res. 19 2009 49 58
20. N.P. da Silva Santos, S.C. Nascimento, M.S. Wanderley, N.T. Pontes-Filho, J.F. da Silva, C.M. de Castro, E.C. Pereira, N.H. da Silva, N.K. Honda, and N.S. Santos-Magalhaes Nanoencapsulation of usnic acid: an attempt to improve antitumour activity and reduce hepatotoxicity Eur. J. Pharm. Biopharm. 64 2006 154 160
21. G.A.R. Nobes, D. Maysinger, and R.H. Marchessault Polyhydroxyalkanoates: materials for delivery systems Drug Deliv. 5 1998 167 177
22. L. Nobs, F. Buchegger, R. Gurny, and E. Allemann Surface modification of poly(lactic acid) nanoparticles by covalent attachment of thiol groups by means of three methods Int. J. Pharm. 250 2003 327 337
23. L. D'Ilario, I. Francolini, A. Martinelli, and A. Piozzi Dipyridamole-loaded poly(l-lactide) single crystals as drug delivery systems Macromol. Rapid Comm. 28 2007 1900 1904
24. G. Casini, L. Petrone, A. Bakry, I. Francolini, P. Di Bonito, C. Giorgi, A. Martinelli, A. Piozzi, and L. D'Ilario Functionalized poly(l-lactide) single crystals coated with antigens in development of vaccines J. Control. Release 148 2010 e106 e108
25. K.S. Soppimath, T.M. Aminabhavi, A.R. Kulkarni, and W.E. Rudzinski Biodegradable polymeric nanoparticles as drug delivery devices J. Control. Release 70 2001 1 20
26. R.T. Liggins, and H.M. Burt Paclitaxel loaded poly(l-lactic acid) (PLLA) microspheres. II. The effect of processing parameters on microsphere morphology and drug release kinetics Int. J. Pharm. 281 2004 103 106
27. S. Izumikawa, S. Yoshioka, Y. Aso, and Y. Takeda Preparation of poly(l-lactide) microspheres of different crystalline morphology and effect of crystalline morphology on drug release rate J. Control. Release 15 1991 133 140
28. N. Kayaman-Apohan, and Z.S. Akdemir Synthesis and characterization of pendant carboxylic acid functional poly(lactic acid) and poly(lactic-co-glycolic acid) and their drug release behaviors Polym. Adv. Technol. 16 2005 807 812
29. S. Hyvonen, L. Peltonen, M. Karjalainen, and J. Hirvonen Effect of nanoprecipitation on the physicochemical properties of low molecular weight poly(l-lactic acid) nanoparticles loaded with salbutamol sulphate and beclomethasone dipropionate Int. J. Pharm. 295 2005 269 281
30. S.K. Sahoo, J. Panyam, S. Prabha, and V. Labhasetwar Residual polyvinyl alcohol associated with poly(d,l-lactide-co-glycolide) nanoparticles affects their physical properties and cellular uptake J. Control. Release 82 2002 105 114
31. A.J. Ten Tije, J. Verweij, W.J. Loos, and A. Sparreboom Pharmacological effects of formulation vehicles: implications for cancer chemotherapy Clin. Pharmacokinet. 42 2003 665 685
32. T. Ouchi, M. Toyohara, H. Arimura, and Y. Ohya Preparation of poly(l-lactide)-based microspheres having a cationic or anionic surface using biodegradable surfactants Biomacromolecules 3 2002 885 888
33. A. Carrio, G. Schwach, J. Coudane, and M. Vert Preparation and degradation of surfactant-free PLAGA microspheres J. Control. Release 37 1995 133-121
34. Z. Zhang, and S.-S. Feng Nanoparticles of poly(lactide)/vitamin E TPGS copolymer for cancer chemotherapy: synthesis, formulation, characterization and in vitro drug release Biomaterials 27 2006 262 270
35. S.L. Percival, K.E. Hill, D.W. Williams, S.J. Hooper, D.W. Thomas, and J.W. Costerton A review of the scientific evidence for biofilms in wounds Wound Repair Regen. 20 2012 647 657
36. M.F. Valle, N.M. Maruthur, L.M. Wilson, M. Malas, U. Qazi, E. Haberl, E.B. Bass, J. Zenilman, and G. Lazarus Comparative effectiveness of advanced wound dressings for patients with chronic venous leg ulcers: a systematic review Wound Repair Regen. 22 2014 193 204
37. J.G. Thomas, W. Slone, S. Linton, L. Corum, and S.L. Percival A comparison of the antimicrobial efficacy of two silver-containing wound dressings on burn wound isolates J. Wound Care 20 2011 580 586
38. J.E. Lee, J.C. Park, K.H. Lee, S.H. Oh, J.G. Kim, and H. Suh An infection-preventing bilayered collagen membrane containing antibiotic-loaded hyaluronan microparticles: physical and biological properties Artif. Organs 26 7 2002 636 646
39. B. Albertini, M. Di Sabatino, N. Calonghi, L. Rodriguez, and N. Passerini Novel multifunctional platforms for potential treatment of cutaneous wounds: development and in vitro characterization Int. J. Pharm. 440 2 2013 238 249
40. J. Jin, Y. Rao, X. Bian, A. Zeng, and G. Yang Solubility of (+)-usnic acid in water, ethanol, acetone, ethyl acetate and n-hexane J. Solution Chem. 42 2013 1018 1027
41. T.G. Fox, and P.J. Flory Second order transition temperatures and related properties of polystyrene. I. Influence of molecular weight J. Appl. Phys. 21 1950 581 585
42. K. Jamshidi, S. Hyon, and Y. Ikada Thermal characterization of polylactides Polymer 29 1988 2229 2234
43. J.C. Jeong, J. Lee, and K. Cho Effects of crystalline microstructure on drug release behavior of poly(epsilon-caprolactone) microspheres J. Control. Release 92 2003 249 258
44. D. Han, K. Matsumaru, D. Rettori, and N. Kaplowitz Usnic acid-induced necrosis of cultured mouse hepatocytes: inhibition of mitochondrial function and oxidative stress Biochem. Pharmacol. 67 2004 439 451
45. M. Takai, Y. Uehara, and J.A. Beisler Usnic acid derivatives as potential antineoplastic agents J. Med. Chem. 22 1979 1380 1384
46. K. Jamshidi, S.H. Hyon, and Y. Ikada Thermal characterization of polylactides Polymer 29 1988 2229 2234
47. M. Fierheller, and R.G. Sibbald A clinical investigation into the relationship between increased periwound skin temperature and local wound infection in patients with chronic leg ulcers Adv. Skin Wound Care 23 8 2010 369 379
48. D. Ma, and A.J. McHugh The interplay of membrane formation and drug release in solution-cast films of polylactide polymers Int. J. Pharm. 388 2010 1 12
49. L.R. Hilden, and K.R. Morris Physics of amorphous solids J. Pharm. Sci. 93 2004 3 12
50. W. Zhu, T. Masaki, Y.H. Bae, R. Rathi, A.K. Cheung, and S.E. Kern Development of a sustained-release system for perivascular delivery of dipyridamole J. Biomed. Mater. Res. B Appl. Biomater. 77 2006 135 143