title: Synthesis of ciprofloxacin-conjugated poly (L-lactic acid) polymer for nanofiber fabrication and antibacterial evaluation.
abstract: Ciprofloxacin was conjugated with polylactide (PLA) via the secondary amine group of the piperazine ring using PLA and 7-(4-(2-Chloroacetyl) piperazin-1-yl)-1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid. Zinc prolinate, a biocompatible catalyst was synthesized, characterized, and used in ring opening polymerization of L-lactide. Five different kinds of OH-terminated poly(L-lactide) (two-, three-, four-, six-arm, star-shaped) homopolymers were synthesized by ring opening polymerization of L-lactide in the presence of dodecanol, glycerol, pentaerythritol, dipentaerythritol as initiator and zinc prolinate as a catalyst. The structures of the polymers and conjugates were thoroughly characterized by means of gel permeation chromatography, matrix-assisted laser desorption/ionization - time of flight mass spectrometry, and nuclear magnetic resonance spectroscopy. PLA (molecular weight =100,000) and ciprofloxacin conjugated PLA were used for fabrication of nonwoven nanofiber mat (diameter ranges; 150-400 nm) having pore size (62-102 nm) using electrospinning. The microbiological assessment shows that the release of ciprofloxacin possesses antimicrobial activity. The drug-release behavior of the mat was studied to reveal potential application as a drug delivery system. The result shows that the ciprofloxacin release rates of the PLA conjugate nonwoven nanofiber mat could be controlled by the drug loading content and the release medium. The development of a biodegradable ciprofloxacin system, based on nonwoven nanofiber mat, should be of great interest in drug delivery systems.
authors.affiliation: Polymer Science and Engineering Division, National Chemical Laboratory, Pune, India.
authors.forename: Sharad P
authors.initials: SP
authors.lastname: Parwe
authors.affiliation: Polymer Science and Engineering Division, National Chemical Laboratory, Pune, India.
authors.forename: Priti N
authors.initials: PN
authors.lastname: Chaudhari
authors.affiliation: Polymer Science and Engineering Division, National Chemical Laboratory, Pune, India.
authors.forename: Kavita K
authors.initials: KK
authors.lastname: Mohite
authors.affiliation: Polymer Science and Engineering Division, National Chemical Laboratory, Pune, India.
authors.forename: Balaji S
authors.initials: BS
authors.lastname: Selukar
authors.affiliation: Polymer Science and Engineering Division, National Chemical Laboratory, Pune, India.
authors.forename: Smita S
authors.initials: SS
authors.lastname: Nande
authors.affiliation: Polymer Science and Engineering Division, National Chemical Laboratory, Pune, India.
authors.forename: Baijayantimala
authors.initials: B
authors.lastname: Garnaik
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D002939:Ciprofloxacin / Q000008:administration & dosage* / Q000737:chemistry; D019344:Lactic Acid / Q000737:chemistry*; D053769:Nanocapsules / Q000008:administration & dosage / Q000737:chemistry* / Q000648:ultrastructure; D057139:Nanofibers / Q000008:administration & dosage / Q000737:chemistry* / Q000648:ultrastructure; D010316:Particle Size; D011091:Polyesters; D011108:Polymers / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects* / Q000502:physiology
chemical_list: D000900:Anti-Bacterial Agents; D053769:Nanocapsules; D011091:Polyesters; D011108:Polymers; D019344:Lactic Acid; C033616:poly(lactide); D002939:Ciprofloxacin
keywords: CP-PLA; MDR; antibacterial activity; ciprofloxacin conjugated polylactides; drug release; electrospinning; nonwoven nanofibers; zinc prolinate
references.citation: Microbiol Mol Biol Rev. 1997 Sep;61(3):377-92
references.pmid: 9293187
references.citation: Biochemistry. 1989 May 2;28(9):3886-94
references.pmid: 2546585
references.citation: Appl Environ Microbiol. 2000 Jun;66(6):2664-7
references.pmid: 10831454
references.citation: Molecules. 2009 Feb 04;14(2):621-32
references.pmid: 19214152
references.citation: Biomaterials. 2000 Jun;21(12):1235-46
references.pmid: 10811305
references.citation: Chem Rev. 2001 Dec;101(12):3793-818
references.pmid: 11740921
references.citation: Biomaterials. 2004 Feb;25(5):877-86
references.pmid: 14609676
references.citation: J Mater Sci Mater Med. 2005 Feb;16(2):95-100
references.pmid: 15744596
references.citation: Adv Drug Deliv Rev. 2003 Apr 25;55(4):501-18
references.pmid: 12706048
references.citation: Biomacromolecules. 2003 May-Jun;4(3):828-34
references.pmid: 12741805
references.citation: Chem Rev. 1999 Nov 10;99(11):3181-98
references.pmid: 11749514
references.citation: Carbohydr Polym. 2012 Nov 6;90(4):1786-93
references.pmid: 22944448
references.citation: J Am Chem Soc. 2003 Sep 17;125(37):11350-9
references.pmid: 16220958
references.citation: Appl Microbiol Biotechnol. 2001 Aug;56(3-4):474-7
references.pmid: 11549022
references.citation: Appl Biochem Biotechnol. 2005 Jun;125(3):147-58
references.pmid: 15917579
references.citation: Bioorg Med Chem Lett. 2009 Mar 1;19(5):1496-8
references.pmid: 19179071
references.citation: Chem Commun (Camb). 2003 May 7;(9):1090-1
references.pmid: 12772917
references.citation: J Mater Sci Mater Med. 2006 Dec;17(12):1275-82
references.pmid: 17143759
references.citation: Surg Neurol. 2006 Jan;65(1):38-41; discussion 41
references.pmid: 16378851
references.citation: Acta Orthop. 2008 Apr;79(2):295-301
references.pmid: 18484258
references.citation: J Microencapsul. 1997 Mar-Apr;14(2):155-61
references.pmid: 9132467
references.citation: Biomacromolecules. 2003 Nov-Dec;4(6):1466-86
references.pmid: 14606869
references.citation: Eur J Med Chem. 2010 Sep;45(9):3844-9
references.pmid: 20541292