{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,21]],"date-time":"2026-02-21T09:50:28Z","timestamp":1771667428022,"version":"3.50.1"},"reference-count":32,"publisher":"Hindawi Limited","license":[{"start":{"date-parts":[[2013,5,2]],"date-time":"2013-05-02T00:00:00Z","timestamp":1367452800000},"content-version":"unspecified","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"funder":[{"name":"University of Nebraska at Omaha"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Journal of Pharmaceutics"],"published-print":{"date-parts":[[2013,5,2]]},"abstract":"<jats:p><jats:italic>Escherichia coli<\/jats:italic> (<jats:italic>E. coli<\/jats:italic>) is associated with necrotizing fasciitis (type I) and can induce enough damage to tissue  causing hypoxia.  Three ester derivatives of the broad-spectrum antibiotic ciprofloxacin were placed into bacteria culture simultaneously with the parent ciprofloxacin (drug 1) to ascertain the level of antibacterial activity.  The n-propyl (drug 2),  n-pentyl (drug 3), and n-octyl (drug 4) esters of ciprofloxacin were synthesized under mixed phase conditions and by microwave excitation.  The formation of ester derivatives of ciprofloxacin modified important molecular properties such as Log <jats:italic>P<\/jats:italic> and polar surface area which improves tissue penetration, yet preserved strong antibacterial activity. The Log <jats:italic>P<\/jats:italic> values for drugs 1, 2, 3, and 4 became \u22120.701, 0.437, 1.50, and 3.02, respectively.  The polar surface areas for drugs 1, 2, 3, and 4 were determined to be 74.6 Angstroms<jats:sup>2<\/jats:sup>, 63.6 Angstroms<jats:sup>2<\/jats:sup>, 63.6 Angstroms<jats:sup>2<\/jats:sup>, and 63.6 Angstroms<jats:sup>2<\/jats:sup>, respectively. These values of Log <jats:italic>P<\/jats:italic> and polar surface area improved tissue penetration, as indicated by the determination of dermal permeability coefficient (<mml:math xmlns:mml=\"http:\/\/www.w3.org\/1998\/Math\/MathML\" id=\"M1\"><mml:mrow><mml:msub><mml:mrow><mml:mi>K<\/mml:mi><\/mml:mrow><mml:mrow><mml:mi>p<\/mml:mi><\/mml:mrow><\/mml:msub><\/mml:mrow><\/mml:math>) and subsequently into the superficial fascial layer. All drugs induced greater than 60% bacterial cell death at concentrations less than 1.0 micrograms\/milliliter. The ester derivatives of ciprofloxacin showed strong antibacterial activity toward penicillin resistant <jats:italic>E. coli<\/jats:italic>.<\/jats:p>","DOI":"10.1155\/2013\/517638","type":"journal-article","created":{"date-parts":[[2013,5,3]],"date-time":"2013-05-03T05:48:09Z","timestamp":1367560089000},"page":"1-7","source":"Crossref","is-referenced-by-count":5,"title":["Antibacterial Derivatives of Ciprofloxacin to Inhibit Growth of Necrotizing Fasciitis Associated Penicillin Resistant <i>Escherichia coli<\/i>"],"prefix":"10.1155","volume":"2013","author":[{"given":"Ronald","family":"Bartzatt","sequence":"first","affiliation":[{"name":"University of Nebraska, College of Arts & Sciences, Durham Science Center, Department of Chemistry, Omaha, NE 68182, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Suat L. G.","family":"Cirillo","sequence":"additional","affiliation":[{"name":"Texas A & M Health Science Center, Department of Microbial and Molecular Pathogenesis, Bryan, TX 77807, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jeffrey D.","family":"Cirillo","sequence":"additional","affiliation":[{"name":"Texas A & M Health Science Center, Department of Microbial and Molecular Pathogenesis, Bryan, TX 77807, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"98","reference":[{"issue":"3","key":"1","doi-asserted-by":"crossref","first-page":"151","DOI":"10.5435\/00124635-200005000-00002","volume":"8","year":"2000","journal-title":"The Journal of the American Academy of Orthopaedic Surgeons"},{"key":"2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jamcollsurg.2008.10.032"},{"key":"3","doi-asserted-by":"publisher","DOI":"10.1136\/pgmj.75.889.645"},{"key":"4","doi-asserted-by":"publisher","DOI":"10.1128\/JCM.00491-10"},{"key":"5","doi-asserted-by":"publisher","DOI":"10.1016\/S1473-3099(06)70526-6"},{"key":"6","doi-asserted-by":"publisher","DOI":"10.1016\/S1015-9584(10)60009-7"},{"issue":"12","key":"7","first-page":"711","volume":"13","year":"2003","journal-title":"Journal of the College of Physicians and Surgeons Pakistan"},{"issue":"6","key":"8","doi-asserted-by":"crossref","first-page":"604","DOI":"10.1016\/0090-4295(79)90379-0","volume":"13","year":"1979","journal-title":"Urology"},{"key":"9","doi-asserted-by":"publisher","DOI":"10.1002\/qsar.19960150604"},{"key":"10","doi-asserted-by":"publisher","DOI":"10.1021\/js9804011"},{"key":"11","doi-asserted-by":"publisher","DOI":"10.1021\/jm000942e"},{"issue":"11","key":"12","doi-asserted-by":"crossref","first-page":"1065","DOI":"10.1097\/00007611-199711000-00001","volume":"90","year":"1997","journal-title":"Southern Medical Journal"},{"issue":"2","key":"13","doi-asserted-by":"crossref","first-page":"145","DOI":"10.2165\/00002512-199404020-00007","volume":"4","year":"1994","journal-title":"Drugs and Aging"},{"issue":"178","key":"14","first-page":"139","volume":"49","year":"2010","journal-title":"Journal of the Nepal Medical Association"},{"key":"15","year":"2011"},{"key":"16","doi-asserted-by":"publisher","DOI":"10.1016\/S0169-409X(96)00423-1"},{"key":"17","year":"2012"},{"key":"18","doi-asserted-by":"publisher","DOI":"10.1021\/jm051031d"},{"key":"19","year":"1990"},{"key":"20","doi-asserted-by":"publisher","DOI":"10.1021\/js980402t"},{"issue":"11","key":"21","doi-asserted-by":"crossref","first-page":"1073","DOI":"10.1592\/phco.31.11.1073","volume":"31","year":"2011","journal-title":"Pharmacotherapy"},{"key":"22","first-page":"1","volume":"10","year":"2004","journal-title":"Clinical Microbiology and Infection"},{"key":"23","doi-asserted-by":"publisher","DOI":"10.2174\/157340610791321442"},{"key":"24"},{"key":"25","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/dkf501"},{"key":"26","doi-asserted-by":"publisher","DOI":"10.1586\/14787210.3.6.907"},{"key":"27","doi-asserted-by":"publisher","DOI":"10.1208\/s12249-010-9552-3"},{"key":"28","doi-asserted-by":"publisher","DOI":"10.1081\/DDC-100101288"},{"issue":"7","key":"29","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1111\/j.2042-7158.1996.tb03949.x","volume":"48","year":"1996","journal-title":"Journal of Pharmacy and Pharmacology"},{"issue":"1","key":"30","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1021\/jm00211a010","volume":"20","year":"1977","journal-title":"Journal of Medicinal Chemistry"},{"key":"31","doi-asserted-by":"publisher","DOI":"10.1002\/qsar.200430866"},{"key":"32","doi-asserted-by":"publisher","DOI":"10.1021\/mp0700209"}],"container-title":["Journal of Pharmaceutics"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/downloads.hindawi.com\/archive\/2013\/517638.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/downloads.hindawi.com\/archive\/2013\/517638.xml","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/downloads.hindawi.com\/archive\/2013\/517638.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2020,12,10]],"date-time":"2020-12-10T13:13:41Z","timestamp":1607606021000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.hindawi.com\/journals\/jphar\/2013\/517638\/"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,5,2]]},"references-count":32,"alternative-id":["517638","517638"],"URL":"https:\/\/doi.org\/10.1155\/2013\/517638","relation":{},"ISSN":["2090-9918","2090-7818"],"issn-type":[{"value":"2090-9918","type":"print"},{"value":"2090-7818","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,5,2]]}}}