| Ferrocenyl bioconjugates of ampicillin and 6-aminopenicillinic acid - Synthesis, electrochemistry and biological activity. | |
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MedLine Citation:
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PMID: 23072737 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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We report on the synthesis of ferrocenyl-ampicillin and ferrocenyl-6-aminopenicillinic acid bioconjugates. Title compounds were characterized by (1)H NMR, IR, MS and elemental analysis. These novel ferrocenyl-antibiotic conjugates were also investigated by cyclic voltammetry (CV). Ferrocenyl-ampicillin complexes revealed reversible uncomplicated oxidation whereas ferrocenyl-6-aminopenicillinic acid derivatives were found to exhibit adsorption waves in cathodic scans. Antibacterial activities of our ferrocenyl-antibiotic conjugates against Gram-positive methicillin-sensitive Staphylococcus aureus (MSSA), methicillin-resistant S.aureus (MRSA), vancomycin-resistant S.aureus (VRSA) and Staphylococcus epidermidis bacterial strains were determined. Our experiments show significant antibacterial activity of ferrocenyl-6-aminopenicillinic acid bioconjugates against the bacterial strains tested. Contrary to that ferrocenyl-ampicillin derivatives were inactive. The inhibitory effects on the dd-carboxypeptidase 64-575 II exerted by our ferrocenyl-6-aminopenicillinic acid bioconjugates were established in the low nanomolar range. The tumor cell growth inhibition of representative ferrocenyl-ampicillin and ferrocenyl-6-aminopenicillinic acid bioconjugates against MCF-7 breast adenocarcinoma and HT-29 colon carcinoma cell lines were studied in vitro. Similar to the antibacterial activity tests the assays in tumor cells revealed significant antiproliferative effects exerted by ferrocenyl-6-aminopenicillinic acid bioconjugates. |
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Authors:
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Joanna Skiba; Aleksandra Rajnisz; Kely Navakoski de Oliveira; Ingo Ott; Jolanta Solecka; Konrad Kowalski |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-9-23 |
Journal Detail:
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Title: European journal of medicinal chemistry Volume: 57C ISSN: 1768-3254 ISO Abbreviation: Eur J Med Chem Publication Date: 2012 Sep |
Date Detail:
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Created Date: 2012-10-17 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0420510 Medline TA: Eur J Med Chem Country: - |
Other Details:
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Languages: ENG Pagination: 234-239 Citation Subset: - |
Copyright Information:
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Copyright © 2012 Elsevier Masson SAS. All rights reserved. |
Affiliation:
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Department of Organic Chemistry, Faculty of Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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