Efficient synthesis and biological evaluation of proximicins A, B and C.

A quick and efficient synthesis and the biological evaluation of promising antitumor-antibiotics proximicins A, B and C are reported. The characteristic repetitive unit of these molecules, the methyl 4-Boc-aminofuran-2-carboxylate 15, was prepared in three synthetic steps in good yield using an optimised copper-catalysed amidation method. The proximicins were evaluated for their antitumor activity using cellular methods. Proximicin B induced apoptosis in both Hodgkin's lymphoma and T-cell leukemia cell lines and proximicin C exhibited significantly high cytotoxicity against glioblastoma and breast carcinoma cells. The proximicins were also screened against Escherichia coli, Enterococcus faecalis and several strains of methicillin-and multidrug-resistant Staphylococcus aureus. Proximicin B showed noteworthy activity against antibiotic-resistant Gram-positive cocci.
AuthorsFederico Brucoli, Antonino Natoli, Preethi Marimuthu, Maria Teresa Borrello, Paul Stapleton, Simon Gibbons, Andreas Schätzlein
JournalBioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 20 Issue 6 Pg. 2019-24 (Mar 15 2012) ISSN: 1464-3391 [Electronic] England
PMID22364744 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2012 Elsevier Ltd. All rights reserved.
Chemical References
  • Anti-Bacterial Agents
  • Antibiotics, Antineoplastic
  • proximicin A
  • proximicin B
  • proximicin C
  • Netropsin
  • Anti-Bacterial Agents (chemical synthesis, pharmacology)
  • Antibiotics, Antineoplastic (chemical synthesis, pharmacology)
  • Apoptosis (drug effects)
  • Bacterial Infections (drug therapy)
  • Cell Line, Tumor
  • Enterococcus faecalis (drug effects)
  • Escherichia coli (drug effects)
  • Female
  • Humans
  • Methicillin-Resistant Staphylococcus aureus (drug effects)
  • Microbial Sensitivity Tests
  • Neoplasms (drug therapy)
  • Netropsin (analogs & derivatives, chemical synthesis, pharmacology)
  • Staphylococcus aureus (drug effects)

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