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

Brucoli, F., Natoli, A., Marimuthu, P., Borrello, M.T., Stapleton, P.D., Gibbons, S. and Schatzlein, A.G. (2012) Efficient synthesis and biological evaluation of proximicins A, B and C. Bioorganic and Medicinal Chemistry, 20 (6). pp. 2019-2024. 10.1016/j.bmc.2012.01.043.

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DOI: 10.1016/j.bmc.2012.01.043

Abstract

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.

Item Type:Article
Uncontrolled Keywords:Antibiotics; Anticancer molecules; Copper-catalysed amidation; Distamycin and netropsin; DNA-minor groove binding agents
Departments, units and centres:Department of Pharmaceutical and Biological Chemistry > Department of Pharmaceutical and Biological Chemistry
ID Code:3056
Journal or Publication Title:Bioorganic and Medicinal Chemistry
Deposited By:Library Staff
Deposited On:23 Mar 2012 10:51
Last Modified:23 Mar 2012 10:51

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