Drug Delivery & Targeting (Track)

Synthesis and Biological activity of a Novel Class of Aziridinyl Peptidomimetic as Intersting Antibacterial and Anticancer Agents.

A.Keniche
Laboratoire de Chimie Organique, Substances Naturelles et Analyses (COSNA),Université Aboubakr Belkaid-Tlemcen, B.P. 119 Tlemcen 13 000/Algérie

Abstract:

Despite the difficulty to convert them into orally available drugs, peptidomimetics still constitute a challenging field for investigators. Therefore, many valuable synthetic approaches are found in the literature with an aim to improve either the solubility or the stability of the new compounds towards gastrointestinal hydrolases (1). During a previous work we developed an original approach to have aziridines from amino acids ⁽²⁾. The novel compounds revealed to be endowed with interesting biological properties against breast tumors cells (2,3).

We report here the synthesis of a novel class of aziridines and phosphonoaziridinyl peptides as interesting building blocks that can be thermally opened and reacted with dipolarophiles to obtain functionalized imidazolines and oxazolidines.

Preliminary biological evaluation showed that the novel compounds displayed a good antibacterial activity against Escherichia coli, Staphylococus aureus, Pseudomonas aeruginosa, and Enterococcus faecalis, strains that withstand at present treatment common with antibiotics. 

The whole of our results enable us to modulate the biological activity of this class of aziridines by means of functional groups that may be present. We believe our original approach is of interest as it can furnish antiviral and antibacterial agents at a time when antibiotics are poor to treat novel infections or resurgent ones.

Fig (1) : Structures of aziridines.

Key words:  Aziridines, phosphonat, peptidomimetic, cancer.   

References :

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2. W. Medjahed, A. Tabet Zatla, J. Kajima Mulengi, F.Z. Baba Ahmed, H. Merzouk Tetrahedron Lett., 2004, 45, 1211-1213
   
   
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