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Polymer-drug conjugates based on a new 6-amino penicillanic acid derivative

D. DUMITRAS1,* , M. POPA1, V. SUNEL2, L. VERESTIUC3

Affiliation

  1. “Gh. Asachi’’ Technical University of Iasi, Faculty of Chemical Engineering, Department of Natural and Synthetic Polymers, Bd. D. Mangeron 71 A, 700050 Iasi, Romania
  2. ”Al. I. Cuza” University of Iasi, Department of Organic Chemistry, Bd. Copou 11, 700506, Iasi, Romania
  3. “Gr. T. Popa” University of Medicine and Pharmacy, Faculty of Medical Bioengineering, Str. Universitatii nr. 16 700115, Iasi, Romania

Abstract

The paper presents the synthesis of new bioconjugate based on gellan and a 6-amino penicillanic acid derivative as a material with controlled release properties. Drug have been obtained by the decycling of 2-(m-nitrophenyl)-4-(β- carboxyethyl)-Δ2-oxazolinone-5 with 6-amino-penicillanic acid (6-APA) and the product (Ox-Pen) immobilization on polysaccharides (gellan, xanthane, carboxymethyl cellulose sodium salt, sodium alginate) by using esteric bonds forming, in presence of dicyclohexyl carbodiimide (DCCI) as activator. N-(m-nitrobenzoyl)-α-L-glutamyl-penicilline (Ox-Pen), as well as immobilization products, have been characterized by elemental analysis, IR and NMR spectroscopy and toxicity (lethal doses, LD50). For the gellan-active principle conjugate (the system with the highest percentage of immobilised drug, obtained by using a centered, rotator, composed, second order experimental program), there was calculated the regression equation describing the dependence of the amount of drug chemically bonded to the support on the reaction parameters. The efficiency of the immobilisation reaction is maximal at 1.5 mol/mol molar ratio DCCI/Ox-Pen, long reactions’ duration, and lower molar ratio support/drug (1:5 mol/mol) respectively. The release kinetics of the active from the polymer-drug system, under alkaline hydrolyses conditions, has been studied too..

Keywords

Drug-polysaccharide conjugate, Penicillin, Biological activity, Controlled release.

Submitted at: March 23, 2007
Accepted at: Nov. 16, 2007

Citation

D. DUMITRAS, M. POPA, V. SUNEL, L. VERESTIUC, Polymer-drug conjugates based on a new 6-amino penicillanic acid derivative, Journal of Optoelectronics and Advanced Materials Vol. 9, Iss. 11, pp. 3466-3473 (2007)