Synthesis and Characterization of Poly(lactic-co-glycolic acid) Derived with LGlutamic Acid and L-Aspartic Acid

Poli(laktik-ko-glikolik asit) sağlık alanında en çok kullanılan, biyouyumlu, biyobozunur özellikte FDA ve EMA onaylı bir polimerdir. Bu çalışmada öncelikle polikondenzasyon ve halka açılma polimerizasyonu ile laktid ve glikolidden PLGA sentezlenmiştir. Daha sonra PLGA ve amino asitlerin 1-etil-3-(3-dimetilaminopropil)karbodiimid (EDC) varlığında reaksiyonu ile PLGA'nın amino asit türevleri sentezlenmiştir. Sentezlenen polimerler PLGA, PLGA-L-glutamik asit (PLGA-G) ve PLGA-L-aspartik asit (PLGA-A)'dir. Bu polimerlerin kimyasal yapısı 1H ve 13C Nükleer Manyetik Rezonans (1H NMR ve 13C NMR), Fourier Dönüşümlü Kızılötesi Spektroskopisi (FTIR), Diferansiyel Taramalı Kalorimetri (DSC) ve Jel Geçirgenlik Kromatografisi (GPC) ile doğrulandı. PLGA-amino asit türevlerinin 13C NMR analizleri incelendiğinde 170 ppm yakınlarında karbonil karbonlarının sayısında artış gözlenerek yapı doğruluğu desteklenmiştir. Ayrıca yine PLGA-amino asit türevlerinin FTIR analizleri incelendiğinde amid bağı karbonil titreşimine ait sinyal 1700 cm-1'de gözlenerek yapı doğrulanmıştır. PLGA-aminoasit türev yapılarının DSC analizi ile tipik endotermik termogram gözlenirken, GPC analizleri ile yapıların düşük molekül ağırlıklı polimerler [~5000-6000 Da] olduğu gösterilmiştir.

Anahtar Kelimeler:

PLGA, amino asit, biyobozunur polimer

Synthesis and Characterization of Poly(lactic-co-glycolic acid) Derived with LGlutamic Acid and L-Aspartic Acid

Poly(lactic-co-glycolic acid) (PLGA) is a biocompatible, biodegradable polymer approved by the FDA and EMA, which is the most widely used in the field of health. In this study, PLGA was synthesized primarily from lactide and glycolide by polycondensation and ring-opening polymerization. Then, amino acid derivatives of PLGA were synthesized by the reaction of PLGA and amino acids in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC). The polymers synthesized were PLGA, PLGA-L-glutamic acid (PLGA-G), and PLGA-L-aspartic acid (PLGA-A). The chemical structure of these polymers was confirmed by 1H and 13C Nuclear Magnetic Resonance (1H NMR and 13C NMR), Fourier Transform Infrared Spectroscopy (FTIR), Differential Scanning Calorimetry (DSC), and Gel Permeation Chromatography (GPC). When the 13C NMR analyses of PLGA-amino acid derivatives were observed, an increase in the number of carbonyl carbons around 170 ppm was found and the structure accuracy was supported. In addition, when the FTIR analyses of PLGA-amino acid derivatives were examined, the structure was confirmed by observing the signal of the amide bond carbonyl vibration at 1700 cm-1. While the typical endothermic thermogram of the PLGA-amino acid derivative structures was observed by DSC analysis, it was shown that the structures were low molecular weight polymers [~5000-6000 Da] by GPC analysis.

Keywords:

PLGA, amino acid, biodegradable polymer,

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