Esterification of Salicylic acid with Succinylated Dextran Using ZrOCl2.8H(2)O over MCM-41: A Novel Strategy to Design Polysaccharide-Based Macromolecular Prodrugs


Hussain M. A., Iqbal S., ERCİŞLİ S., Hameed A., Tahir M. N.

ARABIAN JOURNAL FOR SCIENCE AND ENGINEERING, cilt.46, sa.6, ss.5583-5591, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 46 Sayı: 6
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1007/s13369-020-05143-9
  • Dergi Adı: ARABIAN JOURNAL FOR SCIENCE AND ENGINEERING
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aerospace Database, Communication Abstracts, Metadex, Pollution Abstracts, zbMATH, Civil Engineering Abstracts
  • Sayfa Sayıları: ss.5583-5591
  • Anahtar Kelimeler: Esterification, Salicylate, Succinylation, Zirconium (IV) oxychloride octahydrate (ZrOCl2, 8H(2)O), Macromolecular prodrugs, POLYMERIC DRUG CARRIERS, IN-VITRO, ASPIRIN, SALICYLANILIDES, INHIBITORS, RELEASE, ESTERS
  • Atatürk Üniversitesi Adresli: Evet

Özet

We are exploiting the use of a versatile catalyst taken from heterogeneous catalysis, i.e., ZrOCl2.8H(2)O to efficiently catalyze the reaction of dextran-succinate conjugate (Dex-SAn) with salicylic acid (SA) under homogeneous reaction conditions. Dextran was first linked with succinic anhydride using triethylamine as a base in DMAc to provide active functionalities (succinate moieties) situated away from the polymer chains. The resultant Dex-SAn conjugate was further esterified with SA using zirconium (IV) oxychloride octahydrate (ZrOCl2.8H(2)O) as a catalyst at 80 degrees C under N-2. Reaction conditions and amount of catalyst ZrOCl2.8H(2)O and chiral support MCM-41 were optimized. This reaction methodology resulted in macromolecular prodrugs of SA as Dex-SAn-SA conjugates in good yield. The structures of Dex-SAn and newly synthesized Dex-SAn-SA conjugates were characterized using various spectroscopic techniques, i.e., FT-IR, H-1, and APT-C-13 NMR spectroscopy. The degree of substitution of SA on to Dex-SAn-SA was determined by UV/Vis spectroscopic methods. This reaction methodology can be modeled as a new protocol for facile attachment of several drug molecules onto the highly potential and biodegradable drug carrier dextran.