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Esterification of Salicylic acid with Succinylated Dextran Using ZrOCl2.8H2O over MCM-41: A Novel Strategy to Design Polysaccharide-Based Macromolecular Prodrugs

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Abstract

We are exploiting the use of a versatile catalyst taken from heterogeneous catalysis, i.e., ZrOCl2.8H2O 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 (ZrOCl2.8H2O) as a catalyst at 80 °C under N2. Reaction conditions and amount of catalyst ZrOCl2.8H2O 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, 1H, and APT-13C 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.

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Authors and Affiliations

  1. Institute of Chemistry, University of Sargodha, Sargodha, 40100, Pakistan

    Muhammad Ajaz Hussain & Saima Iqbal

  2. Department of Horticulture, Ataturk University Agricultural Faculty, 25240, Erzurum, Turkey

    Sezai Ercisli

  3. Department of Chemistry, University of Sahiwal, Sahiwal, Pakistan

    Abdul Hameed

  4. Chemistry Department, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Kingdom of Saudi Arabia

    Muhammad Nawaz Tahir

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  1. Muhammad Ajaz Hussain
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  2. Saima Iqbal
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  3. Sezai Ercisli
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  4. Abdul Hameed
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  5. Muhammad Nawaz Tahir
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Correspondence to Muhammad Ajaz Hussain.

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Hussain, M.A., Iqbal, S., Ercisli, S. et al. Esterification of Salicylic acid with Succinylated Dextran Using ZrOCl2.8H2O over MCM-41: A Novel Strategy to Design Polysaccharide-Based Macromolecular Prodrugs. Arab J Sci Eng 46, 5583–5591 (2021). https://doi.org/10.1007/s13369-020-05143-9

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  • DOI: https://doi.org/10.1007/s13369-020-05143-9

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