title: β-Amino acid and amino-alcohol conjugation of a nonsteroidal anti-inflammatory drug (NSAID) imparts hydrogelation displaying remarkable biostability, biocompatibility, and anti-inflammatory properties.
abstract: A well-known nonsteroidal anti-inflammatory drug (NSAID), namely, naproxen (Np), was conjugated with β-alanine and various combinations of amino alcohols and l-alanine. Quite a few bioconjugates, thus synthesized, were capable of gelling pure water, NaCl solution (0.9 wt %), and phosphate-buffered saline (PBS) (pH 7.4). The hydrogels were characterized by rheology and electron microscopy. Hydrogelation was probed by FT-IR and temperature-variable (1)H NMR studies. Single-crystal X-ray diffraction (SXRD) of a nonhydrogelator and a hydrogelator in the series established a useful structure-property (gelation) correlation. MTT assay of the hydrogelators in the mouse macrophage RAW 264.7 cell line showed excellent biocompatibility. The prostaglandin E2 (PGE2) assay of the hydrogelators revealed their anti-inflammatory response, which was comparable to that of the parent NSAID naproxen sodium (Ns).
authors.affiliation: Department of Organic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Kolkata-700032, India.
authors.forename: Joydeb
authors.initials: J
authors.lastname: Majumder
authors.forename: Mahua Rani
authors.initials: MR
authors.lastname: Das
authors.forename: Jolly
authors.initials: J
authors.lastname: Deb
authors.forename: Siddhartha Sankar
authors.initials: SS
authors.lastname: Jana
authors.forename: Parthasarathi
authors.initials: P
authors.lastname: Dastidar
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001672:Biocompatible Materials / Q000737:chemistry*; D002460:Cell Line; D015232:Dinoprostone / Q000037:antagonists & inhibitors / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D020100:Hydrogels / Q000737:chemistry*; D007371:Interferon-gamma / Q000037:antagonists & inhibitors / Q000378:metabolism; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D010316:Particle Size; D013499:Surface Properties
chemical_list: D000596:Amino Acids; D000605:Amino Alcohols; D000894:Anti-Inflammatory Agents, Non-Steroidal; D001672:Biocompatible Materials; D020100:Hydrogels; D008070:Lipopolysaccharides; D007371:Interferon-gamma; D015232:Dinoprostone