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Supramolecular Synthon Approach in Developing Anti‐Inflammatory Topical Gels for In Vivo Self‐Delivery
Author(s) -
Roy Rajdip,
Dastidar Parthasarathi
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703850
Subject(s) - synthon , hydroxymethyl , tris , chemistry , in vivo , ammonium acetate , nuclear chemistry , supramolecular chemistry , polymer chemistry , organic chemistry , crystal structure , biochemistry , high performance liquid chromatography , microbiology and biotechnology , biology
A new series of tertiary‐butyl ammonium ( TBA ) salts of various nonsteroidal anti‐inflammatory drugs (NSAIDs) have been synthesized and characterized. Nearly 90 % of the NSAID‐derived primary ammonium monocarboxylate (PAM) salts displayed remarkable gelation ability with various solvents including methyl salicylate. Single crystal X‐ray diffraction data (SXRD) revealed the existence of 1D PAM synthon in the gelator salts. Structure–property correlation studies based on SXRD and powder X‐ray diffraction (PXRD) data established the presence of the 1D PAM synthon in the bulk salts as well as in the corresponding xerogels. A parallel series of salts derived from TRIS (2‐amino‐2‐(hydroxymethyl)‐1,3‐propanediol) and the same set of NSAIDs displayed poor gelation ability; only 33 % of the salts in the series displayed gelation ability. A few selected gelator salts of both TBA and TRIS were found to be biocompatible (MTT assay with RAW 264.7 cell line) and two of the selected salts ( FLR.TBA and FLR.TRIS ) possessed anti‐inflammatory properties equal to the parent drug FLR (flurbiprofen). Finally a methyl salicylate topical gel derived from FLR.TRIS was successfully delivered in a self‐delivery fashion to treat inflamed skin conditions in the mice model. Histological studies of the dorsal tissues of the untreated and treated mice clearly demonstrated the effect of topical gels in such treatment.