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Rational Approach Towards Designing Metallogels From a Urea‐Functionalized Pyridyl Dicarboxylate: Anti‐inflammatory, Anticancer, and Drug Delivery
Author(s) -
Sarkar Koushik,
Dastidar Parthasarathi
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801462
Subject(s) - chemistry , solvent , urea , nuclear chemistry , isophthalic acid , molecule , drug delivery , proton nmr , ligand (biochemistry) , combinatorial chemistry , polymer chemistry , stereochemistry , organic chemistry , biochemistry , polyester , terephthalic acid , receptor
A structural rationale was adopted to design a series of metallogels from a newly synthesized urea‐functionalized dicarboxylate ligand, namely, 5‐[3‐(pyridin‐3‐yl)ureido]isophthalic acid ( PUIA ), that produces metallogels upon reaction with various metal salts (Cu II , Zn II , Co II , Cd II , and Ni II salts) at room temperature. The gels were characterized by dynamic rheology and transmission electron microscopy (TEM). The existence of a coordination bond in the gel state was probed by FTIR and 1 H NMR spectroscopy in a Zn II metallogel (i.e., MG2 ). Single crystals isolated from the reaction mixture of PUIA and Co II or Cd II salts characterized by X‐ray diffraction revealed lattice inclusion of solvent molecules, which was in agreement with the hypothesis based on which the metallogels were designed. MG2 displayed anti‐inflammatory response (prostaglandin E 2 assay) in the macrophage cell line (RAW 264.7) and anticancer properties (cell migration assay) on a highly aggressive human breast cancer cell line (MDA‐MB‐231). The MG2 metallogel matrix could also be used to load and release (pH responsive) the anticancer drug doxorubicin. Fluorescence imaging of MDA‐MB‐231 cells treated with MG2 revealed that it was successfully internalized.