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Issue 68, 2015
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Synthesis, characterization and biological evaluation of chromen and pyrano chromen-5-one derivatives impregnated into a novel collagen based scaffold for tissue engineering applications

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Abstract

In this article, we describe the synthesis and biological evaluation of a novel 2-(methylamino)-3-nitro-4-(4-oxo-4H-chromen-3-yl) pyrano[3,2-c]chromen-5(4H)-one (CCN). It is also determined that CCN impregnated into the collagen scaffold has the potential to mimic the function of the extracellular matrix as a biomaterial in the field of tissue engineering. The series of pyrano[3,2-c]chromen-5(4H)-one derivatives (4a–4j), was analyzed by 1H NMR, 13C NMR, mass spectra and FTIR analysis. Compound 4c was confirmed by single crystal XRD studies. All the compounds were screened for antimicrobial activity against Gram positive, Gram negative bacteria and yeast. Among all the compounds, compound (4a[double bond, length as m-dash]CCN) showed activity against Gram positive and Gram negative bacteria, when compared to the synthesized compounds. Further, compound CCN was evaluated for cytotoxicity against MCF-7, Hep-2 and Vero cancer cell lines with IC50 values of 5.4 μg ml−1, 5.3 μg ml−1 and 68.4 μg ml−1 respectively. In addition, the results of flow cytometry and docking (PDBID: 1A27 with the ligand) studies supported the activity of the synthesized compound (4a). FTIR and NMR analysis of the CCN impregnated collagen scaffold were done to reveal the existence of the CCN molecule in the scaffold. The inherent property of the collagen scaffold was not significantly affected by the structure of the CCN molecule. The thermal and mechanical properties of the collagen scaffold impregnated with CCN molecules gives stability as well as supports the swelling. However, the COL-CCN scaffold showed an enhanced cell attachment and proliferation of NIH 3T3 fibroblast cells. Based on the results, the novel CCN molecule impregnated within a collagen scaffold has potential application as a biomaterial in tissue engineering.

Graphical abstract: Synthesis, characterization and biological evaluation of chromen and pyrano chromen-5-one derivatives impregnated into a novel collagen based scaffold for tissue engineering applications

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Supplementary files

Article information


Submitted
20 Apr 2015
Accepted
09 Jun 2015
First published
12 Jun 2015

RSC Adv., 2015,5, 55075-55087
Article type
Paper
Author version available

Synthesis, characterization and biological evaluation of chromen and pyrano chromen-5-one derivatives impregnated into a novel collagen based scaffold for tissue engineering applications

S. Kandhasamy, G. Ramanathan, J. Kamalraja, R. Balaji, N. Mathivanan, U. T. Sivagnanam and P. T. Perumal, RSC Adv., 2015, 5, 55075
DOI: 10.1039/C5RA07133J

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