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Synthesis and spectroscopic characterization of fluorescent 4-aminoantipyrine analogues: Molecular docking and in vitro cytotoxicity studies.
- Source :
-
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy [Spectrochim Acta A Mol Biomol Spectrosc] 2016 Jan 15; Vol. 153, pp. 118-23. Date of Electronic Publication: 2015 Aug 10. - Publication Year :
- 2016
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Abstract
- Two substituted aromatic carbonyl compounds (compounds 1 and 2) of 4-aminoantipyrine were synthesized by condensation of fluorine substituted benzoyl chlorides and 4-aminoantipyrine. The structures of synthesized derivatives were established on the basis of UV-Vis, IR, and Mass, (1)H, (13)C NMR and Fluorescence spectroscopy. Both compounds showed significant fluorescence emission and two broad emission bands were observed in the region at 340 nm and 450 nm on excitation at 280 nm. Theoretically to prove that the molecule has anticancer activity against cervical cancer cells, the compounds were analyzed for molecular docking interactions with HPV16-E7 target protein by Glide protocol. Furthermore, 4-aminoantipyrine derivatives were evaluated for their in vitro cytotoxic activity against human cervical cancer cells (SiHa) by MTT assay. Compound 1 showed two fold higher activity (IC50=0.912 μM) over compound 2, and its activity was similar to that of Pazopanib, suggesting that although the two compounds were chemically very similar the difference in substituent on the phenyl moiety caused changes in properties.<br /> (Copyright © 2015 Elsevier B.V. All rights reserved.)
- Subjects :
- Ampyrone analogs & derivatives
Ampyrone chemistry
Antineoplastic Agents pharmacology
Cell Line, Tumor
Fluorescence
Humans
Inhibitory Concentration 50
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Conformation
Reference Standards
Spectrometry, Fluorescence
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
Ampyrone chemical synthesis
Ampyrone pharmacology
Molecular Docking Simulation
Subjects
Details
- Language :
- English
- ISSN :
- 1873-3557
- Volume :
- 153
- Database :
- MEDLINE
- Journal :
- Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy
- Publication Type :
- Academic Journal
- Accession number :
- 26298678
- Full Text :
- https://doi.org/10.1016/j.saa.2015.08.008