Discipline: Chemistry and Chemical Sciences
Subcategory: Biochemistry (not Cell and Molecular Biology and Genetics)
Ja'Nautica J. Bee - Tougaloo College
Co-Author(s): Chirantan Sen Mukherjee, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, India; Sandipan Chakrabarty, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, India; Bidisha Sengupta, Tougaloo College, Jackson,MS; George Armstrong Tougaloo College, Jackson,MS;
In this study, microwave irradiation has been used to synthesize an optically active alkylated aniline namely 2,6-dimethyl-4-(1-(p-tolyl)ethyl)aniline (abbreviated DMPA). Despite the fact that aniline, heterocyclic aromatic amines, and arylamines are known carcinogens, aniline mustard has come into prominence recently as novel anticancer agent. With this in mind, we hypothesized that DMPA would be a potential candidate for therapeutic drugs. The presence of quartet and doublet peaks in NMR and a single chromatogram in the HPLC verified that the final product DMPA, prepared from the synthesis reactions, had no major impurities. By using a Lux chiral column in HPLC, two peaks has been detected in the chromatogram, which correspond to two enantiomers of the chiral aniline derivative. Fluorescence spectroscopic measurements on DMPA indicated conspicuous dependence of its emission behavior on the polarity (in terms of the empirical polarity parameter ET(30)) of the homogeneous solvents used, a property important for an optical sensor. The nature of the emission profiles, along with the relevant parameter namely wavelength at emission maximum ( ) is used to infer the distribution, binding and microenvironment of the DMPA molecules in human serum albumin protein (HSA). DMPA is weakly fluorescent in aqueous buffer medium, with a dramatic enhancement in the fluorescence emission in the presence of HSA, with no structural alterations of the protein. Molecular modeling studies have been carried out on the two enantiomers (R and S) of DMPA with HSA which showed selectivity of one enantiomer over the other toward binding with HSA. These results attribute to two aspects of DMPA: 1. Noninvasiveness and 2. Fluorescence sensing capabilities, which would open a new avenue in medicinal chemistry research.
Funder Acknowledgement(s): Institutional Development Award (IDeA) from the National Institute of General Medical Sciences of the National Institutes of Health under grant number P20GM103476.
Faculty Advisor: Bidisha Sengupta, firstname.lastname@example.org
Role: I was the only research student so I was responsible for fluorescence measurements, HPLC, and autodocking. This responsibility helped me to display the validity of my data and results! I've been working on this research for a year. It is still my current research.