Acridine based compounds have known to exhibit many biological functions. In the present study N-(acridin-9-yl)alkanamides with octadecyl (9A18), tetradecyl (9A14), and dodecyl (9A12), carbon-chain have been synthesized using stearoyl chloride, lauryl chloride, and myristoyl chloride, respectively. 3<i>β</i>-cholesteryl N-(9-acridinyl) carbamate (9AC) was also prepared by the reaction between 9-aminoacrdine and cholesteryl chloroformate. All synthesized compounds were characterized using spectroscopic and thermal analysis. Gelation and solubility studies of all synthesized compounds have been carried out in various polarity liquids. A 5 wt % 9A12 has been shown to gelate DMSO, silicone oil, and safflower oil, whereas a 5 wt % 9A14 and 9A18 only formed gel in DMSO and silicone oil. Interestingly 5 wt % 9AC did not exhibit gelation property in any of the examined liquids. Correlations between self-assembly and gelation properties of 9-aminoacridine derivatives (9A12, 9A14, 9A18, and 9AC) in 18 different polarity liquids and thermal properties will be presented. Rheology studies of the 5 wt % 9-A18 in silicone oil gel show higher yield strain and storage modulus compared to a 5 wt % 9-A12 in silicone oil gel.and the gels are weakly thixotropic. Computational docking studies of complexation with DNA shows that 9AC binds DNA strongly compared to pyridinyl cholesteryl carbamate or 9-aminoacridine. The computed affinities for each ligand 9 AC, 3<i>β</i>-cholesteryl N-(9-pyridinyl) carbamate, 9-aminoacridine, and 4-aminopyridine are 17.34, -16.00, -12.60, and -7.38 kcal/mol respectively.

Synthesis, self-assembly, gelation, and DNA binding molecular docking studies of 9-aminoacridine derivatives

ACS Spring Meeting 2021

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