Crystal Structure, quantum chemical analysis and apoptotic propensity of diaryl substituted α-aminophosphonates as selected C[sbnd]P bonded systems.

[Display omitted] Multi segmented work on sonochemical synthesis of supra decorated α-aminophosphonates as C P bonded representatives, from comprehensive crystal structure analysis to solid state properties and anticancer activity evaluation. Bench marked computational methodology for evaluation of quantum chemical descriptors for prediction of electronic structure and reactivity. Three component Kabachnik-Fields reaction under sonochemical conditions was utilized for synthesizing library of electronically diverse aryl substituted α-aminophosphonates as representative carbon phosphorus bonded systems. Single crystal X-ray structures of four novel α-aminophosphonate derivatives with comprehensive Hirshfeld surface analysis for highlighting influence of different functionalities over α-aminophosphonate motif on the crystal packing pattern and formation of molecular assemblies via supramolecular aggregation have been presented. Solid state absorption and photoluminescence studies corroborated electronic and crystal packing influences. The computational methodologies for evaluating quantum chemical descriptors of electronic properties of α-aminophosphonates were bench marked. The bioactivity potential of synthesized library of α- aminophosphonates was evaluated from their cytotoxic propensity towards human cancer lines in NCI-60 panel via SRB assay. The screened derivatives showed a range of cytotoxicity against cancer cell lines in NCI-60 panel. Compound 3 exhibited highest cell growth inhibition in prostate cancer cells with IC 50 value of 10.94 μM. For mechanistic insights apoptotic propensity was evaluated using caspase-3 enzyme assay in PC-3 cells. The onset of apoptosis via caspase-3 activation was evidenced as a major pathway from morphological changes under fluorescence microscope with and without DAPI staining. The triggering of apoptosis via caspase 3 activation by the lead compound 3 was also confirmed from western blot analysis of PARP-1 in PC-3 cancer cells. Furthermore, the anti-metastatic potential of compound 3 can be predicted from its efficacy in restricting the migration of PC-3 cancer cells under in vitro conditions observed from wound healing assay. [ABSTRACT FROM AUTHOR]