New 1-(Spiro[chroman-2,1′-cycloalkan]-4-yl)-1H-1,2,3-Triazoles: Synthesis, QTAIM/MEP analyses, and DNA/HSA-binding assays

This study synthesized and characterized the DNA/HSA properties of a new series of 12 examples of 4-(alkyl/aryl)-1-(spiro[chroman-2,1′-cycloalkan]-4-yl)-1H-1,2,3-triazoles (SCTz), in which alkyl = CH3(CH2)5 and aryl = C6H5, 4-NH2C6H4, 3-OCH3C6H4 (47–95% yield) by regioselective Copper-Catalyzed Azide–Alkyne Cycloaddition (CuAAC) reaction. Additioanally, single crystal X-ray diffraction (SC-XRD) analysis was carried out and the SC-XRD data enabled a broad molecular analysis using QTAIM and MEP analysis. Absorption UV–Vis properties of SCTz series were investigated and all derivatives absorb in the UV region and no are observed emission fluorescence in solution. The DNA-binding assays (UV–Vis analysis) showed that the all spiroderivatives demonstrated strong binding forces to CT-DNA. The Stern-Volmer quenching constants (KSV) of SCTz were calculated and derivatives containing the OCH3 group competed more strongly with DNA minor grooves, followed by the increasing general order of (KSV): EB-DNA < DAPI-DNA. Additionally, the high values observed for the bimolecular quenching constant rate (kq) indicated a static interaction between spiroderivatives and DNA in all cases. Finally, the HSA-binding experiments and molecular docking studies for the new spiroderivatives were determined and quenching (KSV) and quenching rate (kq) constants values obtained for the SCTz suggest good interaction between HSA and derivatives, probably by static mechanism, forming HSA:compound adduct in the ground state.