Display omitted •Q ⊂ TSCX4 complex was characterized UV fluorescence, 2D NMR, HRMS experiments combined with density functional theory.•Quinoline is held within TSCX4 cavity by CH–--π, π---π and hydrogen bonding interactions as inferred from theory.•1H NMR titration and HRMS experiments ascertain 1:1 stoichiometry for the Q ⊂ TSCX4 complex.•band near 411 nm in fluorescence spectra in water display a blue-shift and significant intensity enhancement.•Bensai-Heildered method yields the binding constant 7.1 x 103 M−1 for the Q ⊂ TSCX4 complex in aqueous phase. The inclusion complex between bowl-shaped para-sulfonatothiacalix4arene (TSCX4) macrocycle and quinoline has been studied with a unison of UV–visible, infra-red, flourescence emission and 1H nuclear magnetic resonance (NMR) and 2D nuclear overhauser effect spectroscopy (NOESY), high resolution mass spectrometry (HRMS) experiments. Both 1H NMR titration and HRMS experiments point to 1:1 stoichiometry for the water soluble Q⊂TSCX4 complex. The electronic structure of the inclusion complex obtained from density functional theory (DFT) showed a partial encapsulation of quinoline guest, which is held within the host cavity by C–H---π, π---π and hydrogen bonding interactions. The fluorescence emission spectra upon complexation display marginal blue shift of the 411 nm band in TSCX4. Moreover, the binding constant (7.1 × 103 M−1) determined from fluoresence emission experiments underline the effective host–guest binding in the complex, which was corroborated through frequency up-shift (‘blue shift’) of characteristic Ar-OH (3433 cm−1) and SO3- vibrations (1141 cm−1 and 1037 cm−1) in the measured infrared spectra of TSCX4. The antiproliferative activitities of the Q⊂TSCX4 complex against HeLA, MDA-MB-231and N2a cells are presented. The Q⊂TSCX4 complex has been shown to be efficient against N2a (neuroblastoma) cell line.