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A Joint Theoretical and Experimental Study of the Behavior of the DIDS Inhibitor and its Derivatives
Author(s) -
JaunetLahary Titouan,
Goupille Anaïs,
Jacquemin Denis,
Fleury Fabrice,
Graton Jérôme,
Laurent Adèle D.
Publication year - 2016
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201600107
Subject(s) - protonation , dids , density functional theory , chemistry , solvation , absorption (acoustics) , computational chemistry , solvent , chemical physics , ion , organic chemistry , physics , optics , biochemistry , membrane
4,4′‐Diisothiocyanostilbene‐2,2′‐disulfonic acid (DIDS) is a well‐known ion‐exchange inhibitor targeting cardiac functions and indirectly impeding both radio‐ and chemo‐resistance. A joint computational and experimental study is presented to provide deeper insights into DIDS and other members of this family of compounds. To this end, we applied state‐of‐the‐art density functional theory (DFT) and time‐dependent DFT methods, in addition to measuring the optical properties. The experimental data show that such compounds are highly sensitive to their environment and that the optical properties change within as little time as 7 h. However, the optical properties of DIDS are similar in various acidic/basic environments, which were confirmed by p K a computations on both cis and trans isomers. The protonation analysis also highlights that the singly protonated form of DIDS behaves like a proton sponge compound. The experimentally observed redshift that can be seen when going from water to DMSO was reproduced solely by using the solvation model based on density, although the polarization continuum model and implicit/explicit hybrid schemes were also tested. The characteristic broadening of the absorption peak in water and the vibronic fine structure in DMSO were also reproduced thanks to vibronic coupling simulations associated with the solvent reorganization energy. For other stilbene derivatives, a correlation is found between the maximum absorption wavelength and the Hammett parameters.