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Hydrophilic meso-substituted cyanine dyes in solution and in complexes with serum albumins: spectral properties and molecular docking study

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Abstract

The absorption and fluorescence spectral properties of three meso-substituted hydrophilic thiacarbocyanine dyes were studied in solutions and in noncovalent complexes with human and bovine serum albumins (HSA and BSA, respectively). The presence of alkyl substituents at the meso-position of the polymethine chain of the dyes determines the occurrence of a cis–trans equilibrium. Dyes form aggregates in aqueous media; the effect of electrolyte (NaCl) on aggregation has been studied. The interaction of the dyes with albumins leads to the decomposition of the aggregates and is accompanied by a shift in the isomeric equilibrium. Complexation with HSA leads to accumulation of dye monomers in the trans-form. However, in the case of BSA the cis-to-trans isomeric shift is incomplete. Using the fluorescence data, the effective binding constants of the trans-isomers with albumins (Ka) and the detection limits of albumin molecules (LD and LQ) were determined. The data obtained are indicative of high selectivity of some dyes to HSA compared to BSA. The results of molecular docking experiments correspond to the data obtained from the spectra. The influence of the dyes on intrinsic fluorescence of HSA and BSA was also studied, and fluorescence quenching, static in nature, was detected.

Graphic abstract

The non-covalent interaction of three thiacarbocyanines with HSA and BSA was studied by spectroscopy techniques and molecular docking. This interaction leads to the accumulation of fluorescent trans-isomers of the dyes. For HSA, high binding constants and low LD/LQ were obtained. Quenching of the intrinsic fluorescence of albumins was studied.

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Notes

  1. Earlier12 we presented a lower value of LDHSA for DMC equal to 7.9 × 10–10 M, which was calculated using the standard relationship Equation S2, which is based on the initial linear portion of the plot. However, the very initial portion of the calibration curve for DMC with HSA was found to be not linear (it is s-shaped, see Figure S9); its deviation from linearity is probably due to occurrence of aggregation-deaggregation phenomena11. So the actual LD value for DMC is somewhat higher than the value calculated from Equation S2.

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Acknowledgements

This work was performed under the Russian Federation State Assignment no. 001201253314. The authors are grateful to Prof. B.I. Shapiro for giving the polymethine dyes. The authors are grateful to Prof. I. G. Plashchina for DLS measurements. Molecular graphics and analyses performed with UCSF Chimera are developed by the Resource for Biocomputing, Visualization, and Informatics at the University of California, San Francisco, with support from NIH P41-GM103311.

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  1. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Kosygin St. 4, Moscow, 119334, Russia

    Pavel G Pronkin, Ludmila A Shvedova & Alexander S Tatikolov

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  1. Pavel G Pronkin
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  2. Ludmila A Shvedova
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  3. Alexander S Tatikolov
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Correspondence to Pavel G Pronkin.

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Equations S1–S5, Figures S1–S21 and Table S1 are available at www.ias.ac.in/chemsci.

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Pronkin, P.G., Shvedova, L.A. & Tatikolov, A.S. Hydrophilic meso-substituted cyanine dyes in solution and in complexes with serum albumins: spectral properties and molecular docking study. J Chem Sci 132, 152 (2020). https://doi.org/10.1007/s12039-020-01858-2

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