Complexes R₂Sn(IV)L with Tridentate O,N,O΄-Donor Schiff Bases: Photophysical Properties and Biological Activity

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Abstract

New tin(IV) complexes (Ln)SnR2 (R = n-Bu (I, II), t-Bu (III–V), and Ph (VI)) with O,N,O΄-donor Schiff bases are synthesized. The molecular structures of compounds I and IV in the crystalline state are determined by XRD (CIF files CCDC nos. 2309864 (I) and 2309422 (IV)). The photophysical properties of the complexes are studied in comparison with the previously synthesized compounds containing phenyl or ethyl hydrocarbon groups at the tin atom. All compounds luminesce in chloroform: the emission bands are observed in the range from 580 to 638 nm. Both the groups at the tin atom and nature of the substituents in Schiff bases significantly affect the relative quantum yield. The anti/prooxidant activity of (Ln)SnR2 in the reactions with the ABTS (2,2΄-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)) radical cation and superoxide radical anion, in the oxidative DNA damage, and during lipid peroxidation in vitro is studied. A weak antibacterial activity against the bacterial strains Staphylococcus aureus ANCC 6538 and E. faecium ATCC 3576 are observed for some compounds. The in vitro antiproliferative properties for a number of the complexes are studied for the HTC-116 and А-549 cancer cell lines. The coordination of the organometallic fragment with the O,N,O΄-tridentate ligands is found to induce a pronounced decrease in the cytotoxicity of the complexes.

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About the authors

D. A. Burmistrova

Astrakhan State Technical University

Email: ivsmolyaninov@gmail.com
Russian Federation, Astrakhan

N. P. Pomortseva

Astrakhan State Technical University

Email: ivsmolyaninov@gmail.com
Russian Federation, Astrakhan

K. D. Pashaeva

Astrakhan State Technical University

Email: ivsmolyaninov@gmail.com
Russian Federation, Astrakhan

M. P. Polovinkina

Astrakhan State Technical University

Email: ivsmolyaninov@gmail.com
Russian Federation, Astrakhan

N. R. Al’myasheva

Gause Institute of New Antibiotics, Russian Academy of Medical Sciences

Email: ivsmolyaninov@gmail.com
Russian Federation, Moscow

F. M. Dolgushin

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: ivsmolyaninov@gmail.com
Russian Federation, Moscow

E. D. Tselukovskaya

National Research University Higher School of Economics

Email: ivsmolyaninov@gmail.com
Russian Federation, Moscow

I. V. Anan’ev

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: ivsmolyaninov@gmail.com
Russian Federation, Moscow

O. P. Demidov

North Caucasian Federal University

Email: ivsmolyaninov@gmail.com
Russian Federation, Stavropol

A. I. Poddel’skii

Institute of Inorganic Chemistry, University of Tubingen

Email: ivsmolyaninov@gmail.com
Germany, Tubingen

N. T. Berberova

Astrakhan State Technical University

Email: ivsmolyaninov@gmail.com
Russian Federation, Astrakhan

I. L. Eremenko

Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: ivsmolyaninov@gmail.com
Russian Federation, Moscow

I. V. Smolyaninov

Astrakhan State Technical University

Author for correspondence.
Email: ivsmolyaninov@gmail.com
Russian Federation, Astrakhan

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Supplementary files

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2. Scheme 1.

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3. Fig. 1. Molecular structure of the L²SnᵗBu₂ (IV) complex according to X-ray diffraction data. Hydrogen atoms are not shown. Ellipsoids represent 50% probability.

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4. Fig. 2. Molecular structure of the L¹SnⁿBu₂ (I) complex according to X-ray diffraction data. Hydrogen atoms are not shown. Ellipsoids are 50% probability.

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5. Fig. 3. Electronic absorption spectra of complexes: I (1), II (2), IV (3), V (4) in CHCl₃ at 293 K (c = 3.0 × 10⁻⁵ mol/l).

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6. Fig. 4. Fluorescence spectra of complexes: VI (1), I (2), V (3), IV (4) in CHCl₃ at 293 K (c = 5.0 × 10⁻⁶ mol/L).

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7. Fig. 5. Fluorescence spectra of complexes XI (1), VIII (2), X (3), XIII (4) in CHCl₃ at 293 K (c = 5.0 × 10⁻⁶ mol/L).

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8. Fig. 6. Isosurfaces of some Kohn–Sham molecular orbitals (value |0.02| a.u.) calculated at the B3LYP/def2TZVP level for compound X.

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9. Fig. 7. Electronic absorption spectra of tin(IV) complexes: IV (1); IX (2); X (3) (25°C, 3 h, s = 5 × 10⁻⁶ M) at pH 4.

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10. Fig. 8. Electronic absorption spectra of complex IX at different pH values ​​of the medium (25°C, 3 h, s = 5 × 10⁻⁶ M).

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11. Fig. 9. Changes in the electronic absorption spectra of complex IX over time at pH 7.0 (25°C, 3 h, s = 5 × 10⁻⁶ M).

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12. Fig. 10. Changes in the concentration of TBA-AP in Wistar rat liver homogenates in vitro in the presence of I, III, V–XIII during incubation (3, 24, 48 h) (compound concentration 100 µmol; no additives – control; mean values ​​with standard deviations are presented).

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13. Fig. 11. Change in the absorption of TBA-AP formed as a result of oxidative damage to DNA molecules (2.0 mg ml⁻¹) upon introduction of the AAPG promoter (40 mmol l⁻¹), in the presence of I–XIII (50 µmol), as well as Trolox (control - without added compounds).

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