Medium viscosity effect on fluorescent properties of Sn(IV)-tetra(4-sulfonatophenyl)porphyrin complexes in buffer solutions

Мамардашвили, Г. М.; Maltceva, Olga V.; Lazovskiy, Dmitriy A.; Khodov, Ilya A.; Borovkov, Victor; Мамардашвили, Н. Ж.; Койфман, О. И.

doi:10.1016/j.molliq.2018.12.118

Cited by 23 publications

(8 citation statements)

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“…Diffusion-ordered spectroscopy (DOSY) was used to determine the composition of the reaction (1) products between Sn(IV)-porphyrin axial complexes and Cu 2+ . It has been reported in recent works [ 30 , 49 , 50 , 51 , 52 , 53 , 54 ] that this method is among the most effective in the analysis of supramolecular complexes of macrocyclic compounds. This method makes it possible to confirm the structures of the formed supramolecular complexes by comparing the diffusion coefficients of the systems obtained by self-assembly with the diffusion coefficients of the initial compounds (before the self-assembly) taken as objects of comparison.…”

Section: Resultsmentioning

confidence: 99%

“…Bis -thyrazine-Sn(IV)-5,10,15,20-tetra(4-sulfonatophenyl)porphyrin (I) was obtained according to the procedure described by us previously in [ 30 ] from the bis-hydroxy-Sn(IV)-5,10,15,20-tetra(4-sulfonatophenyl)porphyrin (III). Mass-spectrum (MALDI-TOF): (m/z):[M+H] + 1407.17; molecular formulaC 62 H 46 N 6 O 18 S 4 Sn-requires [M] + 1406.01;UV-Vis (H 2 O), λ nm (lgε): 594 (4.06), 555 (3.57), 421 (5.04), 1 HNMR (500 MHz, D 2 O), ppm: 9.41 (s, 8H, Hβ-pyr.…”

Section: Methodsmentioning

confidence: 99%

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New Polyporphyrin Arrays with Controlled Fluorescence Obtained by Diaxial Sn(IV)-Porphyrin Phenolates Chelation with Cu2+ Cation

et al. 2021

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New coordination oligomers and polymers of Sn(IV)-tetra(4-sulfonatophenyl)porphyrin have been constructed by the chelation reaction of its diaxialphenolates with Cu2+. The structure and properties of the synthesized polyporphyrin arrays were investigated by 1H Nuclear Magnetic Resonance (1H NMR), Infra Red (IR), Ultra Violet - Visible (UV-Vis) and fluorescence spectroscopy, mass spectrometry, Powder X-Rays Diffraction (PXRD), Electron Paramagnetic Resonance (EPR), thermal gravimetric, elemental analysis, and quantum chemical calculations. The results show that the diaxial coordination of bidentate organic ligands (L-tyrazine and diaminohydroquinone) leads to the quenching of the tetrapyrrole chromophore fluorescence, while the chelation of the porphyrinate diaxial complexes with Cu2+ is accompanied by an increase in the fluorescence in the organo-inorganic hybrid polymers formed. The obtained results are of particular interest to those involved in creating new ‘chemo-responsive’ (i.e., selectively interacting with other chemical species as receptors, sensors, or photocatalysts) materials, the optoelectronic properties of which can be controlled by varying the number and connection type of monomeric fragments in the polyporphyrin arrays.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

New Polyporphyrin Arrays with Controlled Fluorescence Obtained by Diaxial Sn(IV)-Porphyrin Phenolates Chelation with Cu2+ Cation

et al. 2021

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“…The complexes Co(III)P(1-2) are characterized by a higher relative value of the self-diffusion coefficient to the solvent (0.39), than the complexes with ligands (0.34 and 0.28), which confirms the changes of molecular mass as a result of the complex formation. In addition to this, Co(III)P2 and Co(III)P2-L2, and Co(III)P2-L3 complexes were completely characterized by means of two-dimensional correlation spectroscopy (1H–1H 2D of COSY), which also is applied for the determination of macromolecules chemical structure [ 17 , 30 , 31 , 32 , 33 , 34 , 35 ].…”

Section: Results and Its Discussionmentioning

confidence: 99%

“…The lengths of the formed hydrogen bond and the energies of the intermolecular interaction of the bis-axial complex are in good agreement with the values of the energies of hydrogen bonds determined from the formation constants of the Co(III)P-(L)(H2O) complexes ( Figure 5). For the analysis of the chemical structure of Со(III)P(1-2)and its complexes with L1-L3, 1 H NMR spectrawere obtained as shown in the Figure 4, which are thesuperposition (convolution) of spectra, relating to a certainrange of self-diffusion coefficients, which thesebonds are characterized [17,[27][28][29][30][31]. Such superposition is obtainedby a projection of a pseudo-two-dimensional spectrum ofthe diffusive ordered DOSY spectroscopy on the set rangeof self-diffusion coefficients.…”

Section: Co(iii)p and Lmentioning

confidence: 99%

Molecular Recognition of Imidazole Derivatives by Co(III)-Porphyrins in Phosphate Buffer (pH = 7.4) and Cetylpyridinium Chloride Containing Solutions

et al. 2021

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Bymeans of spectrophotometric titration and NMR spectroscopy, the selective binding ability ofthe Co(III)-5,15-bis-(3-hydroxyphenyl)-10,20-bis-(4-sulfophenyl)porphyrin (Со(III)Р1) andCo(III)-5,15-bis-(2-hydroxyphenyl)-10,20-bis-(4-sulfophenyl)porphyrin (Со(III)Р2) towards imidazole derivatives of various nature (imidazole (L1), metronidazole (L2), and histamine (L3)) in phosphate buffer (pH 7.4) has been studied. It was found that in the case of L2, L3 the binding of the “first” ligand molecule by porphyrinatesCo(III)P1 and Co(III)P2 occurs with the formation of complexes with two binding sites (donor–acceptor bond at the center and hydrogen bond at the periphery of the macrocycle), while the “second” ligand molecule is added to the metalloporphyrin only due to the formation of the donor–acceptor bond at the macrocycle coordination center. The formation of stable complexes with two binding sites has been confirmed by density functional theory method (DFT) quantum chemical calculations and two-dimensional NMR experiments. It was shown that among the studied porphyrinates, Co(III)P2 is more selective towards to L1-L3 ligands, and localization of cobalt porphyrinates in cetylpyridinium chloride (CPC) micelles does not prevent the studied imidazole derivatives reversible binding. The obtained materials can be used to develop effective receptors for recognition, delivery, and prolonged release of drug compounds to the sites of their functioning. Considering that cetylpyridinium chloride is a widely used cationic biocide as a disinfectant, the designed materials may also prove to be effective antimicrobial agents.

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“…Information related to the efficiency of fluorescence emission is important to explain the inactivation pathway related to PDT. 54 Figure 3 shows fluorescence emission for (1) and (2); both show photoluminescence at a visible range in the electromagnetic spectrum. As shown in Figure 3, fluorescence emission wavelength was located at 651 nm for both compounds, the energy transition did not change after the Sn (IV) ion insertion; however, fluorescence emission intensity was more high compound (1).…”

Section: Photophysical Properties Deamination Of փ Fmentioning

confidence: 99%

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

et al. 2021

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Background: Photodynamic therapy activity against different biological systems has been reported for porphyrins. Porphyrin modifications through peripheral groups and/or by metal insertion inside the ring are main alternatives for the improvement of its photo-physical properties. In this study, we synthesized and characterized 5,10,15,20-tetrakis(4-bromophenyl)porphyrin and the dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV). Methods: Metal-free porphyrin was synthesized using the Alder method, while the Sn(IV)-porphyrin complex was prepared by combining metal-free porphyrin with stannous chloride in DMF; the reaction yields were 47% and 64% respectively. Metal-free porphyrin was characterized by UV-Vis, FT-IR, ESI-mass spectrometry and 13C-NMR. Additionally, the Sn(IV) -porphyrin complex was characterized using UV-Vis and FT-IR. Cyclic voltammetry tests in four different solvents. The fluorescence quantum yield (Φf) was measured using fluorescein as a standard, the singlet oxygen quantum yield (ΦD) was estimated using the standard 5,10,15,20-(tetraphenyl)porphyrin (H2TPP) and the quencher of singlet oxygen 1,3-diphenylisobenzofuran (DPBF). Results: UV-Vis assay showed typical Q and Soret bands for porphyrin and its metallo-porphyrin complex. Compounds showed photoluminescence at the visible range of electromagnetic spectrum. The inclusion of the metal in the porphyrin core changed the Φf from 0.15 to 0.05 and the ΦD increased from 0.55 to 0.59. Finally, the effect of the compounds on the viability of L. panamensis was evaluated by means of the MTT test. The results showed that both compounds decreased the viability of the parasite; this inhibitory activity was greater under light irradiation; the porphyrin compound had IC50 of 16.5 μM and the Sn(IV)-porphyrin complex had IC50 of 19.2 μM. Conclusion: The compounds were synthesized efficiently, their characterization was carried out by different spectroscopy techniques and their own signals were evidenced for both structures, both compounds decreased the cell viability of L. panamensis.

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Medium viscosity effect on fluorescent properties of Sn(IV)-tetra(4-sulfonatophenyl)porphyrin complexes in buffer solutions

Cited by 23 publications

References 41 publications

New Polyporphyrin Arrays with Controlled Fluorescence Obtained by Diaxial Sn(IV)-Porphyrin Phenolates Chelation with Cu2+ Cation

New Polyporphyrin Arrays with Controlled Fluorescence Obtained by Diaxial Sn(IV)-Porphyrin Phenolates Chelation with Cu2+ Cation

Molecular Recognition of Imidazole Derivatives by Co(III)-Porphyrins in Phosphate Buffer (pH = 7.4) and Cetylpyridinium Chloride Containing Solutions

Photophysical study and in vitro approach against Leishmania panamensis of dicloro-5,10,15,20-tetrakis(4-bromophenyl)porphyrinato Sn(IV)

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