Spectral, electrochemical and docking studies of 5-indanol:β-CD inclusion complex

Sivakumar, K.; Hemalatha, G.; Parameswari, M.; Stalin, T.

doi:10.1080/00319104.2012.760085

“…The changes in the position and intensity of the band are assumed to results from changes in the solid microenvironment upon inclusion of TsIm into the CD cavity. The red shift in the absorbance maximum (bathochrome effect) was presumably caused by the imidazole ring being complexed in the hydrophobic interior of the CD cavity as already shown for other aromatic guests . Knowing that the thermodynamic activity of pure substances in the solid phase is normally taken as unity, the stoichiometry of the CD/TsIm complexes could be determined by DR UV–vis spectroscopy through a method of continuous variation (Job’s plot).…”

Section: Resultsmentioning

confidence: 95%

“…The red shift in the absorbance maximum (bathochrome effect) was presumably caused by the imidazole ring being complexed in the hydrophobic interior of the CD cavity as already shown for other aromatic guests. 72 Knowing that the thermodynamic activity of pure substances in the solid phase is normally taken as unity, the stoichiometry of the CD/TsIm complexes could be determined by DR UV−vis spectroscopy through a method of continuous variation (Job's plot). As an example, the Job's plot of the α-CD/TsIm couple is given in Figure 6.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Selective Secondary Face Modification of Cyclodextrins by Mechanosynthesis

Menuel

¹

,

Doumert

²

,

Saitzek

³

et al. 2015

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α-, β-, and γ-cyclodextrins (CDs) were modified on their secondary face by mechanosynthesis at room temperature using a laboratory-scale ball-mill. Mono-2-tosylated α-, β-, and γ-CDs were obtained in good yield from mixtures of native α-, β-, and γ-CDs, respectively, N-tosylimidazole, and an inorganic base, with each of them being in the solid state. The yields appeared to be dependent upon the nature of the base and the reaction time. A kinetic monitoring by (1)H NMR spectroscopy demonstrated that the highest yields in mono-2-tosyl-CDs were measured using KOH as a base in very short reaction times (up to 65% in 80 s). Mono-(2,3-manno-epoxide) α-, β-, and γ-CDs were subsequently synthesized by ball-milling a mixture of monotosylated α-, β-, and γ-CDs, respectively, and KOH. The characterization of the modified CDs was carried out by X-ray diffraction, mass spectrometry, solid-state NMR, and diffuse reflectance UV-vis (DR UV-vis) spectroscopies. Clues to the supramolecular arrangement of the molecules in the solid state provide information on the reaction mechanism.

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“…Finally, the potentials described in Table 2 corresponding to the redox process of ( 2 ) are in agreement with other reports for processes based on rings in porphyrin complexes. 72 , 73 …”

Section: Resultsmentioning

confidence: 99%

“…Finally, the potentials described in Table 2 corresponding to the redox process of (2) are in agreement with other reports for processes based on rings in porphyrin complexes. 72,73 Biological assay A wide variety of molecules have been evaluated as possible therapy against Leishmania spp in recent years: (i) aluminum and zinc phthalocyanines (ii) methylene blue, 5-aminolevulinic acid and porphyrin. The field of research on new substances with challenging properties in medicine and pharmacology is an important topic, which has become more relevant due to the appearance of resistant and emerging microorganisms.…”

Section: Electrochemical Characterizationmentioning

confidence: 99%

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

Espitia-Almeida

¹

,

Díaz‐Uribe

²

,

Vallejo

³

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.

show abstract

“…Finally, the potentials described in Table 2 corresponding to the redox process of (2) are in agreement with other reports for processes based on rings in porphyrin complexes. 72,73 Biological assay A wide variety of molecules have been evaluated as possible therapy against Leishmania spp in recent years: (i) aluminum and zinc phthalocyanines (ii) methylene blue, 5-aminolevulinic acid and porphyrin. The field of research on new substances with challenging properties in medicine and pharmacology is an important topic, which has become more relevant due to the appearance of resistant and emerging microorganisms.…”

Section: Electrochemical Characterizationmentioning

confidence: 99%

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

Espitia-Almeida

¹

,

Díaz‐Uribe

²

,

Vallejo

³

et al. 2021

F1000Res

0

View full text Add to dashboard Cite

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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Spectral, electrochemical and docking studies of 5-indanol:β-CD inclusion complex

Cited by 8 publications

References 37 publications

Selective Secondary Face Modification of Cyclodextrins by Mechanosynthesis

Selective Secondary Face Modification of Cyclodextrins by Mechanosynthesis

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

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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