Supramolecular sensitizer: complexation of meso-tetrakis(4-sulfonatophenyl)porphyrin with 2-hydroxypropyl-cyclodextrins

Mosinger, Jiří; Deumié, Michel; Lang, Kamil; Kubát, Pavel; Wagnerová, D. M.

doi:10.1016/s1010-6030(99)00204-x

Cited by 77 publications

(45 citation statements)

References 35 publications

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“…The mechanism responsible for triggering the conformational effects is also still under investigation as we so far lack direct evidence, however based on the results described here there seems to be a dual action initiated by TSPP. This porphyrin has been studied as a potential phototherapeutic drug [54] and has a large quantum yield of intersystem crossing to a triplet state [55]. Therefore, it was tempting to explain the photoinduced effects on the protein as a result of photosensitization of singlet oxygen followed by reactions with the backbone or the side chains of the amino acids in tubulin.…”

Section: Discussionmentioning

confidence: 99%

Photoinduced partial unfolding of tubulin bound to meso‐tetrakis(sulfonatophenyl) porphyrin leads to inhibition of microtubule formation in vitro

McMicken

Thomas

Brancaleon

2013

Journal of Biophotonics

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The irradiation of the complex formed by meso-tetrakis (sulfonatophenyl) porphyrin (TSPP) and tubulin was investigated as well as its effects on the structure and function of the protein. We have used tubulin as a model target to investigate whether photoactive ligands docked to the protein can affect the structure and function of the protein upon exposure to visible light. We observed that laser irradiation prompts bleaching of the porphyrin which is accompanied by a sharp decrease (∼2 ns) in the average fluorescence lifetime of the protein and a change in the dichroic spectrum consistent with a decrease of helical structure. The result indicated the photoinduced partial unfolding of tubulin. We also observed that such partial conformational change inhibits the formation of microtubules in vitro. We investigated whether photosensitization of reactive oxygen species was responsible for these effects. Even upon removal of O2 the protein still undergoes conformational changes indicating that irradiation of the bound porphyrin does not require the presence of O2 to prompt conformational and functional effects opening the possibility that other mechanisms (e.g., charge transfer) are responsible for the photoinduced mechanism.

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Section: Discussionmentioning

confidence: 99%

Photoinduced partial unfolding of tubulin bound to meso‐tetrakis(sulfonatophenyl) porphyrin leads to inhibition of microtubule formation in vitro

McMicken

Thomas

Brancaleon

2013

Journal of Biophotonics

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“…Among the possible β-CD-TPPS4 stoichiometries, those with 2:1 CD:TPPS4 stoichiometry in which two opposite phenyl moieties of the porphyrin ring are included into the CD cavity through its wider end have been reported to be the most stable. 53 The addition of other CDs with various pore sizes (i.e., α-CD, γ-CD, and TMe-β-CD) did not appreciably change the complexation rates of the tested metal ions relative to that in their absence. In the absence of Pb(II), inclusion complexes between CD and TPPS4 were observed in the spectrophotometric profiles Values obtained from correlation equations described in text.…”

Section: Spectroscopic Behavior and Impact Of CD Pore Sizementioning

confidence: 89%

β-Cyclodextrin as a Metal-anionic Porphyrin Complexation Accelerator in Aqueous Media

et al. 2016

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“…TPPS has capable to initiate a photochemical reaction by absorbing photons upon exposition to light at visible wavelength. Excited singlet oxygen is one of photochemical reaction product which is very aggressive and toxic for cellular tissues and will oxidize malignant cells [5]. Although the exact mechanism for photodynamic therapy of porphyrins in abnormal tissues is still not well known, numerous studies have confirmed its efficacy to be depend on the environmental characteristics and physicochemical properties of photosensitizer [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Solvent effect on protonation of tpps in water-DMF mixtures

Farajtabar¹,

Faeli²

2017

Bull. Chem. Soc. Eth.

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ABSTRACT. The protonation of 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin was investigated in aqueous solutions of N,N-dimethyformamide at 25 C and 0.1 mol.dm -3 sodium perchlorate. The solvent effect on value of protonation constant was examined by using the linear solvation energy relationship concept. The value of logK1, logK2 and logKt was correlated with the macroscopic (dielectric constant) and microscopic Kamlet-Taft parameters (,  and *) of binary mixtures. The solvent effects were analyzed in the terms of Kamlet, Abboud and Taft model (KAT). Multiple linear regression were used to find the contribution of the microscopic parameters containing  (hydrogen-bond acidity), * (dipolarity/polarizability) and  (hydrogen-bond basicity). It was found that  and  were the most predominant descriptors. Also, relationship with reciprocal of dielectric constant was obtained based on Born's model, showing the significance of specific solute-solvent interactions. Therefore the hydrogen bonding interactions between solute and solvent components are mainly responsible for the change in protonation constants of 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin in water-N,N-dimethyformamid binary mixtures.

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Supramolecular sensitizer: complexation of meso-tetrakis(4-sulfonatophenyl)porphyrin with 2-hydroxypropyl-cyclodextrins

Cited by 77 publications

References 35 publications

Photoinduced partial unfolding of tubulin bound to meso‐tetrakis(sulfonatophenyl) porphyrin leads to inhibition of microtubule formation in vitro

Photoinduced partial unfolding of tubulin bound to meso‐tetrakis(sulfonatophenyl) porphyrin leads to inhibition of microtubule formation in vitro

β-Cyclodextrin as a Metal-anionic Porphyrin Complexation Accelerator in Aqueous Media

Solvent effect on protonation of tpps in water-DMF mixtures

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