Article Dans Une Revue Journal of Photochemistry and Photobiology A: Chemistry Année : 2018

Evaluation of temoporfin affinity to β-cyclodextrins assuming self-aggregation

Résumé

The interaction between the potent photosensitizer meta-tetrakis(3-hydroxyphenyl)chlorin (temoporfin, mTHPC) and a series of β-cyclodextrins (β-CDs) was investigated using spectroscopic analysis and molecular dynamics simulations. The possibility of improving its poor aqueous solubility with β-CDs was estimated by measuring both equilibrium solubility and association constants. Parameters of binding isotherms revealed that mTHPC strongly interacts with β-CD derivatives, forming 1:2 inclusion complexes in aqueous solution. We demonstrated that apparent binding constants strongly depend on mTHPC concentration due to the porphyrin self-aggregation. The estimated “correct” binding constants demonstrated that completely methylated β-CD exhibits the highest affinity (K = 1.1 × 107 M−1) as compared to randomly methylated β-CD (K = 7.1 × 105 M−1) and 2-hydroxypropyl substituted β-CD (K = 1.7 × 105 M−1). In fine, our results indicate that TM-β-CD should be considered as a potent vector for mTHPC targeted delivery.

Fichier principal
Vignette du fichier
yakavets 2018.pdf (3.65 Mo) Télécharger le fichier

Dates et versions

hal-01861135 , version 1 (21-01-2022)

Licence

Identifiants

Citer

Ilya Yakavets, Henri-Pierre Lassalle, Igor Yankovsky, Francesca Ingrosso, A. Monari, et al.. Evaluation of temoporfin affinity to β-cyclodextrins assuming self-aggregation. Journal of Photochemistry and Photobiology A: Chemistry, 2018, 367, pp.13-21. ⟨10.1016/j.jphotochem.2018.07.046⟩. ⟨hal-01861135⟩
220 Consultations
195 Téléchargements

Altmetric

Partager

  • More