Advances in the Chemistry of Porphyrins and Related Macrocycles

Romeo, Andrea; Castriciano, Maria Angela; Scolaro, Luigi Monsù

doi:10.3390/ijms22147487

Cited by 1 publication

(1 citation statement)

References 12 publications

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“…Photodynamic therapy (PDT) has proved to be an efficient and safe treatment for many socially significant diseases, such as superficial malignancies of different etiology and localized antibiotic-resistant microbial infections [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. PDT is considered an alternative for, or the important part of, combined treatment, including traditional surgical intervention, chemo-or antibiotic therapy [2][3][4][5][6][7][8][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Solvation, Cancer Cell Photoinactivation and the Interaction of Chlorin Photosensitizers with a Potential Passive Carrier Non-Ionic Surfactant Tween 80

Кустов

Morshnev

Kukushkina

et al. 2022

IJMS

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Cancer and drug-resistant superinfections are common and serious problems afflicting millions worldwide. Photodynamic therapy (PDT) is a successful and clinically approved modality used for the management of many neoplastic and nonmalignant diseases. The combination of the light-activated molecules, so-called photosensitizers (PSs), with an appropriate carrier, is proved to enhance PDT efficacy both in vitro and in vivo. In this paper, we focus on the solvation of several potential chlorin PSs in the 1-octanol/phosphate saline buffer biphasic system, their interaction with non-ionic surfactant Tween 80 and photoinactivation of cancer cells. The chlorin conjugates containing d-galactose and l-arginine fragments are found to have a much stronger affinity towards a lipid-like environment compared to ionic chlorins and form molecular complexes with Tween 80 micelles in water with two modes of binding. The charged macrocyclic PSs are located in the periphery of surfactant micelles near hydrophilic head groups, whereas the d-galactose and l-arginine conjugates are deeper incorporated into the micelle structure occupying positions around the first carbon atoms of the hydrophobic surfactant residue. Our results indicate that both PSs have a pronounced affinity toward the lipid-like environment, leading to their preferential binding to low-density lipoproteins. This and the conjugation of chlorin e6 with the tumor-targeting molecules are found to enhance their accumulation in cancer cells and PDT efficacy.

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