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Structural and physico-chemical determinants of the interactions of macrocyclic photosensitizers with cells

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Abstract

New therapies have been developed using reactive oxygen species produced by light-activation of photosensitizers (PS). Since the lifetime of these species is extremely short and their diffusion in space is limited, the photo-induced reactions primarily affect the cell organelles labeled by the PS. In addition to the development of molecules with the best optical and photosensitizing properties, considerable research has been done to understand the physico-chemical parameters governing their subcellular localization. In this review, we examine these parameters to establish the structure/efficacy relationships, which allow specific targeting of PS. We examine the effect of subcellular localization on the cellular response to photosensitization processes. We discuss the determinants of subcellular localization, including the hydrophobic/hydrophilic balance, the specific charge effects and the dynamics of PS’ transfer through membranes. Specific targeting can also be achieved with molecular structures able to recognize cellular or intracellular receptors, and this is also dealt with in this paper.

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Abbreviations

5-ALA:

5-Aminolevulinic acid

AlPcS n :

Sulfonated aluminum phthalocyanine

ATP:

Adenosine-5′-triphosphate

Bcl-2:

Antiapoptotic protein identified on B-cell lymphoma 2

Bid:

BH3 interacting domain death agonist

BPD:

Benzoporphyrin derivative

BPD-MA:

Benzoporphyrin derivative monoacid ring A

Ce6:

Chlorin e6

DP:

Deuteroporphyrin

HP:

Hematoporphyrin

HpD:

Hematoporphyrin derivative

LCP:

Lysyl chlorin p6

m-THPC:

Meso-tetrahydroxyphenylchlorin

PBR:

Benzodiazepine receptor

PCI:

Photochemical internalization

PDT:

Photodynamic therapy

Ppe:

Pyropheophorbide-a

PpIX:

Protoporphyrin IX

PS:

Photosensitizer

ROS:

Reactive oxygen species

SnET2:

Etiopurpurin

TPPS n :

Sulfonated tetraphenylporphyrin

ZnPc:

Zinc phthalocyanine

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  1. Laboratoire de Biophysique Moléculaire Cellulaire et Tissulaire (BIOMOCETI), CNRS UMR 7033, Université Pierre and Marie Curie, Genopole Campus 1, 5 rue Henri Desbruères, 91030, Evry Cedex, Paris, France

    Halina Mojzisova, Stéphanie Bonneau & Daniel Brault

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  1. Halina Mojzisova
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Correspondence to Halina Mojzisova.

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Mojzisova, H., Bonneau, S. & Brault, D. Structural and physico-chemical determinants of the interactions of macrocyclic photosensitizers with cells. Eur Biophys J 36, 943–953 (2007). https://doi.org/10.1007/s00249-007-0204-9

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  • Issue Date:

  • DOI: https://doi.org/10.1007/s00249-007-0204-9

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