Folic acid conjugates with photosensitizers for cancer targeting in photodynamic therapy: Synthesis and photophysical properties

Stallivieri, Aurélie; Colombeau, Ludovic; Jetpisbayeva, Gulim; Moussaron, Albert; Myrzakhmetov, Bauyrzhan; Arnoux, Philippe; Acherar, Samir; Vanderesse, Régis; Frochot, Céline

doi:10.1016/j.bmc.2016.10.004

Cited by 54 publications

(42 citation statements)

References 46 publications

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“…With several porphyrins and chlorins cojugated to FA the insertion of a short OEG did not significantly improve the hydrophilicity of the PS-FA conjugates [71]. However the hydrophilicity can be increased by introducing a high molecular weight PEG chain.…”

Section: Photosensitizers Conjugated To Small Moleculesmentioning

confidence: 90%

“…The conjugation of TPP to FA caused a slight decrease of the absorption coefficient that was also affected by the type of linker. However, a more recent study, showed that for several types of PS belonging to the porphyrin or chlorin families, the conjugation to folate through insertion of oligo(ethylene glycol) (OEG) did not affect negatively the PS photophysical properties [71]. The in vitro uptake of the two conjugates mentioned above was studied, using TPP as a reference.…”

Section: Photosensitizers Conjugated To Small Moleculesmentioning

confidence: 99%

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Strategies for optimizing the delivery to tumors of macrocyclic photosensitizers used in photodynamic therapy (PDT)

Moret

Reddi

2017

J. Porphyrins Phthalocyanines

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This review briefly summaries the principles and mechanisms of action of photodynamic therapy (PDT) as concerns its application in the oncological field, highlighting its drawbacks and some of the strategies that have been or are being explored to overcome them. The major aim is to increase the efficiency and selectivity of the photosensitizer (PS) uptake in the cancer cells for optimizing the PDT effects on tumors while sparing normal cells. Some attempts to achieve this are based on the conjugation of the PS to biomolecules (small ligands, peptides) functioning as carriers with the ability to efficiently penetrate cells and/or specifically recognize and bind proteins/receptors overexpressed on the surface of cancer cells. Alternatively, the PS can be entrapped in nanocarriers derived from various types of materials that can target the tumor by exploiting the enhanced permeability and retention (EPR) effects. The use of nanocarriers is particularly attractive because it allows the simultaneous delivery of more than one drug with the possibility of combining PDT with other therapeutic modalities.

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Section: Photosensitizers Conjugated To Small Moleculesmentioning

confidence: 90%

Section: Photosensitizers Conjugated To Small Moleculesmentioning

confidence: 99%

Strategies for optimizing the delivery to tumors of macrocyclic photosensitizers used in photodynamic therapy (PDT)

Moret

Reddi

2017

J. Porphyrins Phthalocyanines

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“…Furthermore, they can be easily modified, and their absorption in the red spectral region can be increased by conversion into chlorins andb acteriochlorins using reagents such as p-toluenesulfonylhydrazide. [12,14] Pyridyls ubstituents at meso-porphyrin positions are often used for quaternisation by N-alkylation to obtain water-soluble PSs, and it has been shown that at least two or more pyridyl units should be present to ensure water solubility upon quaternisation. [9] In our previouss tudy,w ep repared 5-(4-octadecanamidophenyl)-10,15,20-tris(N-methylpyridinium-3-yl)porphyrin trichloride (TMPyP3-C 17 H 35 )a nd ac omparison of this amphiphilic PS with the hydrophilic analogue 5-(4-acetamidophenyl)-10,15,20-tris(N-methylpyridinium-3-yl)porphyrin trichloride (TMPyP3-CH 3 )r evealed that the lipophilic moietys ignificantly improved PDT efficiency.…”

Section: Synthesis Characterisation and Photophysical Propertiesmentioning

confidence: 99%

“…Finally, the PS can be modified to improve passive targeting or to add active targeting, and thus to increase selectivity in PDT. For instance, this is the case for conjugates of porphyrin and chlorin, both synthetic and natural, with folic acid, which were used to target folate receptors over‐expressed on cancer cells …”

Section: Introductionmentioning

confidence: 99%

“…[11] Finally,t he PS can be modified to improve passive targeting or to add active targeting, andt hus to increaseselectivity in PDT.For instance, this is the case for conjugates of porphyrin and chlorin, both synthetic and natural, with folic acid, whichw ere used to targetf olate receptors over-expressedo ncancerc ells. [12] Recently,w ep repared an amphiphilic porphyrin with al ong alkyl chain as al ipophilic moiety, and three quaternised 3-pyridyl units that conferw ater solubility to the PS. [13] The PS showeds trongP DT activity on HeLa cells, but also as omewhat "dark toxicity", thusw ewere interested in preparing and investigating similarcompounds, withcertainvariations in the structure, to study the effects of these structurald ifferences on PDT efficiency on variousc ancerc ell lines, and to investigate other possible mechanismsinvolved in cell death.…”

Section: Introductionmentioning

confidence: 99%

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In Vitro Photodynamic Activity of N‐Methylated and N‐Oxidised Tripyridyl Porphyrins with Long Alkyl Chains and Their Inhibitory Activity in Sphingolipid Metabolism

et al. 2018

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A series of N-methylated and N-oxidised tripyridyl porphyrins were synthesised, characterised, and their PDT activity was studied with six cell lines. All the tested porphyrins with a long alkyl chain, except one, were more efficient for PDT than an N-methylated hydrophilic porphyrin and N-oxidised porphyrin without the long alkyl chain. Generally, N-methylated tripyridyl porphyrins were more active than those N-oxidised, but IC values for phototoxicity of two N-oxides, named TOPyP3-C H O and TOPyP3-C H , were still in the nanomolar concentration range for most of the tested cell lines. However, TOPyP3-C H did not show phototoxicity on human foreskin fibroblast cells. Two methylated amphiphilic porphyrins, named TMPyP3-C H and TMPyP4-C H showed significant dark toxicity, whereas none of the oxidopyridyl porphyrins were toxic without light activation. The selected photosensitisers were shown to be apoptosis inducers, and had inhibitory effects on the clonogenic growth of HCT116 and HeLa cells. All three N-methylated amphiphilic porphyrins significantly reduced the migratory potential of HCT116 cells. Porphyrins TMPyP3-C H and TOPyP3-C H reduced the activity of acid ceramidase, whereas TOPyP3-C H O had a significant inhibitory effect on sphingosine kinase 1 activity in HeLa cells. Compounds with this dual activity were shown to be the most promising photosensitisers, with potential to treat invasive cancers.

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Photosensitizers for Two‐Photon Excited Photodynamic Therapy

Sun

Zhang

et al. 2017

Adv Funct Materials

104

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Photodynamic therapy (PDT) is a noninvasive protocol for the treatment of various cancers and nonmalignant diseases. Light, oxygen, and photosensitizer (PS) are the essential three elements in a typical PDT process. Currently, there are two major barriers limiting the further development of PDT. One issue is limited tissue penetration, and the other is the lack of high-performance PSs. Therefore, the newly emerging two-photon excited PDT (2PE-PDT) has attracted considerable attention in recent years due to its advantages such as a higher spatial resolution and a greater penetration depth. In this review, focus is on (i) the principle of 2PE-PDT, (ii) the progression of PSs for 2PE-PDT, and (iii) the potential indications and future directions in this field.

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Folic acid conjugates with photosensitizers for cancer targeting in photodynamic therapy: Synthesis and photophysical properties

Cited by 54 publications

References 46 publications

Strategies for optimizing the delivery to tumors of macrocyclic photosensitizers used in photodynamic therapy (PDT)

Strategies for optimizing the delivery to tumors of macrocyclic photosensitizers used in photodynamic therapy (PDT)

In Vitro Photodynamic Activity of N‐Methylated and N‐Oxidised Tripyridyl Porphyrins with Long Alkyl Chains and Their Inhibitory Activity in Sphingolipid Metabolism

Photosensitizers for Two‐Photon Excited Photodynamic Therapy

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