Inclusion complexation with β-cyclodextrin derivatives alters photodynamic activity and biodistribution of meta-tetra(hydroxyphenyl)chlorin

Yankovsky, Igor; Bastien, Estelle; Yakavets, Ilya; Khludeyev, I. I.; Lassalle, Henri-Pierre; Gräfe, Susanna; Bezdetnaya, Lina; Zorin, Vladimir

doi:10.1016/j.ejps.2016.06.012

Cited by 34 publications

(30 citation statements)

References 38 publications

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“…Various CD–PS systems have been developed and can be formed by three types of binding mode of PSs with CDs, which are non-covalent binding (CD–PS inclusion complexes), covalent binding (CD–PS conjugates), and non-specific external binding (CD–PS nanoassemblies). For porphyrinoid PSs, it was found that CD–PS inclusion complexes can: (1) improve PDT efficiency [ 120 , 121 , 126 ] compared with free PSs; (2) reduce some drawbacks of PSs such as their lack of water solubility [ 120 , 121 , 124 , 125 , 126 ] and self-aggregation [ 124 , 127 ]; (3) induce a lower cytotoxicity than free PSs in some cases [ 120 ]; (4) lead to a better or different cellular uptake [ 125 , 129 ] even in spheroids [ 128 ]; (5) modify the intracellular distribution [ 127 ]; and (6) induce an acceleration of the PS diffusion into the biological media [ 127 ]. Similar results are also obtained for non-porphyrinoid PSs.…”

Section: Discussionmentioning

confidence: 99%

“…Recently, Yankovsky et al [ 127 ] studied the effect of two β-CDs derivatives, i.e., methyl-β-cyclodextrin (Me-β-CD) and HP-β-CD, at a wide range of concentrations on the in vitro and in vivo distribution of meta-tetra(hydroxyphenyl)chlorin (mTHPC). The authors found that the association of mTHPC with the β-CDs prevents its aggregation after introduction into blood, and enhanced its diffusion movement between biological structures.…”

Section: Cyclodextrins For Anticancer Photodynamic Therapymentioning

confidence: 99%

“…Results are expressed as the mean of three to four measurements with the vertical bar showing SD. Adapted from Yankovsky; Bastien; Yakavets; Khludeyev; Lassalle; Gräfe; Bezdetnaya; Zorin [ 127 ].…”

Section: Figurementioning

confidence: 99%

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Use of Cyclodextrins in Anticancer Photodynamic Therapy Treatment

et al. 2018

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Photodynamic therapy (PDT) is mainly used to destroy cancerous cells; it combines the action of three components: a photoactivatable molecule or photosensitizer (PS), the light of an appropriate wavelength, and naturally occurring molecular oxygen. After light excitation of the PS, the excited PS then reacts with molecular oxygen to produce reactive oxygen species (ROS), leading to cellular damage. One of the drawbacks of PSs is their lack of solubility in water and body tissue fluids, thereby causing low bioavailability, drug-delivery efficiency, therapeutic efficacy, and ROS production. To improve the water-solubility and/or drug delivery of PSs, using cyclodextrins (CDs) is an interesting strategy. This review describes the in vitro or/and in vivo use of natural and derived CDs to improve antitumoral PDT efficiency in aqueous media. To achieve these goals, three types of binding modes of PSs with CDs are developed: non-covalent CD–PS inclusion complexes, covalent CD–PS conjugates, and CD–PS nanoassemblies. This review is divided into three parts: (1) non-covalent CD-PS inclusion complexes, covalent CD–PS conjugates, and CD–PS nanoassemblies, (2) incorporating CD–PS systems into hybrid nanoparticles (NPs) using up-converting or other types of NPs, and (3) CDs with fullerenes as PSs.

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Section: Discussionmentioning

confidence: 99%

Section: Cyclodextrins For Anticancer Photodynamic Therapymentioning

confidence: 99%

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Use of Cyclodextrins in Anticancer Photodynamic Therapy Treatment

et al. 2018

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“…The commercial medicinal product that is based on mTHPC (Foscan ® ) requires low light doses and concentrations to be photoactive and has already been approved by the European Medicines Agency (EMA) for the palliative treatment of advanced head and neck squamous cell carcinoma since 2001 [ 6 , 7 ]. Recently, we demonstrated a unique possibility to alter the biodistribution of mTHPC using β-cyclodextrin (β-CD) derivatives ( Scheme 1 b) [ 8 , 9 ]. The binding constants of mTHPC with β-CD derivatives vary from 10 5 to 10 7 M −1 [ 10 ], providing the unique “nanoshuttle” transportation mechanism of mTHPC in biological media.…”

Section: Introductionmentioning

confidence: 99%

“…Depending on the concentration of β-CD derivatives, they could either accelerate mTHPC distribution from serum proteins to tumor targets increasing cellular uptake and providing a deeper mTHPC penetration in three-dimensional (3D) tumor models or “isolate” drug molecules hampering PS delivery [ 9 ]. Such remarkable results in vitro strongly depend on the local concentration of β-CD, and as such, in vivo application of β-CD formulations is complicated due to the quick β-CD removal from the circulating system after intravenous injection [ 8 ]. The control release of inclusion complexes in target tissue may be better achieved in the case of hybrid drug-in-cyclodextrin-in-liposome (DCL) formulation ( Scheme 1 c).…”

Section: Introductionmentioning

confidence: 99%

Temoporfin-in-Cyclodextrin-in-Liposome—A New Approach for Anticancer Drug Delivery: The Optimization of Composition

et al. 2018

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The main goal of this study was to use hybrid delivery system for effective transportation of temoporfin (meta-tetrakis(3-hydroxyphenyl)chlorin, mTHPC) to target tissue. We suggested to couple two independent delivery systems (liposomes and inclusion complexes) to achieve drug-in-cyclodextrin-in-liposome (DCL) nanoconstructs. We further optimized the composition of DCLs, aiming to alter in a more favorable way a distribution of temoporfin in tumor tissue. We have prepared DCLs with different compositions varying the concentration of mTHPC and the type of β-cyclodextrin (β-CD) derivatives (Hydroxypropyl-, Methyl- and Trimethyl-β-CD). DCLs were prepared by thin-hydration technique and mTHPC/β-CD complexes were added at hydration step. The size was about 135 nm with the surface charge of (−38 mV). We have demonstrated that DCLs are stable and almost all mTHPC is bound to β-CDs in the inner aqueous liposome core. Among all tested DCLs, trimethyl-β-CD-based DCL demonstrated a homogenous accumulation of mTHPC across tumor spheroid volume, thus supposing optimal mTHPC distribution.

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