Effective cell uptake of nanoassemblies of a fluorescent amphiphilic cyclodextrin and an anionic porphyrin

Mazzaglia, Antonino; Valerio, Antonio; Micali, Norberto; Villari, Valentina; Quaglia, Fabiana; Castriciano, Maria Angela; Scolaro, Luigi Monsù; Giuffrè, Maria; Siracusano, Gabriel; Sciortino, Maria Teresa

doi:10.1039/c1cc12821c

Cited by 29 publications

(33 citation statements)

References 24 publications

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“…Figure 4A presents the UV−vis spectra in PBS. As in other studies, 12 an excess of cyclodextrin was used as the complexing agent. Free (Bu 3 Sn) 4 TPPS exhibits a B-band centered at 414 nm, which is red-shifted at 420 nm, exhibiting hypochromicity in the (Bu 3 Sn) 4 TPPS/SC6OH complexes (at both the 1:5 and 1:10 molar ratios).…”

Section: ■ Resultsmentioning

confidence: 99%

Supramolecular Assemblies Based on Complexes of Nonionic Amphiphilic Cyclodextrins and a meso-Tetra(4-sulfonatophenyl)porphine Tributyltin(IV) Derivative: Potential Nanotherapeutics against Melanoma

et al. 2013

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Amphiphilic cyclodextrin (ACyD) provides water-soluble and adaptable nanovectors by modulating the balance between the hydrophobic and hydrophilic chains at both CyD sides. This work aimed to design nanoassemblies based on nonionic and hydrophilic ACyD (SC6OH) for the delivery of a poor-water-soluble organotin(IV)-porphyrin derivative [(Bu3Sn)4TPPS] to melanoma cancer cells. To characterize the porphyrin derivatives under simulated physiological conditions, a speciation was performed using complementary techniques. In aqueous solution (≤ 20 μM), (Bu3Sn)4TPPS primarily exists as a monomer (2 in Figure 1), as suggested by the low static anisotropy (ρ ≈ 0.02) with a negligible formation of porphyrin supramolecular aggregates. MALDI-TOF spectra indicate the presence of moieties (i.e., [(Bu3Sn)3TPPS](-)) that are derivatives of the monomeric species. Spectrofluorimetry coupled with potentiometric measurements primarily assesses the presence of the hydrolytic [(Bu3Sn)4TPPS (OH)4](4-) species under physiological conditions. Nanoassemblies of (Bu3Sn)4TPPS/SC6OH were prepared by dispersion of organic films in PBS at pH 7.4 and were investigated using a combination of spectroscopic and morphological techniques. The UV-vis and emission fluorescence spectra of the (Bu3Sn)4TPPS/SC6OH reveal shifts in the peculiar bands of the organotin(IV)-porphyrin derivative due to its interaction with the ACyD supramolecular assemblies in aqueous solution. The mean size was within the range of 100-120 nm. The ξ-potential was negative (-16 mV) for the (Bu3Sn)4TPPS/SC6OH nanoassemblies, with an entrapment efficiency of approximately 67%. The intracellular delivery, cytotoxicity, nuclear morphology and cell growth kinetics were evaluated via fluorescence microscopy on A375 human melanoma cells. The delivery of (Bu3Sn)4TPPS by ACyD with respect to free (Bu3Sn)4TPPS increases the internalization efficiency and cytotoxicity to induce apoptotic cell death and, at lower concentrations, changes the cellular morphology and prevents cell proliferation.

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Section: ■ Resultsmentioning

confidence: 99%

Supramolecular Assemblies Based on Complexes of Nonionic Amphiphilic Cyclodextrins and a meso-Tetra(4-sulfonatophenyl)porphine Tributyltin(IV) Derivative: Potential Nanotherapeutics against Melanoma

et al. 2013

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“…Over the past twenty years, amphiphilic cyclodextrins (aCD) formed with α-, β-, or γ-CD have given rise to a wide interest in the scientific community because of their versatility both as drug carriers [ 11 , 14 – 15 ] and as self-assembling systems for molecular recognition [ 16 – 18 ]. Different research groups investigated the aCD behaviour in solution, elucidating their nanostructures and physicochemical behaviour, including the temperature- and concentration-dependence of the supramolecular structures, or the pH dependence of water solubility, so as to improve our understanding of their activity as drug delivery systems [ 19 – 20 ] and of the biological fate of the assemblies [ 21 – 22 ]. The balance between the hydrophobic and the polar groups on the two CD rims modulates the formation of micelles, vesicles, nanospheres (or dense aggregates), and nanocapsules [ 1 ].…”

Section: Introductionmentioning

confidence: 99%

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

Raffaini¹,

Mazzaglia²

2015

Beilstein J. Org. Chem.

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SummaryAmphiphilically modified cyclodextrins may form various supramolecular aggregates. Here we report a theoretical study of the aggregation of a few amphiphilic cyclodextrins carrying hydrophobic thioalkyl groups and hydrophilic ethylene glycol moieties at opposite rims, focusing on the initial nucleation stage in an apolar solvent and in water. The study is based on atomistic molecular dynamics methods with a “bottom up” approach that can provide important information about the initial aggregates of few molecules. The focus is on the interaction pattern of amphiphilic cyclodextrin (aCD), which may interact by mutual inclusion of the substituent groups in the hydrophobic cavity of neighbouring molecules or by dispersion interactions at their lateral surface. We suggest that these aggregates can also form the nucleation stage of larger systems as well as the building blocks of micelles, vesicle, membranes, or generally nanoparticles thus opening new perspectives in the design of aggregates correlating their structures with the pharmaceutical properties.

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“…In 2011, the same team [ 165 ] used the above amphiphilic TPPS 4 /SC 6 -β-CD-NH 2 nanoassemblies covalently functionalized by the dansyl fluorophore. The resulting supramolecular system showed a good PS delivery while allowing a simultaneously detection of carrier and PS in tumor cells ( Figure 37 ).…”

Section: Cyclodextrins For Anticancer Photodynamic Therapymentioning

confidence: 99%

“…Finally, Mazzaglia et al in 2017 [ 168 ] described the elaboration of a novel nanophototherapeutic using the same emulsion–solvent evaporation procedure in a water environment as described in their previous studies [ 162 , 163 , 165 , 166 , 167 ]. For this novel nanoassembly (hydrodynamic size of around 40 nm) and as reported in their previous work [ 164 ], the authors used the same water-soluble anionic PS (TPPS 4 ), but this time with a new cationic amphiphilic CD, i.e., heptakis[6-(2-aminoethylthio)-6-deoxy-2,3-di- O -hexanoyl] cyclomaltoheptaose (CD-N) ( Figure 42 ).…”

Section: Cyclodextrins For Anticancer Photodynamic Therapymentioning

confidence: 99%

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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Effective cell uptake of nanoassemblies of a fluorescent amphiphilic cyclodextrin and an anionic porphyrin

Abstract: An emitting nanoassembly composed of a novel amphiphilic cyclodextrin functionalised with a covalently appended fluorophore and an anionic porphyrin internalizes effectively in tumor cells, allowing simultaneously the detection of carrier and photosensitiser.

Cited by 29 publications

References 24 publications

Supramolecular Assemblies Based on Complexes of Nonionic Amphiphilic Cyclodextrins and a meso-Tetra(4-sulfonatophenyl)porphine Tributyltin(IV) Derivative: Potential Nanotherapeutics against Melanoma

Supramolecular Assemblies Based on Complexes of Nonionic Amphiphilic Cyclodextrins and a meso-Tetra(4-sulfonatophenyl)porphine Tributyltin(IV) Derivative: Potential Nanotherapeutics against Melanoma

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

Use of Cyclodextrins in Anticancer Photodynamic Therapy Treatment

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