Porphyrin−Cyclodextrin Conjugates as a Nanosystem for Versatile Drug Delivery and Multimodal Cancer Therapy

Králová, Jarmila; Kejík, Zdeněk; Břı́za, Tomáš; Poučková, P; Král, Aleš; Martásek, Pavel; Král, Vladimír

doi:10.1021/jm9007278

Cited by 116 publications

(37 citation statements)

References 44 publications

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“…They also conducted binding studies of several chemotherapy drugs with cyclodextrin (CD) for versatile drug delivery and in vitro and in vivo studies. 82 Binding studies revealed that doxorubicin has good binding affinity towards Por–γ-CD 3 and paclitaxel has good binding affinity towards Por–β-CD conju-gates 1, 2 and 4. Supramolecular carrier–chemotherapy drug complexes were then tested in vitro using 4T1 and human chronic myelogenous leukemia K562 cell lines, and in vivo using BALB/c mice transplanted with 4T1 cells.…”

Section: Substituted Fluorinated Porphyrinoids For Biological Applicamentioning

confidence: 98%

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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Porphyrinoids are robust heterocyclic dyes studied extensively for their applications in medicine and as photonic materials because of their tunable photophysical properties, diverse means of modifying the periphery, and the ability to chelate most transition metals. Commercial applications include their use as phthalocyanine dyes in optical discs, porphyrins in photodynamic therapy, and as oxygen sensors. Most applications of these dyes require exocyclic moieties to improve solubility, target diseases, modulate photophysical properties, or direct the self-organization into architectures with desired photonic properties. The synthesis of the porphyrinoid depends on the desired application, but the de novo synthesis often involves several steps, is time consuming, and results in low isolated yields. Thus, the application of core porphyrinoid platforms that can be rapidly and efficiently modified to evaluate new molecular architectures allows researchers to focus on the design concepts rather than the synthesis methods, and opens porphyrinoid chemistry to a broader scientific community. We have focused on several widely available, commercially viable porphyrinoids as platforms: meso-perfluorophenylporphyrin, perfluoro-phthalocyanine, and meso-perfluorophenylcorrole. The perfluorophenylporphyrin is readily converted to the chlorin, bacteriochlorin, and isobacteriochlorin. Derivatives of all six of these core platforms can be efficiently and controllably made via mild nucleophilic aromatic substitution reactions using primary S, N, and O nucleophiles bearing a wide variety of functional groups. The remaining fluoro groups enhance the photo and oxidative stability of the dyes and can serve as spectroscopic signatures to characterize the compounds or in imaging applications using 19F NMR. This review provides an overview of the chemistry of fluorinated porphyrinoids that are being used as a platform to create libraries of photo-active compounds for applications in medicine and materials.

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Section: Substituted Fluorinated Porphyrinoids For Biological Applicamentioning

confidence: 98%

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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“…This supramolecular nanoassembly simultaneously releases cytotoxic 1 O 2 and nitric oxide under illumination with visible light, resulting in amplified cancer-cell mortality [9]. By attaching porphyrin to γ-CD and dimeric β-CD, which are both able to form inclusion complexes with cytotoxic drug molecules such as doxorubicin and paclitaxel, nanocarriers with multimodal therapeutic effects (PDT and chemotherapy) have been developed by Král et al [10–11]. The results achieved by these groups clearly demonstrated the numerous advantages of the PS–CD coupling.…”

Section: Introductionmentioning

confidence: 99%

Novel β-cyclodextrin–eosin conjugates

Benkovics

Afonso

Darcsi

et al. 2017

Beilstein J. Org. Chem.

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Eosin B (EoB) and eosin Y (EoY), two xanthene dye derivatives with photosensitizing ability were prepared in high purity through an improved synthetic route. The dyes were grafted to a 6-monoamino-β-cyclodextrin scaffold under mild reaction conditions through a stable amide linkage using the coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride. The molecular conjugates, well soluble in aqueous medium, were extensively characterized by 1D and 2D NMR spectroscopy and mass spectrometry. Preliminary spectroscopic investigations showed that the β-cyclodextrin–EoY conjugate retains both the fluorescence properties and the capability to photogenerate singlet oxygen of the unbound chromophore. In contrast, the corresponding β-cyclodextrin–EoB conjugate did not show either relevant emission or photosensitizing activity probably due to aggregation in aqueous medium, which precludes any response to light excitation.

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“…In 2010, the same team synthesized a new Lego-like system composed of perfluorinated porphyrin–CD conjugates (P(CD) x ) and various chemotherapy drugs [ 140 ]. The perfluorinated porphyrins were first conjugated to CDs (β-CD or γ-CD) by covalent ether bond ( Figure 20 ) using the same strategy as described in their previous study [ 139 ].…”

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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Porphyrin−Cyclodextrin Conjugates as a Nanosystem for Versatile Drug Delivery and Multimodal Cancer Therapy

Cited by 116 publications

References 44 publications

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Novel β-cyclodextrin–eosin conjugates

Use of Cyclodextrins in Anticancer Photodynamic Therapy Treatment

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