β-Cyclodextrin-linked Ru complexes for oxidations and reductions

Woggon, Wolf‐D.; Schlatter, Alain; Wang, Hao

doi:10.1016/s0898-8838(08)00002-0

Cited by 9 publications

(4 citation statements)

References 36 publications

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“…Many functional groups or substituents have been covalently grafted onto the CD primary and/or secondary face, and the scope of applications has then been broadened to an impressive extent. For example, substituted CDs found application in catalysis, − enzyme mimics, , and materials , or drug delivery systems, , to name only a few possible uses.…”

Section: Introductionmentioning

confidence: 99%

Selective Secondary Face Modification of Cyclodextrins by Mechanosynthesis

et al. 2015

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α-, β-, and γ-cyclodextrins (CDs) were modified on their secondary face by mechanosynthesis at room temperature using a laboratory-scale ball-mill. Mono-2-tosylated α-, β-, and γ-CDs were obtained in good yield from mixtures of native α-, β-, and γ-CDs, respectively, N-tosylimidazole, and an inorganic base, with each of them being in the solid state. The yields appeared to be dependent upon the nature of the base and the reaction time. A kinetic monitoring by (1)H NMR spectroscopy demonstrated that the highest yields in mono-2-tosyl-CDs were measured using KOH as a base in very short reaction times (up to 65% in 80 s). Mono-(2,3-manno-epoxide) α-, β-, and γ-CDs were subsequently synthesized by ball-milling a mixture of monotosylated α-, β-, and γ-CDs, respectively, and KOH. The characterization of the modified CDs was carried out by X-ray diffraction, mass spectrometry, solid-state NMR, and diffuse reflectance UV-vis (DR UV-vis) spectroscopies. Clues to the supramolecular arrangement of the molecules in the solid state provide information on the reaction mechanism.

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Section: Introductionmentioning

confidence: 99%

Selective Secondary Face Modification of Cyclodextrins by Mechanosynthesis

et al. 2015

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“…To enhance the aqueous solubility of porphyrins, cyclodextrin–porphyrin conjugates have been prepared, either as enzyme mimics or as PSs and only in few examples as drug delivery systems . Whereas multisubstituted CD–porphyrin conjugates are reportedly water soluble, mono‐CD‐porphyrin conjugates display limited aqueous solubility .…”

Section: Introductionmentioning

confidence: 99%

Protoporphyrin IX–β‐Cyclodextrin Bimodal Conjugate: Nanosized Drug Transporter and Potent Phototoxin

Aggelidou

Theodossiou

Yannakopoulou

2013

Photochem & Photobiology

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Topical or systemic administration of 5-aminolevulinic acid (ALA) and its esters results in increased production and accumulation of protoporphyrin IX (PpIX) in cancerous lesions allowing effective application of photodynamic therapy (PDT). The large concentrations of exogenous ALA practically required to bypass the negative feedback control exerted by heme on enzymatic ALA synthesis and the strong dimerization propensity of ALA are shortcomings of the otherwise attractive PpIX biosynthesis. To circumvent these limitations and possibly enhance the phototoxicity of PpIX by adjuvant chemotherapy, covalent bonding of PpIX with a drug carrier, β-cyclodextrin (βCD) was implemented. The resulting PpIX + βCD product had both carboxylic termini of PpIX connected to the CD. PpIX + βCD was water soluble, was found to preferentially localize in mitochondria rather than in lysosomes both in MCF7 and DU145 cell lines while its phototoxiciy was comparable to that of PpIX. Moreover, PpIX + βCD effectively solubilized the breast cancer drug tamoxifen metabolite N-desmethyltamoxifen (NDMTAM) in water. The PpIX + βCD/NDMTAM complex was readily internalized by both cell lines employed. Furthermore, the multimodal action of PpIX + βCD was demonstrated in MCF7 cells: while it retains the phototoxic profile of PpIX and its fluorescence for imaging purposes, PpIX + βCD can efficiently transport tamoxifen citrate intracellularly and confer cell death through a synergy of photo- and chemotoxicity.

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“…A related system is the Zn(II)-TPP−βCD conjugate 4 designed by molecular modeling that mimics β-carotene-15,15′-monooxygenase, which oxidizes only the central (out of nine) E -conjugated double bond in β-carotene. The conjugate forms a supramolecular complex ( K = 8.3 × 10 6 M –1 ) with β-carotene by enclosure of its two cyclohexenyl end groups in the two βCD cavities with the polyene chain spanning the entire length of the porphyrin and the central double bond positioned close to the Zn(II) ion.…”

Section: Synthetic Porphyrinoid–cyclodextrin Biomimetic Systemsmentioning

confidence: 99%

Porphyrinoid–Cyclodextrin Assemblies in Biomedical Research: An Update

Mavridis

Yannakopoulou

2019

J. Med. Chem.

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Porphyrinoids, well-known cofactors in fundamental processes of life, have stimulated interest as synthetic models of natural systems and integral components of photodynamic therapy, but their utilization is compromised by self-aggregation in aqueous media. The capacity of cyclodextrins to include hydrophobic molecules in their cavity provides porphyrinoids with a protective environment against oxidation and the ability to disperse efficiently in biological fluids. Moreover, engineered cyclodextrin−porphyrinoid assemblies enhance the photodynamic abilities of porphyrinoids, can carry chemotherapeutics for synergistic modalities, and can be enriched with functions including cell recognition, tissue penetration, and imaging. This Perspective includes synthetic porphyrinoid−cyclodextrin models of proteins participating in fundamental processes, such as enzymatic catalysis, respiration, and electron transfer. In addition, since porphyrinoid− cyclodextrin systems comprise third generation photosensitizers, recent developments for their utilization in photomedicine, that is, multimodal therapy for cancer (e.g., PDT, PTT) and antimicrobial treatment, and eventually in biocompatible therapeutic or diagnostic platforms for next-generation nanomedicine and theranostics are discussed. Perspective pubs.acs.org/jmc

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β-Cyclodextrin-linked Ru complexes for oxidations and reductions

Cited by 9 publications

References 36 publications

Selective Secondary Face Modification of Cyclodextrins by Mechanosynthesis

Selective Secondary Face Modification of Cyclodextrins by Mechanosynthesis

Protoporphyrin IX–β‐Cyclodextrin Bimodal Conjugate: Nanosized Drug Transporter and Potent Phototoxin

Porphyrinoid–Cyclodextrin Assemblies in Biomedical Research: An Update

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