Adducts between Dansylated Poly(propylene amine) Dendrimers and Anthracene Clips Mediated by Zn<sup>II</sup> Ions: Highly Efficient Photoinduced Energy Transfer

Branchi, Barbara; Ceroni, Paola; Balzani, Vincenzo; Bergamini, Giacomo; Klärner, Frank‐Gerrit; Vögtle, Fritz

doi:10.1002/chem.200802300

Cited by 16 publications

(14 citation statements)

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“…The lipophilic (oleic acid) and hydrophilic [hexakis(ethylene glycol)] appendages were attached through ester linkages, chemically stable but easily cleavable in vivo by esterase-mediated degradation, in analogy with previously studied systems. [130][131][132][133][134][135][136] The synthesis of HoThyDansRu was accomplished in nine steps starting from uridine. In addition, dansyl-based probes are very sensitive to solvent polarity conditions, thus providing relevant information on their local environments.…”

Section: A Fluorescently Labelled Nucleolipid Ruthenium(iii) Complexmentioning

confidence: 99%

Ru^III Complexes for Anticancer Therapy: The Importance of Being Nucleolipidic

et al. 2016

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Ruthenium complexes are attracting increasing attention as second‐generation metal‐based anticancer agents, with NAMI‐A and KP1019 as the major representatives of this class having undergone clinical trials. Our recent interest has been focused on the synthesis and characterization of new amphiphilic derivatives of nucleosides (nucleolipids). These compounds have been selected as core scaffolds linked to RuIII complexes and capable of self‐assembly into stable nanostructures in aq. solutions so to transport the metal ions efficiently into the cell. Through the use of ribo‐ and deoxyribonucleosides as starting building blocks, a mini‐library of nucleolipidic RuIII complexes decorated with diverse hydrophilic and lipophilic chains and incorporating the NAMI‐A analogue AziRu has been prepared. When co‐aggregated with biocompatible lipids, these RuIII‐containing nucleolipids proved to be stable for months under physiological conditions. Detailed microstructural characterization, carried out by a combined approach including different physico‐chemical techniques, allowed their stability, size and shape to be determined. Tested on a panel of human and non‐human cells, all of the studied RuIII complexes showed potent in vitro anticancer activity, significantly higher than that of NAMI‐A‐like analogues, and minimal toxicity. Here we summarize the design and synthetic procedures developed to prepare these new Ru‐containing candidate drugs, discussing the beneficial effects achievable through exploiting nucleolipid appendages in the delivery of metal‐based drugs.

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Section: A Fluorescently Labelled Nucleolipid Ruthenium(iii) Complexmentioning

confidence: 99%

Ru^III Complexes for Anticancer Therapy: The Importance of Being Nucleolipidic

et al. 2016

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“…Dansyl fluorophore has found numerous applications in the design of optical sensors for neutral analytes (e.g. dansylappended cyclodextrins (12)(13)(14)(15)) as well as for metal ions on the basis of open-chain (16 -20) and macrocyclic chelators (21)(22)(23)(24)(25)(26), fluorescent peptides and proteins (27)(28)(29) and modified materials (film-coated glass (30), silica nano-particles (31,32), silicon nano-wires (33), dendrimers (34), microgels (35), etc.). In the late 1990s, first dansyl group-containing thiacalix [4]arene (36) and calix [4]arene (37) were reported as selective chemosensors of Cd 2þ and Hg 2þ , respectively.…”

Section: Introductionmentioning

confidence: 99%

Dansyl-containing fluorogenic calixarenes as optical chemosensors of hazardous metal ions: a mini-review

Talanova

Talanov

2010

Supramolecular Chemistry

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Fluorescent chemosensors serve as an efficient tool for selective detection of toxic metal ions (Hg 2þ , Cd 2þ , Pb 2þ , etc.) in the environment. This review is focused on optical metal ion recognition with employment of calixarene-based sensors containing one or more dansyl fluorophore groups. The effect of structural variations, including the mode of dansyl unit attachment, calixarene scaffold type and conformation, as well as the identity and pattern of upper-and lower-rim substituents on the selectivity and sensitivity of these fluoroionophores towards hazardous metal ions is discussed.

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“…[16] On account of the sulfate substituents attached to the bridging benzene unit (Scheme 1), C can play the role of ligand for metal ions, as previously reported for Zn 2 + . [17] Titration of a 1. www.chemeurj.org oxygen emission intensity at 1270 nm (empty circles in Figure 3). All the observed spectral changes reach a plateau at around 1 equiv of metal ion per clip, thereby suggesting the formation of a 1:1 complex between Nd 3 + and the clip.…”

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confidence: 99%

A Light‐Harvesting Antenna Resulting from the Self‐Assembly of Five Luminescent Components: A Dendrimer, Two Clips, and Two Lanthanide Ions

Branchi

Ceroni

Balzani

et al. 2010

Chemistry A European J

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We have investigated the self-assembly of three luminescent species in CH(3)CN/CH(2)Cl(2), namely: 1) a polylysin dendrimer (D) composed of 21 aliphatic amide units and 24 green luminescent dansyl chromophores at the periphery, 2) a molecular clip (C) with two blue luminescent anthracene sidewalls and a benzene bridging unit that bears two sulfate groups in the para position, and 3) a near infrared (NIR)-emitting Nd(3+) ion. For purposes of comparison, analogous systems have also been investigated in which Gd(3+) replaced Nd(3+). The dendrimer and the clip can bind Nd(3+) ions with formation of [D.2Nd(3+)] and [C.Nd(3+)] complexes, in which energy transfer from dansyl and, respectively, anthracene to Nd(3+) ion takes place with 65 and 8% efficiency, in air-equilibrated solution. In the case of [C.Nd(3+)], the energy-transfer efficiency is quenched by dioxygen, thereby showing that the energy donor is the lowest triplet excited state of anthracene. In [D.2Nd(3+)] the intrinsic emission efficiency of Nd(3+) is much higher (ca. 5 times) than in [C.Nd(3+)] because of a better protection of the excited lanthanide ion towards nonradiative deactivation caused by interaction with solvent molecules. By mixing solutions of D, Nd(3+), and C with proper concentrations, a supramolecular structure with five components of three different species, [D.2Nd(3+).2C], is formed. The excitation light absorbed by the clips is transferred with 100% efficiency to the dansyl units of the dendrimer and then to the Nd(3+) ions with 65% efficiency either in the presence or absence of dioxygen. These results show that the [D.2Nd(3+).2C] complex is able to efficiently harvest UV light by the 24 dansyl units of the dendrimer and the four anthracene chromophores of the two clips, and efficiently transfer it to the encapsulated Nd(3+) ions that emit in the NIR spectral region.

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Adducts between Dansylated Poly(propylene amine) Dendrimers and Anthracene Clips Mediated by Zn^II Ions: Highly Efficient Photoinduced Energy Transfer

Cited by 16 publications

References 68 publications

Ru^III Complexes for Anticancer Therapy: The Importance of Being Nucleolipidic

Ru^III Complexes for Anticancer Therapy: The Importance of Being Nucleolipidic

Dansyl-containing fluorogenic calixarenes as optical chemosensors of hazardous metal ions: a mini-review

A Light‐Harvesting Antenna Resulting from the Self‐Assembly of Five Luminescent Components: A Dendrimer, Two Clips, and Two Lanthanide Ions

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Adducts between Dansylated Poly(propylene amine) Dendrimers and Anthracene Clips Mediated by ZnII Ions: Highly Efficient Photoinduced Energy Transfer

Cited by 16 publications

References 68 publications

RuIII Complexes for Anticancer Therapy: The Importance of Being Nucleolipidic

RuIII Complexes for Anticancer Therapy: The Importance of Being Nucleolipidic

Dansyl-containing fluorogenic calixarenes as optical chemosensors of hazardous metal ions: a mini-review

A Light‐Harvesting Antenna Resulting from the Self‐Assembly of Five Luminescent Components: A Dendrimer, Two Clips, and Two Lanthanide Ions

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Adducts between Dansylated Poly(propylene amine) Dendrimers and Anthracene Clips Mediated by Zn^II Ions: Highly Efficient Photoinduced Energy Transfer

Ru^III Complexes for Anticancer Therapy: The Importance of Being Nucleolipidic

Ru^III Complexes for Anticancer Therapy: The Importance of Being Nucleolipidic