Novel nucleotide–calixarene conjugates via phosphoester linkage

Consoli, Grazia Maria Letizia; Granata, Giuseppe; Galante, Eva; Cunsolo, Francesca; Geraci, Corrada

doi:10.1016/j.tetlet.2006.03.043

Cited by 14 publications

(3 citation statements)

References 21 publications

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“…Indeed, this group was successfully employed in the conjugation of calixarene and nucleoside derivatives. 26 However, the phosphoramidite chemistry required in the coupling stage is delicate and involves numerous steps compared to other strategies envisaged (see below), that is not consistent with our goal. Furthermore, the hydrolytic reactivity of nucleoside-based phosphodiesters could be less pronounced in alkaline medium than for carboxylic or carbonate esters.…”

Section: Synthesismentioning

confidence: 87%

“…25 More recently, Consoli et al reported the synthesis of several calixarene-nucleoside conjugates, comprising 2 0 -deoxy-thymidine, -adenosine, -cytosine and -guanosine nucleosides, grafted via phosphodiester linkers on the lower rim of the tetra-p-tert-butylcalix [4]arene. 26 The authors described the self-assembling behavior of these derivatives in chloroform 27 and water, 28 as well as a preliminary investigation dedicated to their capability to inhibit in vitro DNA replication during PCR amplification. 29 Most of these contributions deal with natural nucleosides, with the aim of generating self-assembled nanostructures or a biological activity by means of pre-organization of nucleoside subunits.…”

Section: Introductionmentioning

confidence: 99%

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New potential prodrugs of aciclovir using calix[4]arene as a lipophilic carrier: synthesis and drug-release studies at the air–water interface

et al. 2012

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Two tetra-p-tert-butyl-calix [4]arene species bearing one or two anti-HSV aciclovir units tethered via carbodiester linkages at the lower rim were synthesized as possible antiviral prodrugs. The amphiphilic properties of these derivatives were studied using Langmuir balance at the air-water and air-carbonate buffer interfaces; the monolayers formed were stable on both subphases. Monolayers formed with these molecules on a carbonate buffer subphase at pH 10 and 37 1C were then used for monitoring hydrolysis of the diester linkage. The release of free aciclovir of around 30% in 3 days was observed with both derivatives, as shown with HPLC.

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Section: Synthesismentioning

confidence: 87%

Section: Introductionmentioning

confidence: 99%

New potential prodrugs of aciclovir using calix[4]arene as a lipophilic carrier: synthesis and drug-release studies at the air–water interface

et al. 2012

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“…Calix[ n ]arenes are a family of polyphenolic macrocycles, characterized by relevant synthetic versatility and the presence of a hydrophobic cavity with remarkable hosting properties . The calixarene skeleton can be variously functionalized at both the upper and lower rim to give a variety of derivatives , with a large range of applications in different areas including pharmacology . Rudkevich and Neri investigated the use of calix[4]arene derivatives as cages for storage and release of gaseous NO. , Recently, we have reported the first example of a calixarene-based system delivering NO on demand .…”

mentioning

confidence: 99%

Design, Synthesis, and Antibacterial Activity of a Multivalent Polycationic Calix[4]arene–NO Photodonor Conjugate

Consoli¹,

Bari

Blanco³

et al. 2017

ACS Med. Chem. Lett.

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The role of nitric oxide (NO) as an antimicrobial and anticancer agent continues to stimulate the search of compounds generating NO in a controlled fashion. Photochemical generators of NO are particularly appealing due to the accurate spatiotemporal control that light-triggering offers. This contribution reports a novel molecular construct in which multiple units of 3-(trifluoromethyl)-4-nitrobenzenamine NO photodonor are clustered and spatially organized by covalent linkage to a calix[4]arene scaffold bearing two quaternary ammonium groups at the lower rim. This multivalent calix[4]arene-NO donor conjugate is soluble in hydro-alcoholic solvent where it forms nanoaggregates able to release NO under the exclusive control of visible light inputs. The light-stimulated antibacterial activity of the nanoconstruct is demonstrated by the effective bacterial load reduction of Gram-positive ATCC 6538 and Gram-negative ATCC 10536.

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Template‐Assembled Synthetic G‐Quartets (TASQs)

Nikan

Sherman

2008

Angewandte Chemie

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Ein ungewöhnliches Quartett: Das Anheften von vier Guaninresten an einen Cavitanden lieferte eine Verbindung, die in CDCl3 templatvermittelt eine lipophile synthetische G‐Quartett(TASQ)‐Struktur ergab. Die Struktur ist im kationenfreien Zustand ungewöhnlich stabil. Dieser kationenfreie Korb sowie mögliche analoge kationengebundene Quartette und kationeninduzierte Quadruplexe könnten therapeutisch nützlich sein.

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Novel nucleotide–calixarene conjugates via phosphoester linkage

Cited by 14 publications

References 21 publications

New potential prodrugs of aciclovir using calix[4]arene as a lipophilic carrier: synthesis and drug-release studies at the air–water interface

New potential prodrugs of aciclovir using calix[4]arene as a lipophilic carrier: synthesis and drug-release studies at the air–water interface

Design, Synthesis, and Antibacterial Activity of a Multivalent Polycationic Calix[4]arene–NO Photodonor Conjugate

Template‐Assembled Synthetic G‐Quartets (TASQs)

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