Cyclic PNA hexamer-based compound: modelling, synthesis and inhibition of the HIV-1 RNA dimerization process

Schwergold, Caroline; Depecker, Geoffrey; Giorgio, Christophe Di; Patino, Nadia; Jossinet, Fabrice; Ehresmann, Bernard; Terreux, Raphaël; Cabrol‐Bass, Daniel; Condom, Roger

doi:10.1016/s0040-4020(02)00527-6

Cited by 40 publications

(28 citation statements)

References 43 publications

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“…To obtain all the building blocks needed to carry out the Ugi condensation, hydroxylamine 6 protected with a tert ‐butyldiphenylsilyl (TBDPS) group (Table ) was synthesized according to a literature procedure in 76 % yield Carboxymethyl nucleobases 7a – 7e (Table ) were prepared in three steps according to literature procedures, in approximately 30 % overall yield …”

Section: Resultsmentioning

confidence: 99%

Contribution to PNA–RNA Chimera Synthesis: One‐Pot Microwave‐Assisted Ugi Reaction to Obtain Dimeric Building Blocks

et al. 2016

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We report a solution‐phase synthesis of dimeric PNA–RNA (PNA = peptide nucleic acid) building blocks by using a microwave‐assisted Ugi four‐component reaction. A mixture of a functionalized amine, a carboxymethyl nucleobase, paraformaldehyde, and N4,2′‐O,3′‐O‐tribenzoyl‐5′‐deoxy‐5′‐isocyanocytidine generates the dimeric chimeras in one step. The method is simple, and gives rapid access (5 min) to diversity, as exemplified by the products described here.

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Section: Resultsmentioning

confidence: 99%

Contribution to PNA–RNA Chimera Synthesis: One‐Pot Microwave‐Assisted Ugi Reaction to Obtain Dimeric Building Blocks

et al. 2016

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“…However, in our synthesis, the fmoc group could be used as the sec ‐amine protecting group of 10 . The fmoc protection of sec ‐amine in 10 was successful, and coupling between 11 and PNA monomer 9a or 9b showed the best results in the reaction with isobutyl chloroformate (Scheme ) . After the fmoc group of 12 was removed, C* or G base was introduced by EDC coupling to yield 14 .…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Peptide Nucleic Acid Dimer Containing Modified Cytosine

Lee

Yoon

Chun

2017

Bulletin Korean Chem Soc

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“…The head-to-tail cyclization is achieved in solution by cyclizing N-terminal NH 2 group and C-terminal COOH group of the protected γ-AApeptide synthesized on the CTC (2-chlorotrityl chloride) resin [17]. The Alloc- N’ -Fmoc-N γ-AApeptide building block (Figure 2) is used as the first building block attached to the solid support, because regular Fmoc protected building block is easy to self-cleave from the solid support due to the formation of ketopiperazine side products [18]. Such side reactions can be avoided by using the Alloc protected building block because it’s removal is carried out under neutral condition.…”

Section: Synthesis Of γ-Aapeptidesmentioning

confidence: 99%

γ-AApeptides as a New Strategy for Therapeutic Development

Nimmagadda

Shi

Cai

2019

CMC

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A new class of peptidomimetics termed “γ-AApeptides” was recently developed by our group. Similar to other peptidomimetics, γ-AApeptides are resistant to proteolytic degradation, and possess limitless potential to introduce chemically diverse functional groups. γ-AApeptides have shown great promise in biomedical applications. In this article, we will review a few examples of γ-AApeptides with biological potential. Certain γ-AApeptides can permeate cell membranes and therefore they can be used as potential drug carrier. γ-AApeptides can also bind to HIV RNA with high specificity and affinity, suggesting their potential application as anti-HIV agents. Moreover, they can mimic host-defense peptides and display potent and broad-spectrum activity towards a range of drug-resistant bacterial pathogens. They are also potential anti-cancer agents. For instance, they have shown great promise in targeted imaging of tumor in mouse model, and they are also capable of disrupting p53/DNA interactions, and thus antagonize STAT3 signaling pathway. Recently, from combinatorial screening, γ-AApeptides are identified to inhibit Aβ peptide aggregation, and thus they can be developed into potential anti-Alzheimer’s Disease agent.

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Cyclic PNA hexamer-based compound: modelling, synthesis and inhibition of the HIV-1 RNA dimerization process

Cited by 40 publications

References 43 publications

Contribution to PNA–RNA Chimera Synthesis: One‐Pot Microwave‐Assisted Ugi Reaction to Obtain Dimeric Building Blocks

Contribution to PNA–RNA Chimera Synthesis: One‐Pot Microwave‐Assisted Ugi Reaction to Obtain Dimeric Building Blocks

Synthesis of Peptide Nucleic Acid Dimer Containing Modified Cytosine

γ-AApeptides as a New Strategy for Therapeutic Development

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