2012
DOI: 10.1371/journal.pone.0035774
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γ sulphate PNA (PNA S): Highly Selective DNA Binding Molecule Showing Promising Antigene Activity

Abstract: Peptide Nucleic Acids (PNAs), nucleic acid analogues showing high stability to enzyme degradation and strong affinity and specificity of binding toward DNA and RNA are widely investigated as tools to interfere in gene expression. Several studies have been focused on PNA analogues with modifications on the backbone and bases in the attempt to overcome solubility, uptake and aggregation issues. γ PNAs, PNA derivatives having a substituent in the γ position of the backbone show interesting properties in terms of … Show more

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Cited by 45 publications
(58 citation statements)
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“…[47][48][49] Among the most promising modification-with respect to the ease of chemical synthesis, functional group diversification, and conformational preorganization-was the installation of a chiral center at the γ-backbone. 45,[50][51][52][53][54][55][56][57][58][59][60] We showed that the enhancements in binding affinity and sequence selectivity of PNA upon introduction of an (S)-chiral center (prepared from L-amino acid) at this position emanate from backbone preorganization, a conformational transition from a globular fold into a RH helical motif. 61,62 However, on the basis of these initial studies with limited stereochemical exploration, it was not clear whether the helical sense of γPNA could be reversed simply by switching the chirality at the γ-backbone, and, if so, whether the resulting RH and LH conformers would be able to recognize each other, or how they would interact with DNA or RNA.…”
Section: Resultsmentioning
confidence: 99%
“…[47][48][49] Among the most promising modification-with respect to the ease of chemical synthesis, functional group diversification, and conformational preorganization-was the installation of a chiral center at the γ-backbone. 45,[50][51][52][53][54][55][56][57][58][59][60] We showed that the enhancements in binding affinity and sequence selectivity of PNA upon introduction of an (S)-chiral center (prepared from L-amino acid) at this position emanate from backbone preorganization, a conformational transition from a globular fold into a RH helical motif. 61,62 However, on the basis of these initial studies with limited stereochemical exploration, it was not clear whether the helical sense of γPNA could be reversed simply by switching the chirality at the γ-backbone, and, if so, whether the resulting RH and LH conformers would be able to recognize each other, or how they would interact with DNA or RNA.…”
Section: Resultsmentioning
confidence: 99%
“…[18] Also, Romanelli and coworkers have shown that in the case of PNA 2 :DNA triplexes containing negatively charged PNA, doubling salt concentration increases stability. [23] Thus, we anticipated that our negatively charged PNA would demonstrate positive salt dependence in duplex formation with DNA and RNA.…”
Section: Resultsmentioning
confidence: 99%
“…In the case of γ-substituted PNA, positively charged or neutral side chains increase binding affinity with DNA, [16][20] but this increase is primarily attributed to steric or hydrogen-bonding effects leading to conformational preorganization of the PNA backbone. [21], [22] There is evidence that negatively charged side chains are also tolerated at the γ-position, [17], [23] but their effect on binding affinity with DNA at varying ionic strength has not been thoroughly studied. Additionally, the binding properties of γ-substituted PNA with RNA have only been minimally investigated.…”
Section: Introductionmentioning
confidence: 99%
“…Compared to unmodified PNAs the g-modified have several advantages such us improved solubility, better permeability to cells (in particular the g-GPNAs), increased stability of PNA-DNA duplexes and opportunities for further functionalization. [108][109][110][111][112][113][114][115][116][117][118] The first example of a chiral g modified PNA monomer (Fig. 13A) was reported in 1994 by Lyang et al 108 but they started to gain attention only from 2005.…”
Section: A-modified Pna Monomermentioning
confidence: 99%
“…113 Among the sequences designed, the PNA one carrying the modified monomer at C-terminus was the most promising in the inhibitory effect to the generation of Sp1/DNA complex. 113 Romanelli et al 114 developed a novel g-sulfate PNA analog (Fig. 13E), designed to be similar to DNA in terms of polarity, charge and solubility.…”
mentioning
confidence: 99%