Sulfonium and phosphonium, new ion-pairing agents with unique selectivity towards polarizable anions

Harrison, Christopher R.; Sader, Jayden A.; Lucy, Charles A.

doi:10.1016/j.chroma.2006.01.132

Cited by 21 publications

(12 citation statements)

References 30 publications

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“…Small ~10 nm nano-complexes were formed with the addition of TBPB (Figure S1), while without it nano-complexes were 300 nm for the 8:1 N:P ratio of Tat 2 :dsRNA. It can be postulated that TBPB acts as a low concentration effective chaotropic, as shown previously (Harrison et al, 2006), breaking apart larger aggregates into smaller particles. This mechanism of action is substantiated as it is shown to only display substantial effects with linear dsDNA smaller than 3 kb.…”

Section: Discussionsupporting

confidence: 56%

Tetrabutylphosphonium Bromide Reduces Size and Polydispersity Index of Tat2:siRNA Nano-Complexes for Triticale RNAi

Pepper

Maheshwari

Ziemienowicz

et al. 2017

Front. Mol. Biosci.

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Cell-penetrating peptides (CPPs) are short 8–30 amino-acid oligopeptides that act as effective transducers of macromolecular cargo, particularly nucleic acids. They have been implemented in delivering dsDNA, ssDNA, and dsRNA into animal and plant cells. CPPs and nucleic acids form nano-complexes that are often 100–300 nm in size but still effectively transit the cell membrane of animal cells, but are less effective with plant cells due to the plant cell wall. To overcome this obstacle, nano-complexes of the CPP Tat2 and various lengths of nucleic acid (21-mer siRNA duplex (dsRNA) to ~5.5 kb circular plasmid) were evaluated for size using dynamic light scattering (DLS), under conditions of increasing ionic strength (Ic) and addition of phase transfer catalyst salts (tetrabutylammonium bromide-TBAB and tetrabutylphosphonium bromide-TBPB) and sugars (maltose-mannitol solution). It was found that the combination of 21-mer siRNA:Tat2 complexes with TBPB produced small 10–20 nm diameter nano-complexes with a polydispersity index (PDI) of ~0.1. Furthermore, it was found that for each length of nucleic acid that a linear mathematical relationship existed between the theoretical volume of the nano-complex and the nucleic acid length. Next, nano-complex formulation was tested for its ability to carry small interfering RNA molecules into plant cells and to trigger silencing of phytoene desaturase (PDS) in Triticale leaves. RT-qPCR showed 75% suppression of PDS, demonstrating that TBPB acts as an adjuvant in effecting the entry and efficacy of siRNA in young Triticale plants.

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Section: Discussionsupporting

confidence: 56%

Tetrabutylphosphonium Bromide Reduces Size and Polydispersity Index of Tat2:siRNA Nano-Complexes for Triticale RNAi

Pepper

Maheshwari

Ziemienowicz

et al. 2017

Front. Mol. Biosci.

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“…We sought to improve phosphopeptide retention under alkaline conditions through the use of aliphatic-functionalized quaternary amines as ion pairing agents, and found that tetrapropylammonium ion completely abrogated breakthrough of phosphopeptides; moreover, we observed that peptide elution order from the first dimension column was well correlated with both the degree of phosphorylation and relative acidic content (D and E) of phosphopeptides. Despite the successful use of ion pairing chromatography in the analysis of a wide range of molecule classes (50,54,97), we observed significant fraction-to-fraction overlap of phosphopeptides in RP-RP fractionation augmented with tetrapropylammonium formate, suggesting that further optimization will be required to utilize these compounds for the analysis of complex biological lysates.…”

Section: Discussionmentioning

confidence: 74%

Online Nanoflow Multidimensional Fractionation for High Efficiency Phosphopeptide Analysis

Ficarro

Zhang

Carrasco-Alfonso

et al. 2011

Molecular & Cellular Proteomics

110

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Despite intense, continued interest in global analyses of signaling cascades through mass spectrometry-based studies, the large-scale, systematic production of phosphoproteomics data has been hampered in-part by inefficient fractionation strategies subsequent to phosphopeptide enrichment. Here we explore two novel multidimensional fractionation strategies for analysis of phosphopeptides. In the first technique we utilize aliphatic ion pairing agents to improve retention of phosphopeptides at high pH in the first dimension of a twodimensional RP-RP. The second approach is based on the addition of strong anion exchange as the second dimension in a three-dimensional reversed phase ( Reversible phosphorylation plays a central role in the regulation of normal cell physiology. The strong links between aberrant signaling and human disease, along with the potential for specific inhibition of disrupted kinase activity, continue to drive efforts aimed at systematic and largescale analysis of phosphorylation in cells and tissues. Shortly after introduction of immobilized metal affinity chromatography (IMAC) 1 as an enrichment tool prior to mass spectrometry (MS) analysis (1-3), several laboratories demonstrated the feasibility of phosphopeptide identification and quantitation en masse (4 -7). In the ensuing years, despite widespread proliferation of improved and innovative (8 -14) phosphoproteomics methods, the field struggled with low specificity and poor reproducibility within and across protocols and laboratories. These limitations effectively made dynamic range a secondary issue for the majority of studies. Over the past ca. 5 years, the performance of phosphopeptide enrichment protocols and related methods has stabilized; in fact several groups (15-23) have successfully coupled phosphopeptide enrichment with online or offline fractionation schemes to achieve, in some cases, over 10,000 phosphopeptide identifications. Although these strategies provide for larger phosphosite catalogs, closer inspection reveals that the analytical efficiency, as measured by the number of phosphopeptide identifications per microgram of biological lysate consumed, has remained surprisingly consistent at Ϸ1-10 phosphopeptides/g across a wide range of sample types (Table I). One explanation is that the physicochemical properties of phosphopeptides render them less amenable to fractionation by commonly used techniques. For example, although the combination of strong cation exchange (SCX) with reversed phase (RP) has been tremendously successful for 1 The abbreviations used are: IMAC, immobilized metal affinity chromatography; AML, Acute Myeloid Leukemia; CAD, collisionally activated dissociation; ESI, electrospray ionization; FDR, False Discovery Rate; FL, FLT3 ligand; FLT3, FMS-like tyrosine kinase 3; LC/MS, liquid chromatography/mass spectrometry; Lm-OVA, Recombinant Listeria monocytogenes expressing chicken ovalbumin; ITD, internal tandem duplication; MS/MS, mass spectrometry/mass spectrometry or tandem mass spectrometry; NTA, nitrilotetra...

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“…The observed difference in the magnitude of the EOF change may be explained by the ability of each anion to form an ion pair with TMA. It is known that the more hydrophobic the anion, the more effectively it can ion pair with a cation . In comparing a composite of known Hofmeister series containing three of the four anions studied , we can see that the most hydrophilic anions (e.g.…”

Section: Resultsmentioning

confidence: 91%

Adsorption of buffer ion pairs can alter long‐term electroosmotic flow stability

Morris

Harrison

2013

Electrophoresis

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Dynamic capillary coatings have become widespread due to their efficacy in modifying the EOF in capillary electrophoretic separations and ability to limit unwanted analyte-surface interactions. However, our understanding of exactly what types of interactions are taking place at the surface of a capillary when these dynamic additives are present is limited. In this work, we have chosen a simple, small molecule additive, tetramethylammonium to examine its influence on the EOF under typical separation conditions. What we have revealed is that this simple compound does not interact with the capillary surface in a very simple manner. Our initial hypothesis of a direct ionic interaction with the silanol surface has evolved with evidence of complex ion pairing between the silanols, the tetramethylammonium, and the buffer ions. This ion pairing can result in drastic changes in the EOF over time, and that the EOF can only be restored to initial levels with harsh rinses containing sodium hydroxide.

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Sulfonium and phosphonium, new ion-pairing agents with unique selectivity towards polarizable anions

Cited by 21 publications

References 30 publications

Tetrabutylphosphonium Bromide Reduces Size and Polydispersity Index of Tat2:siRNA Nano-Complexes for Triticale RNAi

Tetrabutylphosphonium Bromide Reduces Size and Polydispersity Index of Tat2:siRNA Nano-Complexes for Triticale RNAi

Online Nanoflow Multidimensional Fractionation for High Efficiency Phosphopeptide Analysis

Adsorption of buffer ion pairs can alter long‐term electroosmotic flow stability

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