Some New 1-(Nitroxyalkyl)-3-nitroguanidines and their Cyclic Products<sup>1</sup>

Fishbein, Lawrence; Gallaghan, John A.

doi:10.1021/ja01641a035

Cited by 2 publications

(3 citation statements)

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“…The synthesis of 2-methacrylic acid 3-guanidino-propyl ester (GuaMA) was performed in two steps (Figure 1). In the first step, 3-aminopropanol was converted into guanidinopropanol using 2-ethyl-2-thiopseudourea hydrobromide with the release of ethanethiol (25). This reaction yielded the desired product in quantitative yield and good purity (>97% by NMR).…”

Section: Resultsmentioning

confidence: 99%

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Poly(3-guanidinopropyl methacrylate): A Novel Cationic Polymer for Gene Delivery

et al. 2004

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A cationic polymethacrylate with a guanidinium side group was designed in order to create a polymer with cell membrane-penetrating properties such as Tat or other arginine-rich peptides. The polymer, poly(3-guanidinopropyl methacrylate), abbreviated as pGuaMA, was synthesized by free radical polymerization. The DNA-condensing properties of pGuaMA (Mw 180 kDa) were investigated via dynamic light scattering and zeta potential measurements, and small, positively charged particles (110 nm, +37 mV) were found. It was shown that polyplexes based on pGuaMA were able to transfect COS-7 cells efficiently in the absence of serum, while under the same conditions poly(arginine) (pArg) polyplexes did not show detectable transfection levels. Addition of a membrane-disrupting peptide, INF 7, derived from the influenza virus, to preformed pGuaMA polyplexes did result in approximately 2 times increased transfection levels. DLS, zeta potential measurements, gel electrophoresis, and ethidium bromide displacement measurements indicated that serum induced aggregation of the polyplexes at high polymer/plasmid ratios, while at low polymer/plasmid ratios the polarity of the polyplexes reversed likely due to adsorption of negatively charged proteins on their surface. Likely, the unfavorable interactions of pGuaMA polyplexes with serum proteins is the reason for the absent transfection activity of these polyplexes in the presence of serum. Confocal laser scanning microscopy indicated cellular internalization via endocytosis of both polyplexes and free polymer. Thus, pGuaMA polyplexes enter cells, as reported for other polyplexes, by endocytosis and not, as hypothesized, via direct membrane passage.

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Section: Resultsmentioning

confidence: 99%

“…Synthesis of 2-Methacrylic Acid 3-Guanidinopropyl Ester (GuaMA). 2-Guanidinopropanol was synthesized according to Fishbein and Gallaghan (25). In detail, 3-aminopropanol (0.641 g, 8.54 mmol) was added dropwise to 2-ethyl-2-thiopseudourea hydrobromide (1.58 g, 8.54 mmol) in a 10 mL flask.…”

Section: Methodsmentioning

confidence: 99%

Poly(3-guanidinopropyl methacrylate): A Novel Cationic Polymer for Gene Delivery

et al. 2004

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“…Guanidinylated BPEI (GBPEI) was synthesized by following reported methods with some modification 12. Briefly, BPEI1.2K (1.667 mmol, 2 g) in 20 mL vials was diluted to 10 mL using deionized (DI) water.…”

Section: Methodsmentioning

confidence: 99%

Bioreducible Guanidinylated Polyethylenimine for Efficient Gene Delivery

Lee

Jeong

et al. 2014

ChemMedChem

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Cationic polymers are known to afford efficient gene transfection. However, cytotoxicity remains a problem at the molecular weight for optimal DNA delivery. As such, optimized polymeric gene delivery systems are still a sought-after research goal. A guanidinylated bioreducible branched polyethylenimine (GBPEI-SS) was synthesized by using a disulfide bond to crosslink the guanidinylated BPEI (GBPEI). GBPEI-SS showed sufficient plasmid DNA (pDNA) condensation ability. The physicochemical properties of GBPEI-SS demonstrate that it has the appropriate size (~200 nm) and surface potential (~30 mV) at a nitrogen-to-phosphorus ratio of 10. No significant toxicity was observed, possibly due to bioreducibility and to the guanidine group delocalizing the positive charge of the primary amine in BPEI. Compared with the nonguanidinylated analogue, BPEI-SS, GBPEI-SS showed enhanced transfection efficiency owing to increased cellular uptake and efficient pDNA release by cleavage of disulfide bonds. This system is very efficient for delivering pDNA into cells, thereby achieving high transfection efficiency and low cytotoxicity.

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Some New 1-(Nitroxyalkyl)-3-nitroguanidines and their Cyclic Products¹

Cited by 2 publications

References 3 publications

Poly(3-guanidinopropyl methacrylate): A Novel Cationic Polymer for Gene Delivery

Poly(3-guanidinopropyl methacrylate): A Novel Cationic Polymer for Gene Delivery

Bioreducible Guanidinylated Polyethylenimine for Efficient Gene Delivery

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Some New 1-(Nitroxyalkyl)-3-nitroguanidines and their Cyclic Products1

Cited by 2 publications

References 3 publications

Poly(3-guanidinopropyl methacrylate): A Novel Cationic Polymer for Gene Delivery

Poly(3-guanidinopropyl methacrylate): A Novel Cationic Polymer for Gene Delivery

Bioreducible Guanidinylated Polyethylenimine for Efficient Gene Delivery

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Some New 1-(Nitroxyalkyl)-3-nitroguanidines and their Cyclic Products¹