Synthesis of Novel Diselenide‐Linked Porphyrin Dimers under Phase‐Transfer Catalysis Condition and Their Interactions with DNA

Xue, Zhi; Kwong, Daniel W. J.; Xue, Ling-Wei; Liu, Qing; Hou, An-Xin; Wong, Wai‐Kwok

doi:10.1002/cbdv.200800182

Cited by 5 publications

(3 citation statements)

References 27 publications

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“…37,38 Selenium powder (2.37 g, 30 mmol) in 10 mL of water was added to a three-necked flask under a nitrogen atmosphere. NaBH 4 (2.27 g, 60 mmol) dissolved in 25 mL of cold H 2 O was syringed dropwise into the selenium suspension.…”

Section: Materials and Methods Materialsmentioning

confidence: 99%

“…27,29,[34][35][36][37] After it was found that low molecular weight oligoethylenimine (OEI) cross-linked by dithiobis (succinimidylpropionate) or dimethyl ⋅ 3,3′-dithiobispropionimidate ⋅ 2HCl achieved highly efficient transfection in vitro and had lower cytotoxicity, 34 much research attention has been focused on modification of different disulfide bonds containing linkers [27][28][29]35 and effect of the molecular weight of cross-linked OEI. 35 Inspired by the success of disulfide bonds, the selenium (Se) element listed in the same family as sulfur (S) in the periodic table of elements has attracted attention.…”

Section: Introductionmentioning

confidence: 99%

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Development of a reduction-sensitive diselenide-conjugated oligoethylenimine nanoparticulate system as a gene carrier

Gu¹

2012

IJN

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Background:The reduction-sensitive cationic polymer is a promising nonviral carrier for gene delivery. Until now, disulfide bonds have been the only golden standard for its design. The aim of this research was to develop a novel reduction-responsive cationic polymer as a gene carrier. Methods: Polycationic carriers were synthesized by addition of branched oligoethylenimine 800 Da (OEI 800 ) via an active ester containing diselenide bonds. Disulfide bonds cross-linked with OEI 800 -SS x and monoselenide bonds linked with OEI 800 -Se x were synthesized and compared. Their molecular weights and degradation properties were determined using gel permeation chromatography. Changes in particle size, morphology, and DNA binding were investigated by dynamic light scattering, transmission electron microscopy, and electrophoresis assay in a reduction environment. Cytotoxicity and transfection in vitro were evaluated in a murine melanoma cell line (B16F10) and a human cervical epithelial carcinoma cell line (HeLa), while intracellular degradation and dissociation with DNA were studied by confocal laser scanning microscopy with FITC-labeled OEI 800 derivatives and Cy5-labeled DNA. Results: Diselenide-conjugated OEI 800 (OEI 800 -SeSe x ) polymer carriers of high molecular weight were successfully synthesized. After compacting with DNA, the OEI 800 -SeSe x polymers formed nanoparticles with an average size of 140 nm at an adequate C/P ratio. OEI 800 -SeSe x showed reduction-responsive degradation properties similar to those of the OEI 800 -SS x via gel permeation chromatography, dynamic light scattering, and transmission electron microscopy. OEI 800 -SeSe x showed much lower cytotoxicity than PEI 25k , and significantly higher transfection efficiency than OEI 800 in both B16F10 and HeLa cells. Transfection of luciferase in the OEI 800 -SeSe x group was comparable with that of standard PEI 25k and traditional reduction-sensitive polymer OEI 800 -SS x groups. Furthermore, intracellular degradation of OEI 800 -SeSe x and dissociation with DNA were also confirmed by confocal laser scanning microscopy. Conclusion:The OEI 800 -SeSe x obtained was able to bind plasmid DNA efficiently to yield nanosized particles and had reduction sensitivity which is as efficient as that for OEI 800 -SS x . In vitro experiments confirmed its low cytotoxicity and high transfection ability. Diselenide bonds can be used as effective and novel reduction-sensitive linkages for gene delivery.

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Section: Materials and Methods Materialsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Development of a reduction-sensitive diselenide-conjugated oligoethylenimine nanoparticulate system as a gene carrier

Gu¹

2012

IJN

View full text Add to dashboard Cite

show abstract

“…To our knowledge, only porphyrins replaced with alkylselenium groups have been synthesized, but no alkylselenium phthalocyanines have been reported. 5,[11][12][13][14][15] Based on these results, further studies have been initiated to investigate the synthesis and spectroscopic properties of a novel selenium derivatized zinc(II) phthalocyanine complex to evaluate its properties as a potential photosensitizer for clinical purposes.…”

Section: Introductionmentioning

confidence: 99%