Dendronised block copolymers as potential vectors for gene transfection

Wigglesworth, Tony J.; Teixeira, Francisco José Soares; Axthelm, Fabian; Eisler, Sara; Csaba, Nœmi; Merkle, Hans P.; Meier, Wolfgang; Diederich, François

doi:10.1039/b802808g

Cited by 16 publications

(10 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Agarose Gel Electrophoresis. 38 170 ng of pDNA and 10 μL of 12.5, 25, and 50 μM gemini surfactants 12-16 solution was loaded with 5 μL glycerol into 1% agarose gel containing 2 μL of ethidium bromide (0.5 mg/mL). Electrophoresis was carried out at 100 V in Tris buffer for 30 min.…”

Section: Methodsmentioning

confidence: 99%

Novel Gemini Pyridinium Surfactants: Synthesis and Study of Their Surface Activity, DNA Binding, and Cytotoxicity

2009

View full text Add to dashboard Cite

New pyridinium gemini amphiphiles having ethane-1,2-dithiol spacer have been synthesized by regioselective electrophilic cobromination of alpha-olefins. Ethane-1,2-dithiol (1) and N-bromosuccinimide (6) on reaction with alpha-olefins (dodecene (2), tetradecene (3), hexadecene (4), and octadecene (5)) gave the respective 1,2-bis(2-bromoalkylthio)ethane (7-10). The bromoalkylthio ethers when reacted with pyridine (11) gave the respective gemini bispyridinium bromide (12-15). The surface properties of new geminis were evaluated by surface tension and conductivity measurements. These gemini surfactants have also been found to be having low cytotoxicity by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay on C6 glioma cells. The DNA binding capabilities of these amphiphiles have been determined below as well as above critical micelle concentration. The preliminary studies by agarose gel electrophoresis indicated chain length dependent DNA binding abilities which has further been proved by ethidium bromide exclusion experiments and transmission electron microscopy (TEM).

show abstract

Section: Methodsmentioning

confidence: 99%

Novel Gemini Pyridinium Surfactants: Synthesis and Study of Their Surface Activity, DNA Binding, and Cytotoxicity

2009

View full text Add to dashboard Cite

show abstract

“…This study focuses on a new flexible approach for the synthesis of drug delivery submicroparticles functionalized by several molecules (therapeutic agent, fluorescent dye, etc) using a standardized procedure and nonaggressive methodology based on click chemistry and Ring‐Opening Metathesis Polymerization (ROMP). Recently, several authors6–12 have shown that ROMP polymers can be functionalized by “click‐chemistry” either by functionalizing the monomer or after polymerization of a precursor monomer bearing an alkyl bromide. Nevertheless, to the best of our knowledge, combination of ROMP and “click‐chemistry” has never been reported in dispersed media.…”

Section: Introductionmentioning

confidence: 99%

Easy and effective method to produce functionalized particles for cellular uptake

Collette

Delatouche

Blanquart

et al. 2012

J. Polym. Sci. A Polym. Chem.

View full text Add to dashboard Cite

International audienceIn this contribution, a versatile approach for the synthesis of functionalized particles for drug delivery is presented, using two nonaggressive standardized procedures. The first procedure considered is the functionalization of an azido-terminated α-norbornenyl poly(ethylene oxide) (PEO) macromonomer with an alkyne-containing active molecule via the copper catalyzed azide alkyne cycloaddition, click type reaction. The functionalized macromonomer is then polymerized by Ring-Opening Metathesis Polymerization (ROMP) in dispersion to form functionalized particles. The second procedure consists in synthesizing particles by ROMP in dispersed media of norbornene with azido-terminated α-norbornenyl PEO macromonomer. The ROMP was initiated by the first generation Grubbs catalyst. Such functionalized core-shell particles have stealthy properties due to their PEO shell and can be viewed as universal nanocarriers on which any alkyne-modified active molecule can be grafted by click chemistry. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 201

show abstract

“…The norbornene benzylic bromide precursor ( 4 , Scheme ) was prepared by monosubstitution of α,α′-dibromo- p -xylene ( 1 , Scheme ) with the sodium anion of (±)- exo -5-norbornene-2-methanol . The exo -adduct was used as the steric hindrance around the carbon–carbon double bond is less than in the case of the endo -compound, enabling an easier approach of reactants during the postpolymerization modification (e.g., thiyl radicals in thiol–ene chemistry).…”

Section: Resultsmentioning

confidence: 99%

“…Compound 4 (Scheme ) was prepared by a reported procedure, starting from distilled (±)- exo -5-norbornene-2-methanol . The synthesis was repeated on 5 g scale and compound 4 was isolated after column chromatography with 53% yield.…”

Section: Methodsmentioning

confidence: 99%

Norbornenyl-Based RAFT Agents for the Preparation of Functional Polymers via Thiol–Ene Chemistry

et al. 2011

View full text Add to dashboard Cite

A synthetic platform for the preparation of various norbornenyl (Nb) containing reversible additionÀfragmentation chain transfer (RAFT) agents has been developed. The design of the chain transfer agents (CTAs) is based on the desymmetrization of R,R 0 -dibromo-p-xylene by monosubstitution with an alkoxide anion and subsequent replacement of the residual bromine atom in the benzylic bromide to create several series of RAFT CTA including trithiocarbonate, xanthate and dithiobenzoate CTAs, allowing for the possibility to introduce other functional groups besides Nb, such as an allyl group. While a norbornene functionality was chosen as most reactive functional group toward thiols in radical-mediated thiolÀene chemistry, an allyl group was introduced for the sake of direct comparison of the double bond reactivity in the thiolÀene reaction. Control of the radical polymerization of acrylates, styrene and vinyl acetate has been achieved by using this novel family of CTAs. The results indicate that the Nb group remained intact at low monomer conversions (e.g., below 50% for styrene and vinyl acetate, below 30% for acrylates) and at optimal reaction temperatures (e.g., 70 °C for styrene and vinyl acetate, 62 and 65 °C for 1-ethoxyethyl acrylate and methyl acrylate, respectively), while the monomer-to-CTA ratio was kept high. Polymers with high end-group fidelity were modified with a series of thiol-containing compounds, leading to R-semitelechelics with different chain-end structures. While allyl-containing polymers exhibited a significantly lower reactivity, modification of the Nb-containing semitelechelics was rapid and fully accomplished under the same reaction conditions. However, for the given conditions, dodecanethiol and benzyl mercaptan showed a lower reactivity toward Nb-containing polymers, as evidenced by the obtained modification efficiency of 70% and 45%, respectively.

show abstract

Dendronised block copolymers as potential vectors for gene transfection

Cited by 16 publications

References 28 publications

Novel Gemini Pyridinium Surfactants: Synthesis and Study of Their Surface Activity, DNA Binding, and Cytotoxicity

Novel Gemini Pyridinium Surfactants: Synthesis and Study of Their Surface Activity, DNA Binding, and Cytotoxicity

Easy and effective method to produce functionalized particles for cellular uptake

Norbornenyl-Based RAFT Agents for the Preparation of Functional Polymers via Thiol–Ene Chemistry

Contact Info

Product

Resources

About