Water soluble cationic dextran derivatives containing poly(amidoamine) dendrons for efficient gene delivery

Mai, Kaijin; Zhang, Shanshan; Liang, Bing; Gao, Cong; Du, Wenjun; Zhang, Liming

doi:10.1016/j.carbpol.2015.01.042

Cited by 14 publications

(11 citation statements)

References 31 publications

(31 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cationic polysaccharides are materials of interest for a number of applications, ranging from industrial (e.g., flocculants (Pal, Mal & Singh, 2005) and anti-bacterial coatings (Dilamian, Montazer & Masoumi, 2013)) to biomedical (e.g., vehicles for gene delivery (Ikeda, Minari, Shimada, Numata, Sakurai & Shinkai, 2007;Mai, Zhang, Liang, Gao, Du & Zhang, 2015) and for delivery of anionic drugs (Bernkop-Schnurch & Dunnhaupt, 2012;Tamaru, Tokunaga, Hori, Matsuda & Shinkai, 2014)). Despite the potential utility of such materials, there are relatively few synthetic approaches to cationic polysaccharides, especially to those that carry a permanent positive charge (and thus are charged even at neutral pH).…”

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis of cationic 6-deoxy-6-(N,N,N-trialkylammonio)curdlan derivatives

Zhang

Liu

Edgar

2016

Carbohydrate Polymers

View full text Add to dashboard Cite

Curdlan, a bioactive β-1,3-glucan, is of intense interest for pharmaceutical and biomedical applications. Cationic derivatives of curdlan and other polysaccharides are especially attractive for their potential to interact in controlled fashion with proteins, among many other possible applications, but relatively few methods exist for their synthesis. Herein we report a regioselective method for preparation of cationic, water-soluble 6-(N,N,N-trialkylammonio)-6-deoxycurdlan salts by reaction of 6-bromo-6-deoxycurdlan and its 2,4-O-diesters with trialkylamines. Dimethyl sulfoxide was identified as the optimal solvent for this nucleophilic displacement to produce cationic curdlan derivatives (80 °C, 24h), providing maximum degree of triethylammonium substitution (DS) of 0.89, exclusively at the C-6 position. 6-Bromo-6-deoxycurdlan was also reacted with heterocyclic amines such as pyridine and imidazole, providing ammonium-substituted curdlan derivatives with substantial DS (0.66 and 0.86, respectively). The new combination of regioselective Furuhata bromination and bromine displacement under optimized conditions with tertiary amines provides access to quaternized curdlan derivatives that possess high, permanent positive charge and are readily water-soluble, properties that indicate potential application promise including for mucoadhesion, permeation enhancement, and delivery of genes and anionic drugs. Regioselectivity and DS of those curdlan ammonium derivatives were quantified by means of (1)H NMR, (13)C NMR and FTIR spectroscopic methods and by elemental analysis.

show abstract

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis of cationic 6-deoxy-6-(N,N,N-trialkylammonio)curdlan derivatives

Zhang

Liu

Edgar

2016

Carbohydrate Polymers

View full text Add to dashboard Cite

show abstract

“…Positive charge can also be introduced to the carrier core by addition of synthetic polymers such as polyethylenimine (PEI), [64,92,147,93,111,127,[142][143][144][145][146] polyurethane, [148] amino poly(glycerol methacrylate), [149] or positively charged dendrons. [150,151] Due to the high density of positive charges,h igh buffering capacity,a nd availability,P EI is aw idely explored synthetic polyamine in DNAd elivery and frequently termed as the "gold-standard" in polymer-mediated gene delivery. [152] In addition, covalent functionalisation of biopolymers with positively charged amino acids,p eptides,o rs mall molecules (Figure 6) can be used for charge tuning.F or example, arginine,histidine,and lysine were employed to functionalise dextran, [153][154][155] chitosan, [51] alginate, [59] human serum albumin (HSA), [78,156] HA, [116] and chondroitin sulfate.…”

Section: Polysaccharidesmentioning

confidence: 99%

“…Positive charge can also be introduced to the carrier core by addition of synthetic polymers such as polyethylenimine (PEI), [64, 92, 147, 93, 111, 127, 142–146] polyurethane, [148] amino poly(glycerol methacrylate), [149] or positively charged dendrons [150, 151] . Due to the high density of positive charges, high buffering capacity, and availability, PEI is a widely explored synthetic polyamine in DNA delivery and frequently termed as the “gold‐standard” in polymer‐mediated gene delivery [152] .…”

Section: Biopolymers As Dna Vaccine Carriersmentioning

confidence: 99%

Biopolymer‐based Carriers for DNA Vaccine Design

et al. 2021

View full text Add to dashboard Cite

She studied chemistry at the University of Zagreb, and completed her PhD at the University of Strathclyde,G lasgow,w orking on DNA detection by advanced spectroscopies, such as SERRS. After postdoc research on DNA nanostructuring and artificial enzyme design at the University of Dortmund,s he was agroup leader at Karlsruhe Institute of Technology before joining Cambridge. Her research focuses on nanostructured biomaterials for use in photocatalysis and targeted drug delivery.

show abstract

“…[1][2][3] They can be obtained directly after extraction/purification steps from natural matrix as chitosan [4,5] or by chemical or enzymatic modification of neutral or anionic carbohydrates such as alginate, dextran, pullulan, cellulose, cycloamylose, carboxymethylcellulose or also hyaluronic acid. [6][7][8][9][10] Their applications are various ranging from agro-alimentary to medicine. A particular attractive field which has constantly gained interest is the capacity of some of them to efficiently compact polynucleic acids such as DNA/RNA acting as potential non-viral gene delivery agents.…”

Section: Introductionmentioning

confidence: 99%

“…A particular attractive field which has constantly gained interest is the capacity of some of them to efficiently compact polynucleic acids such as DNA/RNA acting as potential non-viral gene delivery agents. [8,9,[11][12][13][14] Nevertheless, synthesis of such architectures requires several time consuming steps and the use of often heterogeneous starting materials. One relevant solution consists to use molecules with both well-defined structure and size to efficiently delineate a structure/activity relationship.…”

Section: Introductionmentioning

confidence: 99%

Toward a suitable structural analysis of gene delivery carrier based on polycationic carbohydrates by electron transfer dissociation tandem mass spectrometry

Przybylski

Benito

Bonnet

et al. 2016

Analytica Chimica Acta

View full text Add to dashboard Cite

Polycationic carbohydrates represent an attractive class of biomolecules for several applications and particularly as non viral gene delivery vectors. In this case, the establishment of structure-biological activity relationship requires sensitive and accurate characterization tools to both control and achieve fine structural deciphering. Electrospray-tandem mass spectrometry (ESI-MS/MS) appears as a suitable approach to address these questions. In the study herein, we have investigated the usefulness of electron transfer dissociation (ETD) to get structural data about five polycationic carbohydrates demonstrated as promising gene delivery agents. A particular attention was paid to determine the influence of charge states as well as both fluoranthene reaction time and supplementary activation (SA) on production of charge reduced species, fragmentation yield, varying from 2 to 62%, as well as to obtain the most higher both diversity and intensity of fragments, according to charge states and targeted compounds. ETD fragmentation appeared to be mainly directed toward pending group rather than carbohydrate cyclic scaffold leading to a partial sequencing for building blocks when amino groups are close to carbohydrate core, but allowing to complete structural deciphering of some of them, such as those including dithioureidocysteaminyl group which was not possible with CID only. Such findings clearly highlight the potential to help the rational choice of the suitable analytical conditions, according to the nature of the gene delivery molecules exhibiting polycationic features. Moreover, our ETD-MS/MS approach open the way to a fine sequencing/identification of grafted groups carried on various sets of oligo-/polysaccharides in various fields such as glycobiology or nanomaterials, even with unknown or questionable extraction, synthesis or modification steps.

show abstract

Water soluble cationic dextran derivatives containing poly(amidoamine) dendrons for efficient gene delivery

Cited by 14 publications

References 31 publications

Regioselective synthesis of cationic 6-deoxy-6-(N,N,N-trialkylammonio)curdlan derivatives

Regioselective synthesis of cationic 6-deoxy-6-(N,N,N-trialkylammonio)curdlan derivatives

Biopolymer‐based Carriers for DNA Vaccine Design

Toward a suitable structural analysis of gene delivery carrier based on polycationic carbohydrates by electron transfer dissociation tandem mass spectrometry

Contact Info

Product

Resources

About