Novel dextran derivatives with unconventional structure formed in an efficient one-pot reaction

Hotzel, Konrad; Heinze, Thomas

doi:10.1016/j.carres.2016.08.007

Cited by 4 publications

(11 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…formed, which are interesting nonviral gen-transfer vectors (Figure 5b). [102] Furthermore, the ring-opening of lactams in the presence of p-toluenesulphonic acid chloride is an efficient path to obtain cationic cellulose esters with DS in the range from 0.24 to 1.17. [103] The transformation of cellulose can be carried out homogenously in N-methyl-2-pyrrolidone (NMP)/LiCl or 1-butyl-3-methylimidazolium chloride containing NMP, with N-methyl-2-piperidone, ε-caprolactam and N-methyl-εcaprolactam as reactive lactams forming a reactive intermediate in the presence of tosyl chloride according to the Vilsmeier-Haack reaction (Figure 5c).…”

Section: Positively Charged Ionic Cellulose Derivativesmentioning

confidence: 99%

Recent Progress on Cellulose‐Based Ionic Compounds for Biomaterials

Yang

Zeng

et al. 2020

Advanced Materials

Self Cite

View full text Add to dashboard Cite

Cellulose and hemicelluloses represent the most abundant biomaterials on the Earth and represent major structural components in cell walls of plant that provide them with sufficient mechanical Glycans play important roles in all major kingdoms of organisms, such as archea, bacteria, fungi, plants, and animals. Cellulose, the most abundant polysaccharide on the Earth, plays a predominant role for mechanical stability in plants, and finds a plethora of applications by humans. Beyond traditional use, biomedical application of cellulose becomes feasible with advances of soluble cellulose derivatives with diverse functional moieties along the backbone and modified nanocellulose with versatile functional groups on the surface due to the native features of cellulose as both cellulose chains and supramolecular ordered domains as extractable nanocellulose. With the focus on ionic cellulose-based compounds involving both these groups primarily for biomedical applications, a brief introduction about glycoscience and especially native biologically active glycosaminoglycans with specific biomedical application areas on humans is given, which inspires further development of bioactive compounds from glycans. Then, both polymeric cellulose derivatives and nanocellulose-based compounds synthesized as versatile biomaterials for a large variety of biomedical applications, such as for wound dressings, controlled release, encapsulation of cells and enzymes, and tissue engineering, are separately described, regarding the diverse routes of synthesis and the established and suggested applications for these highly interesting materials.

show abstract

Section: Positively Charged Ionic Cellulose Derivativesmentioning

confidence: 99%

Recent Progress on Cellulose‐Based Ionic Compounds for Biomaterials

Yang

Zeng

et al. 2020

Advanced Materials

Self Cite

View full text Add to dashboard Cite

show abstract

“…Cationic dextran derivatives containing formamidine ester moieties (DEXfa, Scheme 1 ) were prepared with the recently reported simple, fast and efficient one pot synthesis. [ 23 ] As backbone pharmaceutical grade dextran B‐512F by Leuconostoc mesenteroides with a molar mass of 60 000 g mol −1 was selected. This type of dextran was already successfully used as the basis for gene delivery agents in studies before, especially in combination with different cationic amino acids.…”

Section: Resultsmentioning

confidence: 99%

“…An extensive description of the polymer synthesis and characterization can be found in Hotzel et al. [ 23 ]…”

Section: Resultsmentioning

confidence: 99%

“…[ 26 ] The p K a of the dextran‐formamidine esters represented here is 10.1 as measured earlier by potentiometric titration. [ 23 ] In contrast to the tetrahedral amino moieties with located protons, amidines present a planar structure with delocalized charge. Thus, they are more suited to form hydrogen bonds, which is suggested to enable, e.g., improved interactions with receptors at the surface of cells.…”

Section: Resultsmentioning

confidence: 99%

“…They were synthesized in an efficient one‐pot reaction where functional groups of beta‐alanine were selectively converted by iminium chloride as reported before. [ 23 ] Physicochemical characteristics of the complexes, interaction with and protection of plasmid DNA (pDNA), transfection efficiency as well as aspects of cyto‐ and hemocompatibility were investigated to get insight into the suitability of formamidine dextran esters as nonviral vectors.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

The Role of Formamidine Groups in Dextran Based Nonviral Vectors for Gene Delivery on Their Physicochemical and Biological Characteristics

Fischer

Dusek

Hotzel

et al. 2020

Macromolecular Bioscience

Self Cite

View full text Add to dashboard Cite

Dextran‐formamidine esters (dextran‐N‐[(dimethylamino)methylene]‐β‐alanine ester) with different degrees of substitution (0.45–0.92) are synthesized in an one‐pot reaction. Dextran (Mw 60 000 g mol−1) is allowed to react with unprotected beta‐alanine and iminium chloride and investigated regarding the potential as gene delivery system for the transfer of plasmid DNA. With degrees of substitution ≥ 0.63 improved DNA binding with formation of enzymatically stable complexes of about 130–160 nm with negative surface charges are obtained. These physicochemical characteristics correlated with increasing transfection rates in CHO‐K1 cells determined by a luciferase reporter gene assay in dependency of the number of formamidine residues, N/P ratios and amount of DNA. The role of the number of formamidine groups is also highlighted by in vitro cyto‐ and hemotoxicity tests under the chosen conditions. These results indicate that dextran‐formamidine esters are a very promising material for the safe and efficient gene delivery.

show abstract

Bone metastasis target redox-responsive micell for the treatment of lung cancer bone metastasis and anti-bone resorption

Zhao

Cheng

et al. 2018

Artificial Cells, Nanomedicine, and Biotechnology

View full text Add to dashboard Cite

In order to inhibit the growth of lung cancer bone metastasis and reduce the bone resorption at bone metastasis sites, a bone metastasis target micelle DOX@DBMs-ALN was prepared. The size and the zeta potential of DOX@DBNs-ALN were about 60 nm and -15 mV, respectively. DOX@DBMs-ALN exhibited high binding affinity with hydroxyapatite and released DOX in redox-responsive manner. DOX@DBMs-ALN was effectively up taken by A549 cells and delivered DOX to the nucleus of A549 cells, which resulted in strong cytotoxicity on A549 cells. The in vivo experimental results indicated that DOX@DBMs-ALN specifically delivered DOX to bone metastasis site and obviously prolonged the retention time of DOX in bone metastasis site. Moreover, DOX@DBMs-ALN not only significantly inhibited the growth of bone metastasis tumour but also obviously reduced the bone resorption at bone metastasis sites without causing marked systemic toxicity. Thus, DOX@DBMs-ALN has great potential in the treatment of lung cancer bone metastasis.

show abstract

Novel dextran derivatives with unconventional structure formed in an efficient one-pot reaction

Cited by 4 publications

References 15 publications

Recent Progress on Cellulose‐Based Ionic Compounds for Biomaterials

Recent Progress on Cellulose‐Based Ionic Compounds for Biomaterials

The Role of Formamidine Groups in Dextran Based Nonviral Vectors for Gene Delivery on Their Physicochemical and Biological Characteristics

Bone metastasis target redox-responsive micell for the treatment of lung cancer bone metastasis and anti-bone resorption

Contact Info

Product

Resources

About