Guanidinylation: A simple way to fabricate cell penetrating peptide analogue‐modified chitosan vector for enhanced gene delivery

Zhai, Xinyun; Sun, Peng; Luo, Yongfeng; Ma, Chunyang; Xu, Jun; Liu, Wenguang

doi:10.1002/app.34156

Cited by 38 publications

(19 citation statements)

References 57 publications

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“…This result may because in the reaction process of reaction, as the pH value of the system decreases, it is not conducive to the guanidinylation reaction. Guanidine functionalized chitosan can also be synthesized by the reaction of chitosan with cyanamide in aqueous phase (Salama, Saad, & Sabaa, 2017Zhai et al, 2011). However, due to the hydrolysis of cyanamide in water, the excessive amount of cyanamide is required, which makes workup difficult and the DS of the desired chitosan derivatives prepared by this method is also not very high.…”

Section: Introducing Guanidine Groupsmentioning

confidence: 99%

Cationic chitosan derivatives as potential antifungals: A review of structural optimization and applications

Qin

Guo

2020

Carbohydrate Polymers

127

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The increasing resistance of pathogen fungi poses a global public concern. There are several limitations in current antifungals, including few available fungicides, severe toxicity of some fungicides, and drug resistance. Therefore, there is an urgent need to develop new antifungals with novel targets. Chitosan has been recognized as a potential antifungal substance due to its good biocompatibility, biodegradability, non-toxicity, and availability in abundance, but its applications are hampered by the low charge density results in low solubility at physiological pH. It is believed that enhancing the positive charge density of chitosan may be the most effective approach to improve both its solubility and antifungal activity. Hence, this review mainly focuses on the structural optimization strategy of cationic chitosan and the potential antifungal applications. This review also assesses and comments on the challenges, shortcomings, and prospect of cationic chitosan derivatives as antifungal therapy.

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Section: Introducing Guanidine Groupsmentioning

confidence: 99%

Cationic chitosan derivatives as potential antifungals: A review of structural optimization and applications

Qin

Guo

2020

Carbohydrate Polymers

127

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“…In order to overcome one or several of the barriers to nonviral transfection to improve gene transfer efficiency, most previous work has focused on physicochemical modifications of the complexing agent [11-14]. Other work has moved beyond the scope of physicochemical vector modifications and placed a focus on the extracellular microenvironment and its role in nonviral gene transfer [15-17], demonstrating that extracellular characteristics such as substrate stiffness, the presence of extracellular matrix (ECM) proteins, and RGD cell adhesion ligand density modulate nonviral gene transfer [18,19].…”

Section: Introductionmentioning

confidence: 99%

The role of surface chemistry-induced cell characteristics on nonviral gene delivery to mouse fibroblasts

Kasputis

Pannier

2012

J Biol Eng

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BackgroundGene delivery approaches serve as a platform to modify gene expression of a cell population with applications including functional genomics, tissue engineering, and gene therapy. The delivery of exogenous genetic material via nonviral vectors has proven to be less toxic and to cause less of an immune response in comparison to viral vectors, but with decreased efficiency of gene transfer. Attempts have been made to improve nonviral gene transfer efficiency by modifying physicochemical properties of gene delivery vectors as well as developing new delivery techniques. In order to further improve and understand nonviral gene delivery, our approach focuses on the cell-material interface, since materials are known to modulate cell behavior, potentially rendering cells more responsive to nonviral gene transfer. In this study, self-assembled monolayers of alkanethiols on gold were employed as model biomaterial interfaces with varying surface chemistries. NIH/3T3 mouse fibroblasts were seeded on the modified surfaces and transfected using either lipid- or polymer- based complexing agents.ResultsTransfection was increased in cells on charged hydrophilic surfaces presenting carboxylic acid terminal functional groups, while cells on uncharged hydrophobic surfaces presenting methyl terminations demonstrated reduced transfection for both complexing agents. Surface–induced cellular characteristics that were hypothesized to affect nonviral gene transfer were subsequently investigated. Cells on charged hydrophilic surfaces presented higher cell densities, more cell spreading, more cells with ellipsoid morphologies, and increased quantities of focal adhesions and cytoskeleton features within cells, in contrast to cell on uncharged hydrophobic surfaces, and these cell behaviors were subsequently correlated to transfection characteristics.ConclusionsExtracellular influences on nonviral gene delivery were investigated by evaluating the upregulation and downregulation of transgene expression as a function of the cell behaviors induced by changes in the cells’ microenvronments. This study demonstrates that simple surface modifications can lead to changes in the efficiency of nonviral gene delivery. In addition, statistically significant differences in various surface-induced cell characteristics were statistically correlated to transfection trends in fibroblasts using both lipid and polymer mediated DNA delivery approaches. The correlations between the evaluated complexing agents and cell behaviors (cell density, spreading, shape, cytoskeleton, focal adhesions, and viability) suggest that polymer-mediated transfection is correlated to cell morphological traits while lipid-mediated transfection correlates to proliferative characteristics.

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“…The results of flow cytometry indicated that guanidinylation promoted an eightfold increase in the cell uptake. The study revealed that guanidinylated chitosan is a promising candidate as an effective nonviral vector for in vivo gene delivery [18]. It was confirmed later that guanidinylation of chitosan could Fig.1.…”

Section: Introductionmentioning

confidence: 73%

Reactions of thiourea oxides with amines, aminoacids and proteins

Makarov¹,

Naidenko²,

Pokrovskaya³

2019

Proceedings of the 1st International Symposium Innovations in Life Sciences (ISILS 2019)

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Guanidinylation: A simple way to fabricate cell penetrating peptide analogue‐modified chitosan vector for enhanced gene delivery

Cited by 38 publications

References 57 publications

Cationic chitosan derivatives as potential antifungals: A review of structural optimization and applications

Cationic chitosan derivatives as potential antifungals: A review of structural optimization and applications

The role of surface chemistry-induced cell characteristics on nonviral gene delivery to mouse fibroblasts

Reactions of thiourea oxides with amines, aminoacids and proteins

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