A new synthetic methodology for pyridinic sucrose esters and their antibacterial effects against Gram-positive and Gram-negative strains

Vargas, Jorge Andrés Mora; Ortega, Julieth Orduña; Santos, Maitê Bernardo Correia dos; Metzker, Gustavo; Gomes, Eleni; Boscolo, Maurício

doi:10.1016/j.carres.2020.107957

Carbohydrate Research

2020

DOI: 10.1016/j.carres.2020.107957

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A new synthetic methodology for pyridinic sucrose esters and their antibacterial effects against Gram-positive and Gram-negative strains

Jorge Andrés Mora Vargas

Julieth Orduña Ortega

Maitê Bernardo Correia dos Santos

et al.

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Cited by 9 publications

(1 citation statement)

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“…8 To form self-assemblies in the aqueous phase for gene delivery, hydrophobic groups have been introduced into the structure of carbohydrates. However, during the hydrophobic modification processes, including the esterification of sucrose, complex mixtures are often produced because of polyreactive sites of carbohydrates, 9 thus limiting the application of hydrophobic carbohydrates in gene delivery studies.…”

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Biodegradable Sucrose Ester-Based Cationic Lipids as Novel Vectors for Efficient and Safe Delivery of IGF-1R siRNA

Zhi

Shi

Cui

et al. 2023

ACS Materials Lett.

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The key to the success of siRNA therapy depends on the use of siRNA delivery agents that effectively penetrate tumor cells and simultaneously protect siRNA from RNase attacks. Sucrose esters (SEs) are found to have tremendous potential applications in siRNA delivery because of their biocompatibility and low toxicity. However, the esterification of sucrose yields complex mixtures that greatly limit their progress in this field. We synthesized a series of novel sucrose monoester-based cationic lipids (SECLs) by using 1′,4,6′-trichlorogalactosucrose (TGS) to achieve monoesterification of sucrose. SECL-based liposomes formed from these lipids and colipids [dioleoylphosphatidylethanolamine (DOPE) or cholesterol (Chol)] could effectively condense genes into nanocomplexes, which exhibited significantly higher uptake rates and gene silencing efficiency than 1,2-dioleoyl-3-trimethylammonium-propane (DOTAP) liposome. Furthermore, SECL-based liposomes containing cholesterol-mediated IGF-1R siRNA delivery could inhibit tumor growth by the downregulation of Bcl-2 and the upregulation of Bax. Most importantly, these liposomes displayed low cytotoxicity in vitro and in vivo because they could be degraded under tumor acidic pH environments. Our study establishes a novel method for the synthesis of SEs from TGS and demonstrates the applicability of SECLs for gene delivery with the potential for clinical therapy.

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confidence: 99%

Biodegradable Sucrose Ester-Based Cationic Lipids as Novel Vectors for Efficient and Safe Delivery of IGF-1R siRNA

Zhi

Shi

Cui

et al. 2023

ACS Materials Lett.

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Sucrose and Glycerol Additives: A Way to Tune the Biological and Physicochemical Properties of Agarose Hydrogels?

Igbokwe,

Ball,

Benzaamia

et al. 2024

Macro Materials & Eng

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Sucrose and glycerol have gained attention as additives for hydrogels, owing to their capacity to exert considerable influence over the physicochemical, mechanical, and biological characteristics of these materials. Herein, these effects on agarose hydrogels (AHs) are explored. A series of AHs are synthesized using sucrose (30% and 300% w/v) and glycerol as additives. The storage modulus (10.0–13.7 kPa) and hydrophilicity of the hydrogels (contact angle < 50°) do not vary significantly with sucrose or glycerol addition. However, sucrose enhances the hydration capacity of the hydrogels by up to 170%, whereas glycerol reduces it. Interestingly, sucrose and glycerol individually do not have bacteriostatic effects against Staphylococcus epidermidis, but their combination significantly (p ≤ 0.001) inhibits the growth of both S. epidermidis and Pseudomonas aeruginosa by 63% and 29%, respectively, in comparison to native agarose. Cytotoxicity testing on NIH/3T3 murine fibroblasts reveals that sucrose increases cell viability up to 98%, while glycerol reduces it below 60%. Overall, these hydrogels hold promise for antibacterial biomedical applications as wound dressing materials and surface coatings for medical devices and can also be used to formulate bioinks for 3D bioprinting.

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Antimicrobial activity and structure–activity relationships of molecules containing mono- or di- or oligosaccharides: An update

Zhou,

Hao,

Tang

et al. 2024

Bioorganic Chemistry

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A new synthetic methodology for pyridinic sucrose esters and their antibacterial effects against Gram-positive and Gram-negative strains

Cited by 9 publications

References 40 publications

Biodegradable Sucrose Ester-Based Cationic Lipids as Novel Vectors for Efficient and Safe Delivery of IGF-1R siRNA

Biodegradable Sucrose Ester-Based Cationic Lipids as Novel Vectors for Efficient and Safe Delivery of IGF-1R siRNA

Sucrose and Glycerol Additives: A Way to Tune the Biological and Physicochemical Properties of Agarose Hydrogels?

Antimicrobial activity and structure–activity relationships of molecules containing mono- or di- or oligosaccharides: An update

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