Enzymatic synthesis and self-assembly of glycolipids: robust self-healing and wound closure performance of assembled soft materials

Prasad, Yadavali Siva; Saritha, B.; Tamizhanban, Ayyapillai; Lalitha, Krishnamoorthy; Sakthivel, Kabilan; Maheswari, C. Uma; Sridharan, Vellaisamy; Nagarajan, Subbiah

doi:10.1039/c8ra07703g

Cited by 14 publications

(32 citation statements)

References 82 publications

(90 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…439 Glycolipids were produced using α-chloralose and various vinyl esters as substrates and N435 as a catalyst. 440 In other cases, oils and simple free fatty acid esters have been used. For instance, medium and long chain triacylglycerols were synthesized in a solvent-free system by interesterification of soybean oil with medium chain esters using N435 as a catalyst.…”

Section: Food Technology: Glyceride Modifications and Productionmentioning

confidence: 99%

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Ortíz

Ferreira

Barbosa

et al. 2019

Catal. Sci. Technol.

422

343

View full text Add to dashboard Cite

show abstract

Section: Food Technology: Glyceride Modifications and Productionmentioning

confidence: 99%

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Ortíz

Ferreira

Barbosa

et al. 2019

Catal. Sci. Technol.

422

343

View full text Add to dashboard Cite

show abstract

“…The progress of the reactions was monitored by thinlayer chromatography (TLC) on pre-coated silica gel plates purchased from Merck and visualized by UV detection or using sulfuric acid spray or molecular iodine. Column chromatography was performed on Silica Gel (100-200 mesh) purchased from Avra chemicals, India 38 .…”

Section: Methodsmentioning

confidence: 99%

“…The unbound CV was removed by rinsing thrice with 200 μL of PBS. Further, 70% ethanol was added and incubated for 15 min to destain the CV and the absorbance of each well was measured at 595 nm using the microplate reader as a proxy for the biomass 38 .…”

Section: Methodsmentioning

confidence: 99%

“…In this line, there is a great demand in the construction of multifunctional self-assembled gel-based materials for biomedical application, especially diabetic wound closure and infection management. In our previous report, we have developed an oleogel and composite gel from α-chloralose, a carbohydrate based molecule displaying long lasting anesthetic property 37 , which displayed good viscoelastic properties by molecular self-assembly of glycolipidand excellent wound healing activity in normal Wistar rat models 38 . In continuation of our previous work with promising results, we were curious to examine the wound closure behaviour of our self-assembled low molecular weight gels towards diabetic wounds and explore the antibiofilm property of sugar derived self-assembled gels [39][40][41] .…”

mentioning

confidence: 99%

See 1 more Smart Citation

An injectable self-healing anesthetic glycolipid-based oleogel with antibiofilm and diabetic wound skin repair properties

Prasad

Miryala

Lalitha

et al. 2020

Sci Rep

Self Cite

View full text Add to dashboard Cite

Globally, wound infections are considered as one of the major healthcare problems owing to the delayed healing process in diabetic patients and microbial contamination. Thus, the development of advanced materials for wound skin repair is of great research interest. Even though several biomaterials were identified as wound healing agents, gel-based scaffolds derived from either polymer or small molecules have displayed promising wound closure mechanism. Herein, for the first time, we report an injectable and self-healing self-assembled anesthetic oleogel derived from glycolipid, which exhibits antibiofilm and wound closure performance in diabetic rat. Glycolipid derived by the reaction of hydrophobic vinyl ester with α-chloralose in the presence of novozyme 435 undergoes spontaneous self-assembly in paraffin oil furnished an oleogel displaying self-healing behavior. In addition, we have prepared composite gel by encapsulating curcumin in the 3D fibrous network of oleogel. More interestingly, glycolipid in its native form demoed potential in disassembling methicillin-resistant Staphylococcus aureus, methicillin-susceptible Staphylococcus aureus, and Pseudomonas aeruginosa biofilms. Both oleogel and composite gel enhanced the wound skin repair in diabetic induced Wistar rats by promoting collagen synthesis, controlling free radical generation and further regulating tissue remodeling phases. Altogether, the reported supramolecular self-assembled anesthetic glycolipid could be potentially used for diabetic skin wound repair and to treat bacterial biofilm related infections.

show abstract

“…Gelation ability of gluconamide-based amphiphiles 4a and 4b were determined by the "stable to inversion" method. [56,58,59,81] A large range of organic solvents and edible vegetable oils were used for the gelation test. The minimum gelation concentration (MGC) of gelator in % w/v (i.e., mg/100 µL) was identified by taking a known quantity of gelator in a vial followed by the addition of an appropriate amount of solvent/oil.…”

Section: Gelation Studiesmentioning

confidence: 99%

Supramolecular gels of gluconamides derived from renewable resources: Antibacterial and anti‐biofilm applications

et al. 2020

Self Cite

View full text Add to dashboard Cite

Carbohydrates are versatile materials widely used for several applications including food, pharmaceuticals, cosmetics, and drug delivery systems due to their inherent properties such as non-toxicity, biodegradability, and bio-compatibility. Specifically, the urge on carbohydrate research is due to its significance in the biological system, for example, a glycoprotein found in the extracellular matrix, involved in signaling pathways, cell-cell interaction and cell-matrix interaction. Because of the increase in demand of glycolipids for biological applications, in this report, a set of three structurally related gluconamide-based amphiphiles were synthesized from renewable resources, δ-gluconolactone and cashew nut shell liquid. The molecular structure of the synthesized glycolipids was characterized by NMR and mass spectral techniques. Molecular self-assembly of gluconamide-based amphiphiles was investigated relative to the molecular structure and nature of the solvent used. Interestingly, the nature of the hydrophobic tail present in the glycolipids influences the self-assembly pattern, which results in a hydrogel, organogel and highly insoluble nanorods. Gelation studies clearly revealed that the involvement of different magnitude of non-covalent interactions such as hydrogen bonding, π-π stacking and van der Waals interaction. Morphology of self-assembled architecture was investigated by optical microscopy, FESEM and FETEM analysis. The mechanism involved in the molecular self-assembly has been deduced by small angle XRD analysis. Thermo reversibility and the thixotropic nature of the derived gels were identified by rheological measurements. Further, antimicrobial and biofilm inhibitory activity of gluconamide-based amphiphiles were studied against various pathogenic bacterial strains Staphylococcus aureus, Listeria monocytogenes, Salmonella This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

show abstract

Enzymatic synthesis and self-assembly of glycolipids: robust self-healing and wound closure performance of assembled soft materials

Abstract: In this report, we present a new class of injectable oleogels and a composite gel derived from glycolipids that provide a reversible interlinked 3D fiberous network architecture for effective wound closure by tissue regrowth and regeneration.

Cited by 14 publications

References 82 publications

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Novozym 435: the “perfect” lipase immobilized biocatalyst?

An injectable self-healing anesthetic glycolipid-based oleogel with antibiofilm and diabetic wound skin repair properties

Supramolecular gels of gluconamides derived from renewable resources: Antibacterial and anti‐biofilm applications

Contact Info

Product

Resources

About