Nano-caged shikimate as a multi-site cross-linker of collagen for biomedical applications

Srivatsan, Kunnavakkam Vinjimur; Duraipandy, Natarajan; Lakra, Rachita; Sandhiya, K; Ramamurthy, Usha; Korrapati, Purna Sai; Kiran, Manikantan Syamala

doi:10.1039/c5ra02278a

Cited by 8 publications

(6 citation statements)

References 56 publications

(56 reference statements)

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“…Shikimic acid has also found its use in material science as an additive in the stabilization of metal nanoparticles and cross-link collagen for use in tissue engineering applications . Banach and Pulit-Prociak prepared a series of metal nanoparticles by chemical reduction with tannic and shikimic acids, sodium salicylate, or sodium potassium tartrate as reducing and stabilizing agents.…”

Section: Miscellaneous Applications Of Shikimic Acidmentioning

confidence: 99%

“…Additionally, shikimic acid caged silver nanoparticle stabilized collagen showed cell proliferative and antimicrobial properties. Surprisingly, even though shikimic acid is engineered and produced in E. coli , its conjugation with silver nanoparticles resulted in microbial growth inhibition …”

Section: Miscellaneous Applications Of Shikimic Acidmentioning

confidence: 99%

“…339 Shikimic acid has also found its use in material science as an additive in the stabilization of metal nanoparticles 446 and crosslink collagen for use in tissue engineering applications. 447 Banach and Pulit-Prociak prepared a series of metal nanoparticles by chemical reduction with tannic and shikimic acids, sodium salicylate, or sodium potassium tartrate as reducing and stabilizing agents. The stabilizing properties of shikimic acid in the silver nanoparticles resulted in fabrication of nanoparticles in 90−105 nm size, while smaller gold nanoparticles were obtained in 60−80 nm sizes.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Production and Synthetic Modifications of Shikimic Acid

2018

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Shikimic acid is a natural product of industrial importance utilized as a precursor of the antiviral Tamiflu. It is nowadays produced in multihundred ton amounts from the extraction of star anise (Illicium verum) or by fermentation processes. Apart from the production of Tamiflu, shikimic acid has gathered particular notoriety as its useful carbon backbone and inherent chirality provide extensive use as a versatile chiral precursor in organic synthesis. This review provides an overview of the main synthetic and microbial methods for production of shikimic acid and highlights selected methods for isolation from available plant sources. Furthermore, we have attempted to demonstrate the synthetic utility of shikimic acid by covering the most important synthetic modifications and related applications, namely, synthesis of Tamiflu and derivatives, synthetic manipulations of the main functional groups, and its use as biorenewable material and in total synthesis. Given its rich chemistry and availability, shikimic acid is undoubtedly a promising platform molecule for further exploration. Therefore, in the end, we outline some challenges and promising future directions.

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Section: Miscellaneous Applications Of Shikimic Acidmentioning

confidence: 99%

Section: Miscellaneous Applications Of Shikimic Acidmentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%

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Production and Synthetic Modifications of Shikimic Acid

2018

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“…However, once the concentration of AgNPs exceeded the critical point (i.e., the A/P ratio exceeded 1 : 10), the crash between AgNPs increased rapidly, which offset the dispersive power and the protection of the EPS to AgNPs. 31,32 The band at 1000-1200 cm À1 was attributed to the C-O antisymmetric stretching in the C-O-H and C-O-C groups of polysaccharides. 30 The FT-IR could provide the information about the interactions between molecules.…”

Section: Synthesis Of Agnpsmentioning

confidence: 99%

“…The broad peak at 3300-3450 cm À1 was assigned to the stretching vibrations of O-H and a weak peak at 2924 cm À1 was an indication of the C-H stretching vibrations of polysaccharide. 31,32 The band at 1000-1200 cm À1 was attributed to the C-O antisymmetric stretching in the C-O-H and C-O-C groups of polysaccharides. 33,34 It can be clearly observed that the characteristic absorption peak of OH for the pure EPS was at 3439 cm À1 , while those for the EPS-Ag nanocomposites were in a higher wavenumber range (3450-3462 cm À1 ).…”

Section: Synthesis Of Agnpsmentioning

confidence: 99%

In situ synthesis of silver nanoparticles dispersed or wrapped by a Cordyceps sinensis exopolysaccharide in water and their catalytic activity

et al. 2015

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Well-dispersed Ag nanoparticles (AgNPs) were constructed via in situ reduction of Ag + under the macromolecular environment of a Cordyceps sinensis exopolysaccharide (EPS). The EPS-Ag nanocomposites were characterized in terms of formation, size, morphology, and Ag distribution by UV-VIS, FT-IR, laser light scattering measurements, transmission electron microscopy (TEM), energy dispersive X-ray (EDX) and X-ray photoelectron spectroscopy (XPS). Results indicated that the AgNPs in the EPS microenvironment were present in two forms: 99% of small-sized AgNPs ($5.0 nm in diameter) uniformly dispersed by single-molecular EPS and 1% of aggregated EPS-Ag nanocomposites ($300 nm in diameter). The interactions between the OH groups of the EPS and AgNPs (C-O-Ag bonds) substituted for inter-and intra-molecular interactions in native EPS, leading to good dispersion of AgNPs in the EPS matrix. Meanwhile, only a few EPS aggregates wrapped many small-sized AgNPs to form large-sized EPS-Ag nanocomposites through strong physical adsorption to O atoms of other EPS aggregates on the surfaces of AgNPs. Additionally, the introduction of dimethyl sulfoxide (DMSO) would facilitate the aggregation of AgNPs in the aqueous system. This work not only provides a simple and efficient approach to construct well-dispersed AgNPs in the aqueous system, and demonstrates the crucial role of the EPS as a biopolymer template for dispersion, stabilization and size control of AgNPs, but also finds the EPS-Ag nanocomposites can serve as a good catalyst for the reduction of 4nitrophenol to 4-aminophenol by NaBH 4 . The catalytic reduction had a pseudo-first-order rate constant of 1.26 Â 10 À3 s À1 and an activity parameter of 15.75 s À1 g À1 .

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Lanthanum oxide nanoparticle-collagen bio matrix induced endothelial cell activation for sustained angiogenic response for biomaterial integration

Vijayan

Lakra

Korrapati

et al. 2022

Colloids and Surfaces B: Biointerfaces

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Nano-caged shikimate as a multi-site cross-linker of collagen for biomedical applications

Abstract: Shikimic acid caged silver nanoparticles as multi-site cross-linkers of collagen for tissue engineering applications.

Cited by 8 publications

References 56 publications

Production and Synthetic Modifications of Shikimic Acid

Production and Synthetic Modifications of Shikimic Acid

In situ synthesis of silver nanoparticles dispersed or wrapped by a Cordyceps sinensis exopolysaccharide in water and their catalytic activity

Lanthanum oxide nanoparticle-collagen bio matrix induced endothelial cell activation for sustained angiogenic response for biomaterial integration

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