Carbohydrate functionalized iron(iii) complexes as biomimetic siderophores

Yadav, Rohan; Kikkeri, Raghavendra

doi:10.1039/c2cc16656a

Cited by 22 publications

(14 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To address the biological significance of glyco‐AuNPs, their binding affinity to ConA lectin was established . We performed inhibition studies for the binding of these lectins to mannose–BSA in the presence of homo‐ and hetero‐glyco‐AuNPs and quantitation was reported as the IC 50 value (Table and Figure S2).…”

Section: Resultsmentioning

confidence: 99%

Exploring the Influence of Shapes and Heterogeneity of Glyco‐Gold Nanoparticles on Bacterial Binding for Preventing Infections

et al. 2017

Self Cite

View full text Add to dashboard Cite

To investigate the effects of the heterogeneity and shape of glyco-nanoprobes on carbohydrate-protein interactions (CPIs), α-d-mannose- and β-d-galactose-linked homo- and heterogeneous glycodendrons were synthesized and immobilized on spherical and rod-shaped gold nanoparticles (AuNPs). Lectin and bacterial binding studies of these glyco-AuNPs clearly illustrate that multivalency and shape of AuNPs contribute significantly to CPIs than the heterogeneity of glycodendrons. Finally, bacterial infection of HeLa cells was effectively inhibited by the homogeneous glycodendron-conjugated rod-shaped AuNPs relative to their heterogeneous counterparts. Overall, these results provide insight into the role of AuNP shape and multivalency as potential factors to regulate CPIs.

show abstract

Section: Resultsmentioning

confidence: 99%

Exploring the Influence of Shapes and Heterogeneity of Glyco‐Gold Nanoparticles on Bacterial Binding for Preventing Infections

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…Pipyridyl‐glycoclusters functionalized with the Tn‐antigen (α‐GalNAc‐OR) were used for the formation of copper(II) complexes with enhanced binding to Vicia villo lectin (R. Roy & Kim, ). Similarly, a catechol‐functionalized iron(III) glycodendrimer better targeted Escherichia coli ORN78 and was used as an iron delivery carrier (Yadav & Kikkeri, ). Saccharide‐coated M 12 L 24 complexes based on Pd(II) (Y. Liu, Zhang, et al, ) showed potential in Alzheimer diagnosis (Sato et al, ; Yan et al, ).…”

Section: Oligosaccharidesmentioning

confidence: 99%

Carbohydrate‐based nanomaterials for biomedical applications

Gim

Zhu

Seeberger

et al. 2019

WIREs Nanomed Nanobiotechnol

View full text Add to dashboard Cite

Carbohydrates are abundant biomolecules, with a strong tendency to form supramolecular networks. A host of carbohydrate-based nanomaterials have been exploited for biomedical applications. These structures are based on simple monoor disaccharides, as well as on complex, polymeric systems. Chemical modifications serve to tune the shapes and properties of these materials. In particular, carbohydrate-based nanoparticles and nanogels were used for drug delivery, imaging, and tissue engineering applications. Due to the reversible nature of the assembly, often based on a combination of hydrogen bonding and hydrophobic interactions, carbohydrate-based materials are valuable substrates for the creations of responsive systems. Herein, we review the current research on carbohydratebased nanomaterials, with a particular focus on carbohydrate assembly. We will discuss how these systems are formed and how their properties are tuned. Particular emphasis will be placed on the use of carbohydrates for biomedical applications.

show abstract

“…To illustrate the first point, abundant examples are available in nature in the form of siderophores such as enterobactin, bacillibactin, and vibriobactin. [26][27][28] Since Fe 3 + is a hard Lewis acidic center, it prefers hard donors such as oxide ions for stabilization. Again, generation of the lowenergy LCMT band in Fe III -catecholate complexes is well documented in the literature.…”

Section: Synthesis and General Aspectsmentioning

confidence: 99%

Iron(III) Catecholates for Cellular Imaging and Photocytotoxicity in Red Light

Basu

Pant

Khan

et al. 2014

Chemistry An Asian Journal

View full text Add to dashboard Cite

Iron(III) complexes [Fe(L)(L')(NO3)]--in which L is phenyl-N,N-bis[(pyridin-2-yl)methyl]methanamine (1), (anthracen-9-yl)-N,N-bis[(pyridin-2-yl)methyl]methanamine (2), (pyreny-1-yl)-N,N-bis[(pyridin-2-yl)methyl]methanamine (3-5), and L' is catecholate (1-3), 4-tert-butyl catecholate (4), and 4-(2-aminoethyl)-benzene-1,2-diolate (5)--were synthesized and their photocytotoxic properties examined. The five electron-paramagnetic complexes displayed a Fe(III)/Fe(II) redox couple near -0.4 V versus a saturated calomel electrode (SCE) in DMF/0.1 M tetrabutylammonium perchlorate (TBAP). They showed unprecedented photocytotoxicity in red light (600-720 nm) to give IC50≈15 μM in various cell lines by means of apoptosis to generate reactive oxygen species. They were ingested in the nucleus of HeLa and HaCaT cells in 4 h, thereby interacting favorably with calf thymus (ct)-DNA and photocleaving pUC19 DNA in red light of 785 nm to form hydroxyl radicals.

show abstract

Carbohydrate functionalized iron(iii) complexes as biomimetic siderophores

Abstract: Catechol functionalized iron(III) glycodendrimers have been prepared using a self-assembly process for targeting a specific strain of E. coli bacteria and have been shown to exhibit carbohydrate-lectin mediated iron delivery in growth promotion assay.

Cited by 22 publications

References 27 publications

Exploring the Influence of Shapes and Heterogeneity of Glyco‐Gold Nanoparticles on Bacterial Binding for Preventing Infections

Exploring the Influence of Shapes and Heterogeneity of Glyco‐Gold Nanoparticles on Bacterial Binding for Preventing Infections

Carbohydrate‐based nanomaterials for biomedical applications

Iron(III) Catecholates for Cellular Imaging and Photocytotoxicity in Red Light

Contact Info

Product

Resources

About