Polarimetry as a Tool for the Study of Solutions of Chiral Solutes

Orlova, A. V.; Andrade, Renato R.; Silva, Clarissa O. da; Zinin, Alexander I.; Kononov, L. O.

doi:10.1002/cphc.201300894

Cited by 32 publications

(33 citation statements)

References 68 publications

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“…The observed differences in specificity of antibodies generated against the two sets We have recently argued [103][104][105] that the sometimes observed profound influence of the nature of (functionalized) aglycon in a glycosyl acceptor may be related to formation of reaction solutions with modified structure that are featured by the presence of different supramolecular assemblies of reagents (supramers [102]) in solution. In a similar fashion, solutions of Ara6C2NH2-GNPs 3 with shorter and more hydrophobic С2 spacer aglycon might form more dense [106,107] supramers in aqueous solutions [102,[108][109][110] which eventually would form more clustered Ara6glycan domains on the surface of Ara6-GNPs.…”

Section: Discussionmentioning

confidence: 93%

Preparation of glyco-gold nanoparticles carrying synthetic mycobacterial hexaarabinofuranoside and their evaluation in vivo

Burygin¹,

Abronina²,

Podvalnyy³

et al. 2019

Preprint

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Some bacterial glycans are specific markers for detection and serological identification of microorganisms and are widely used as antigenic components of vaccines. The use of gold nanoparticles as carriers for glyco-epitopes is becoming an important alternative to the traditional conjugation with proteins and synthetic polymers. In this study, we aimed at preparation and evaluation in vivo of glyco-gold nanoparticles (glyco-GNPs) bearing the terminal branched hexaarabinofuranoside fragment (Ara6) of arabinan domains of lipoarabinomannan and arabinogalactan, which are principal polysaccharides of the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. Specifically, we were interested in checking if the antibodies generated against Ara6-GNPs would recognize the natural saccharides on the cell surface of different mycobacterial strains. Two synthetic Ara6 glycosides with amino-functionalized spacer aglycons differing in length and hydrophilicity were directly conjugated with spherical gold nanoparticles (d = 15 nm) to give two sets of glyco-GNPs which were used for immunization of rabbits. Dot assay revealed cross-reactions for the two obtained antisera with the hexaarabinofuranoside with 2-aminoethyl aglycon used for the preparation of glyco-GNPs. Both antisera contained high titers of antibodies specific for Mycobacteria as shown by enzyme-linked immunosorbent assay using M. bovis and M. smegmatis cells as antigens while gave a weak response with M. phlei cells and no interaction with E. coli cells. The results obtained suggest that glyco-GNPs are promising agents for generation of anti-mycobacterial antibodies.

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Section: Discussionmentioning

confidence: 93%

Preparation of glyco-gold nanoparticles carrying synthetic mycobacterial hexaarabinofuranoside and their evaluation in vivo

Burygin¹,

Abronina²,

Podvalnyy³

et al. 2019

Preprint

View full text Add to dashboard Cite

show abstract

“…We have recently argued [105][106][107] that the sometimes observed profound influence of the nature of the (functionalized) aglycon in a glycosyl acceptor may be related to the formation of reaction solutions with modified structures featuring different supramolecular assemblies of the reagents (supramers [104]) in solution. In a similar fashion, solutions of Ara 6 C 2 NH 2 -GNPs 3 with the shorter and more hydrophobic С 2 spacer aglycon might form tighter [108][109][110] supramers in aqueous solution [104,111,112], which eventually would form more clustered Ara 6 -glycan domains on the surface of Ara 6 -GNPs. The results obtained clearly suggest that the choice of the spacer aglycon may be critical for the specificity of antibodies against the corresponding glyco-GNPs and the studies in this direction seem promising.…”

Section: Discussionmentioning

confidence: 99%

Preparation and in vivo evaluation of glyco-gold nanoparticles carrying synthetic mycobacterial hexaarabinofuranoside

Burygin¹,

Abronina²,

Podvalnyy³

et al. 2020

Beilstein J. Nanotechnol.

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A number of bacterial glycans are specific markers for the detection and the serological identification of microorganisms and are also widely used as antigenic components of vaccines. The use of gold nanoparticles as carriers for glyco-epitopes is becoming an important alternative to the traditional conjugation with proteins and synthetic polymers. In this study, we aimed to prepare and evaluate in vivo glyco-gold nanoparticles (glyco-GNPs) bearing the terminal-branched hexaarabinofuranoside fragment (Ara6) of arabinan domains of lipoarabinomannan and arabinogalactan, which are principal polysaccharides of the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. In particular, we were interested whether the antibodies generated against Ara6-GNPs would recognize the natural saccharides on the cell surface of different mycobacterial strains. Two synthetic Ara6 glycosides with amino-functionalized spacer aglycons differing in length and hydrophilicity were directly conjugated with spherical gold nanoparticles (d = 15 nm) to give two sets of glyco-GNPs, which were used for the immunization of rabbits. Dot assays revealed cross-reactions between the two obtained antisera with the hexaarabinofuranoside and the 2-aminoethyl aglycon used for the preparation of glyco-GNPs. Both antisera contained high titers of antibodies specific for Mycobacteria as shown by enzyme-linked immunosorbent assay using M. bovis and M. smegmatis cells as antigens while there was only a weak response to M. phlei cells and no interaction with E. coli cells. The results obtained suggest that glyco-GNPs are promising agents for the generation of anti-mycobacterial antibodies.

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“…Compounds 1 and 2 were prepared and purified according to the described procedures [34,35]. Ultrapure water with a resistivity of >18 MΩ•cm (OMNI-A water purification system (PRC), using distilled water as the source) was used for preparation of aqueous solutions and chromatography.…”

Section: Methodsmentioning

confidence: 99%

“…If these changes depend on the concentration, they are usually thought to be associated with aggregation of solute molecules [32]. Therefore, it can be expected that supramers consisting of molecules in a different conformation or differing in the way they are packed [33] or solvated [34], will also differ in the values of specific rotation.…”

Section: Introductionmentioning

confidence: 99%

Polarimetry as a method for studying the structure of aqueous carbohydrate solutions: correlation with other methods

Orlova¹,

Kononov²

2020

RENSIT

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The review provides data indicating that polarimetry is a sensitive tool for studying the structure of aqueous carbohydrate solutions. Using aqueous solutions of D-levoglucosan (1,6-anhydro-D-glucopyranose) as an example, it was demonstrated, using polarimetry, quantum chemical calculations, HPLC, static and dynamic light scattering, that polarimetry allows one to detect changes in the structure of solutions with changes in concentration and temperature, as well as the evolution of the structure of solutions over time. In particular, the phenomenon of the existence of "critical" concentrations and temperatures was discovered at which the specific rotation of the solutions undergo jump-like changes, apparently reflecting rearrangements in the structure of the solution. It is also possible that in the case of aqueous solutions, chiral carbohydrate molecules might act as "probes" that "sense" the slightest changes in their conformation or rearrangement of the environment (in the solvation shell) caused by changes in the structure of water, which at the macroscopic level manifests themselves as change in specific rotation.

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Polarimetry as a Tool for the Study of Solutions of Chiral Solutes

Cited by 32 publications

References 68 publications

Preparation of glyco-gold nanoparticles carrying synthetic mycobacterial hexaarabinofuranoside and their evaluation in vivo

Preparation of glyco-gold nanoparticles carrying synthetic mycobacterial hexaarabinofuranoside and their evaluation in vivo

Preparation and in vivo evaluation of glyco-gold nanoparticles carrying synthetic mycobacterial hexaarabinofuranoside

Polarimetry as a method for studying the structure of aqueous carbohydrate solutions: correlation with other methods

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