Synthesis and Immunological Comparison of Differently Linked Lipoarabinomannan Oligosaccharide–Monophosphoryl Lipid A Conjugates as Antituberculosis Vaccines

Wang, Lizhen; Feng, Shaojie; Wang, Subo; Li, Hui; Guo, Zhongwu; Gu, Guofeng

doi:10.1021/acs.joc.7b01817

Cited by 40 publications

(36 citation statements)

References 75 publications

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“…In the aforementioned MPLA based vaccine designs, the antigens were all conjugated with MPLA through 1-O-position instead of 6 ′ -O-position where the polysaccharide chain is attached to LPS in nature (Wang et al, 2017). Guo and Gu further studied the influence of different antigen linkage positions on immunological properties (Schemes 2B,C), by linking a tetrasaccharide antigen from lipoarabinomannan (LAM), a Mycobacterium tuberculosis cell surface lipopolysaccharide, to either 1 or 6 ′ position of MPLA.…”

Section: Mplamentioning

confidence: 99%

Carbohydrate Conjugates in Vaccine Developments

Lang

Huang

2020

Front. Chem.

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Vaccines are powerful tools that can activate the immune system for protection against various diseases. As carbohydrates can play important roles in immune recognition, they have been widely applied in vaccine development. Carbohydrate antigens have been investigated in vaccines against various pathogenic microbes and cancer. Polysaccharides such as dextran and β-glucan can serve as smart vaccine carriers for efficient antigen delivery to immune cells. Some glycolipids, such as galactosylceramide and monophosphoryl lipid A, are strong immune stimulators, which have been studied as vaccine adjuvants. In this review, we focus on the current advances in applying carbohydrates as vaccine delivery carriers and adjuvants. We will discuss the examples that involve chemical modifications of the carbohydrates for effective antigen delivery, as well as covalent antigen-carbohydrate conjugates for enhanced immune responses.

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Section: Mplamentioning

confidence: 99%

Carbohydrate Conjugates in Vaccine Developments

Lang

Huang

2020

Front. Chem.

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“…Lipoarabinomannan (LAM) and related arabinogalactan (AG) are two major structural components of the M. tuberculosis cell wall. Previous studies revealed that LAM and especially its terminal oligosaccharide fragments, conjugated with proteins [7,10,19] or monophosphoryl lipid A [23], are attractive targets for the development of carbohydrate-based anti-TB vaccines [7,10,19,23,65,66].…”

Section: Tuberculosis (Tb) Which Is Caused By the Pathogenic Bacterimentioning

confidence: 99%

“…Some bacterial glycans [1,2] are specific markers for detection and serological identification of microorganisms [3][4][5] and are widely used as antigenic components of vaccines [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23]. The use of gold nanoparticles (GNPs) [24][25][26] as carriers for glyco-epitopes is becoming an important alternative [15, to the traditional conjugation with proteins, synthetic polymers and other carriers [15,17,38,[49][50][51][52][53][54][55].…”

Section: Introductionmentioning

confidence: 99%

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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“…A number of bacterial glycans [1,2] are specific markers for the detection and the serological identification of microorganisms [3][4][5] and are widely used as antigenic components of vaccines [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23]. The use of gold nanoparticles (GNPs) [24][25][26] as carriers for glyco-epitopes is becoming an important alternative [15, to the traditional conjugation with proteins, synthetic polymers and other carriers [15,17,38,[49][50][51][52][53][54][55].…”

Section: Introductionmentioning

confidence: 99%

“…Lipoarabinomannan (LAM) and the related arabinogalactan (AG) are two major structural components of the M. tuberculosis cell wall. Previous studies revealed that LAM and especially its terminal oligosaccharide fragments, conjugated with proteins [7,10,19] or monophosphoryl lipid A [23], are attractive targets for the development of carbohydrate-based anti-TB vaccines [7,10,19,23,65,66].…”

Section: Introductionmentioning

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.

show abstract

Synthesis and Immunological Comparison of Differently Linked Lipoarabinomannan Oligosaccharide–Monophosphoryl Lipid A Conjugates as Antituberculosis Vaccines

Cited by 40 publications

References 75 publications

Carbohydrate Conjugates in Vaccine Developments

Carbohydrate Conjugates in Vaccine Developments

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

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