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Article ; Online: Immunotherapy for cancer: synthetic carbohydrate-based vaccines

Buskas, Therese / Thompson, Pamela / Boons, Geert-Jan

Chemical communications. 2009 Sept. 2, no. 36, p. 5335-5349

2009 , Page(s) 5335–5349

Abstract: Aberrant glycosylation of glycoproteins and glycolipids of cancer cells, which correlates with poor survival rates, is being exploited for the development of immunotherapies for cancer. In particular, advances in the knowledge of cooperation between the ... ...

Abstract	Aberrant glycosylation of glycoproteins and glycolipids of cancer cells, which correlates with poor survival rates, is being exploited for the development of immunotherapies for cancer. In particular, advances in the knowledge of cooperation between the innate and adaptive system combined with the implementation of efficient synthetic methods for assembly of oligosaccharides and glycopeptides is providing avenues for the rationale design of vaccine candidates. In this respect, fully synthetic vaccine candidates show great promise because they incorporate only those elements requires for relevant immune responses, and hence do not suffer from immune suppression observed with classical carbohydrate–protein conjugate vaccines. Such vaccines are chemically well-defined and it is to be expected that they can be produced in a reproducible fashion. In this feature article, recent advances in the development of fully synthetic sub-unit carbohydrate-based cancer vaccines will be discussed.
Keywords	cancer vaccines ; chemical communication ; chemical compounds ; glycolipids ; glycopeptides ; glycoproteins ; glycosylation ; immune response ; immunotherapy ; neoplasm cells ; neoplasms ; oligosaccharides ; survival rate ; vaccine development
Language	English
Dates of publication	2009-0902
Size	p. 5335-5349
Publishing place	The Royal Society of Chemistry
Document type	Article ; Online
Note	Use and reproduction
ZDB-ID	1472881-3
ISSN	1364-548X ; 1359-7345 ; 0009-241X
ISSN (online)	1364-548X
ISSN	1359-7345 ; 0009-241X
DOI	10.1039/b908664c
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research.

Boltje, Thomas J / Buskas, Therese / Boons, Geert-Jan

Nature chemistry

2009 Volume 1, Issue 8, Page(s) 611–622

Abstract: Synthetic oligosaccharides and glycoconjugates are increasingly used as probes for biological research and as lead compounds for drug and vaccine discovery. These endeavors are, however, complicated by a lack of general methods for the routine ... ...

Abstract	Synthetic oligosaccharides and glycoconjugates are increasingly used as probes for biological research and as lead compounds for drug and vaccine discovery. These endeavors are, however, complicated by a lack of general methods for the routine preparation of this important class of compounds. Recent development such as one-pot multi-step protecting group manipulations, the use of unified monosaccharide building blocks, the introduction of stereoselective glycosylation protocols, and convergent strategies for oligosaccharide assembly, are beginning to address these problems. Furthermore, oligosaccharide synthesis can be facilitated by chemo-enzymatic methods, which employ a range of glycosyl transferases to modify a synthetic oligosaccharide precursor. Glycosynthases, which are mutant glycosidases, that can readily form glycosidic linkages are addressing a lack of a wide range glycosyltransferases. The power of carbohydrate chemistry is highlighted by an ability to synthesize glycoproteins.
MeSH term(s)	Amino Acid Sequence ; Enzymes/metabolism ; Glycoconjugates/chemical synthesis ; Glycoconjugates/chemistry ; Glycoconjugates/metabolism ; Glycomics ; Glycosylation ; Humans ; Molecular Sequence Data ; Oligosaccharides/chemical synthesis ; Oligosaccharides/chemistry ; Oligosaccharides/metabolism ; Polymers/chemistry
Chemical Substances	Enzymes ; Glycoconjugates ; Oligosaccharides ; Polymers
Language	English
Publishing date	2009-07-20
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Review
ZDB-ID	2464596-5
ISSN	1755-4349 ; 1755-4330
ISSN (online)	1755-4349
ISSN	1755-4330
DOI	10.1038/nchem.399
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Immunotherapy for cancer: synthetic carbohydrate-based vaccines.

Buskas, Therese / Thompson, Pamela / Boons, Geert-Jan

Chemical communications (Cambridge, England)

2009 , Issue 36, Page(s) 5335–5349

Abstract	Aberrant glycosylation of glycoproteins and glycolipids of cancer cells, which correlates with poor survival rates, is being exploited for the development of immunotherapies for cancer. In particular, advances in the knowledge of cooperation between the innate and adaptive system combined with the implementation of efficient synthetic methods for assembly of oligosaccharides and glycopeptides is providing avenues for the rationale design of vaccine candidates. In this respect, fully synthetic vaccine candidates show great promise because they incorporate only those elements requires for relevant immune responses, and hence do not suffer from immune suppression observed with classical carbohydrate-protein conjugate vaccines. Such vaccines are chemically well-defined and it is to be expected that they can be produced in a reproducible fashion. In this feature article, recent advances in the development of fully synthetic sub-unit carbohydrate-based cancer vaccines will be discussed.
MeSH term(s)	Animals ; Antibodies/blood ; Antibodies/immunology ; Antigens, Tumor-Associated, Carbohydrate/chemistry ; Antigens, Tumor-Associated, Carbohydrate/immunology ; Cancer Vaccines/chemical synthesis ; Cancer Vaccines/chemistry ; Cancer Vaccines/immunology ; Carbohydrate Sequence ; Humans ; Molecular Sequence Data ; Neoplasms/chemistry ; Neoplasms/immunology ; Neoplasms/pathology ; Neoplasms/therapy ; Vaccines, Subunit/chemical synthesis ; Vaccines, Subunit/chemistry ; Vaccines, Subunit/immunology ; Vaccines, Synthetic/chemistry ; Vaccines, Synthetic/immunology
Chemical Substances	Antibodies ; Antigens, Tumor-Associated, Carbohydrate ; Cancer Vaccines ; Vaccines, Subunit ; Vaccines, Synthetic
Language	English
Publishing date	2009-07-22
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Review
ZDB-ID	1472881-3
ISSN	1364-548X ; 1359-7345 ; 0009-241X
ISSN (online)	1364-548X
ISSN	1359-7345 ; 0009-241X
DOI	10.1039/b908664c
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Article ; Online: Rapid assembly of oligosaccharides: a highly convergent strategy for the assembly of a glycosylated amino acid derived from PSGL-1.

Vohra, Yusuf / Buskas, Therese / Boons, Geert-Jan

The Journal of organic chemistry

2009 Volume 74, Issue 16, Page(s) 6064–6071

Abstract: P-Selectin and P-selectin glycoprotein ligand 1 (PSGL-1) are vascular adhesion molecules that play an important role in the recruitment of leukocytes to inflamed tissue by establishing leukocyte-endothelial and leukocyte-platelet interaction. P-Selectin ... ...

Abstract	P-Selectin and P-selectin glycoprotein ligand 1 (PSGL-1) are vascular adhesion molecules that play an important role in the recruitment of leukocytes to inflamed tissue by establishing leukocyte-endothelial and leukocyte-platelet interaction. P-Selectin binds to the amino-terminus of PSGL-1 through recognition of a sialyl Lewis(x) (SLe(x)) moiety linked to a properly positioned core-2 O-glycan and three tyrosine sulfate residues. We have developed a highly convergent synthesis of the PSGL-1 oligosaccharide linked to threonine based on the use of trichoroacetimidate donors and thioglycosyl acceptors that give products that can immediately be employed in a subsequent glycosylation step without the need for protecting group manipulations. Furthermore, by employing one-pot multistep glycosylation sequences the number of purification steps could be minimized. The process of oligosaccharide assembly was further streamlined by combining protecting group manipulations and glycosylations as a one-pot multistep synthetic procedure. The resulting PSGL-1 oligosaccharide is properly protected for glycopeptide assembly. It is to be expected that the strategic principles employed for the synthesis of the target compound can be applied for the preparation of other complex oligosaccharides of biological and medical importance.
MeSH term(s)	Glycopeptides/chemistry ; Glycosylation ; Kinetics ; Membrane Glycoproteins/chemistry ; Oligosaccharides/chemical synthesis ; Oligosaccharides/chemistry ; Thioglycosides/chemistry ; Threonine/chemistry
Chemical Substances	Glycopeptides ; Membrane Glycoproteins ; Oligosaccharides ; P-selectin ligand protein ; Thioglycosides ; Threonine (2ZD004190S)
Language	English
Publishing date	2009-05-11
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/jo901135k
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Article: Glycopeptides as versatile tools for glycobiology

Buskas, Therese / Ingale, Sampat / Boons, Geert-Jan

Glycobiology. 2006 Aug., v. 16, no. 8

2006

Abstract: This review describes the recent advances in the field of glycopeptide and small glycoprotein synthesis. The strategies covered include chemical and chemoenzymatic synthesis, native chemical ligation (NCL), and expressed chemical ligation. The importance ...

Abstract	This review describes the recent advances in the field of glycopeptide and small glycoprotein synthesis. The strategies covered include chemical and chemoenzymatic synthesis, native chemical ligation (NCL), and expressed chemical ligation. The importance of glycopeptide synthesis is exemplified by giving the reader an overview of how versatile and important these well-defined glycopeptides are as tools in glycobiology.
Keywords	glycopeptides ; glycoproteins ; research ; synthesis
Language	English
Dates of publication	2006-08
Size	p. 113R-136R.
Publishing place	Oxford University Press
Document type	Article
ZDB-ID	1067689-2
ISSN	1460-2423 ; 0959-6658
ISSN (online)	1460-2423
ISSN	0959-6658
DOI	10.1093/glycob/cwj125
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Article: Glycopeptides as versatile tools for glycobiology.

Buskas, Therese / Ingale, Sampat / Boons, Geert-Jan

Glycobiology

2006 Volume 16, Issue 8, Page(s) 113R–136R

Abstract	This review describes the recent advances in the field of glycopeptide and small glycoprotein synthesis. The strategies covered include chemical and chemoenzymatic synthesis, native chemical ligation (NCL), and expressed chemical ligation. The importance of glycopeptide synthesis is exemplified by giving the reader an overview of how versatile and important these well-defined glycopeptides are as tools in glycobiology.
MeSH term(s)	Biology ; Glycopeptides/chemical synthesis ; Glycoproteins/chemical synthesis ; Models, Chemical ; Oligosaccharides/chemical synthesis
Chemical Substances	Glycopeptides ; Glycoproteins ; Oligosaccharides
Language	English
Publishing date	2006-08
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Review
ZDB-ID	1067689-2
ISSN	1460-2423 ; 0959-6658
ISSN (online)	1460-2423
ISSN	0959-6658
DOI	10.1093/glycob/cwj125
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Article: Synthesis of glyco(lipo)peptides by liposome-mediated native chemical ligation.

Ingale, Sampat / Buskas, Therese / Boons, Geert-Jan

Organic letters

2006 Volume 8, Issue 25, Page(s) 5785–5788

Abstract: Although native chemical ligation (NCL) is emerging as a powerful method for the assembly of (glyco)peptide building blocks, its applicability is reduced when peptide segments are poorly soluble in aqueous buffer. We have found that incorporating ... ...

Abstract	Although native chemical ligation (NCL) is emerging as a powerful method for the assembly of (glyco)peptide building blocks, its applicability is reduced when peptide segments are poorly soluble in aqueous buffer. We have found that incorporating reactants in liposomes allows NCL of lipophilic peptides and lipopeptides. Furthermore, the reaction rates of liposome-mediated NCL are higher than traditional reaction conditions resulting in improved yields. [reaction: see text]
MeSH term(s)	Amino Acid Sequence ; Buffers ; Cancer Vaccines/chemistry ; Epitopes ; Glycopeptides/chemical synthesis ; Glycopeptides/chemistry ; Indicators and Reagents ; Liposomes/chemistry ; Molecular Sequence Data ; Mucin-1/chemistry ; Solubility
Chemical Substances	Buffers ; Cancer Vaccines ; Epitopes ; Glycopeptides ; Indicators and Reagents ; Liposomes ; Mucin-1
Language	English
Publishing date	2006-12-07
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ISSN	1523-7060
ISSN	1523-7060
DOI	10.1021/ol062423x
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Article: Towards a fully synthetic carbohydrate-based anticancer vaccine: synthesis and immunological evaluation of a lipidated glycopeptide containing the tumor-associated tn antigen.

Buskas, Therese / Ingale, Sampat / Boons, Geert-Jan

Angewandte Chemie (International ed. in English)

2005 Volume 44, Issue 37, Page(s) 5985–5988

MeSH term(s)	Amino Acid Sequence ; Antigens, Tumor-Associated, Carbohydrate/immunology ; Cancer Vaccines/chemical synthesis ; Cancer Vaccines/chemistry ; Cancer Vaccines/immunology ; Carbohydrate Conformation ; Carbohydrates/chemical synthesis ; Carbohydrates/chemistry ; Carbohydrates/immunology ; Drug Evaluation, Preclinical ; Glycopeptides/chemistry ; Glycopeptides/immunology ; Lipids/chemistry ; Molecular Sequence Data
Chemical Substances	Antigens, Tumor-Associated, Carbohydrate ; Cancer Vaccines ; Carbohydrates ; Glycopeptides ; Lipids ; Tn antigen
Language	English
Publishing date	2005-09-19
Publishing country	Germany
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.200501818
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Article ; Online: Increasing the antigenicity of synthetic tumor-associated carbohydrate antigens by targeting Toll-like receptors.

Ingale, Sampat / Wolfert, Margreet A / Buskas, Therese / Boons, Geert-Jan

Chembiochem : a European journal of chemical biology

2009 Volume 10, Issue 3, Page(s) 455–463

Abstract: SYNTHETIC CANCER VACCINES: A number of fully synthetic vaccine candidates have been designed, chemically synthesized, and immunologically evaluated to establish a strategy to overcome the poor immunogenicity of tumor-associated carbohydrates and ... ...

Abstract	SYNTHETIC CANCER VACCINES: A number of fully synthetic vaccine candidates have been designed, chemically synthesized, and immunologically evaluated to establish a strategy to overcome the poor immunogenicity of tumor-associated carbohydrates and glycopeptides and to determine the importance of Toll-like receptor (TLR) engagement for antigenic responses against these compounds.Epithelial cancer cells often overexpress mucins that are aberrantly glycosylated. Although it has been realized that these compounds offer exciting opportunities for the development of immunotherapy for cancer, their use is hampered by the low antigenicity of classical immunogens composed of a glycopeptide derived from a mucin conjugated to a foreign carrier protein. We have designed, chemically synthesized, and immunologically evaluated a number of fully synthetic vaccine candidates to establish a strategy to overcome the poor immunogenicity of tumor-associated carbohydrates and glycopeptides. The compounds were also designed to allow study of the importance of Toll-like receptor (TLR) engagement for these antigenic responses in detail. We have found that covalent attachment of a TLR2 agonist, a promiscuous peptide T-helper epitope, and a tumor-associated glycopeptide gives a compound (1) that elicits in mice exceptionally high titers of IgG antibodies that recognize MCF7 cancer cells expressing the tumor-associated carbohydrate. Immunizations with glycolipopeptide 2, which contains lipidated amino acids instead of a TLR2 ligand, gave significantly lower titers of IgG antibodies; this demonstrates that TLR engagement is critical for optimum antigenic responses. Although mixtures of compound 2 with Pam(3)CysSK(4) (3) or monophosphoryl lipid A (4) elicited titers of IgG antibodies similar to those seen with 1, the resulting antisera had impaired ability to recognize cancer cells. It was also found that covalent linkage of the helper T-epitope to the B-epitope is essential, probably because internalization of the helper T-epitope by B-cells requires assistance of the B-epitope. The results presented here show that synthetic vaccine development is amenable to structure-activity relationship studies for successful optimization of carbohydrate-based cancer vaccines.
MeSH term(s)	Amino Acid Sequence ; Animals ; Antigens, Tumor-Associated, Carbohydrate/chemistry ; Antigens, Tumor-Associated, Carbohydrate/genetics ; Antigens, Tumor-Associated, Carbohydrate/immunology ; Cancer Vaccines/chemical synthesis ; Cancer Vaccines/immunology ; Cell Line ; Epitopes ; Female ; Humans ; Macrophages/cytology ; Macrophages/immunology ; Mice ; Mice, Inbred BALB C ; Molecular Sequence Data ; Molecular Structure ; Mucin-1/genetics ; Mucin-1/immunology ; Protein Engineering ; Recombinant Proteins/genetics ; Recombinant Proteins/immunology ; Toll-Like Receptors/genetics ; Toll-Like Receptors/immunology
Chemical Substances	Antigens, Tumor-Associated, Carbohydrate ; Cancer Vaccines ; Epitopes ; Mucin-1 ; Recombinant Proteins ; Toll-Like Receptors
Language	English
Publishing date	2009-01-14
Publishing country	Germany
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	2020469-3
ISSN	1439-7633 ; 1439-4227
ISSN (online)	1439-7633
ISSN	1439-4227
DOI	10.1002/cbic.200800596
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Article: Synthesis of a dimeric Lewis antigen and the evaluation of the epitope specificity of antibodies elicited in mice.

Buskas, Therese / Li, Yanhong / Boons, Geert-Jan

Chemistry (Weinheim an der Bergstrasse, Germany)

2005 Volume 11, Issue 18, Page(s) 5457–5467

Abstract: The Lewis(y)-Lewis(x) heptasaccharide, modified by an artificial aminopropyl spacer, was synthesized by an approach that employed two orthogonally protected lactosamine building blocks. A p-(benzoyl)-benzyl glycoside was used as a novel anomeric ... ...

Abstract	The Lewis(y)-Lewis(x) heptasaccharide, modified by an artificial aminopropyl spacer, was synthesized by an approach that employed two orthogonally protected lactosamine building blocks. A p-(benzoyl)-benzyl glycoside was used as a novel anomeric protecting group, which could be selectively removed at a late stage in the synthesis, thus offering the benefit of enhanced flexibility. The artificial aminopropyl moiety was modified by a thioacetyl group, which allowed an efficient conjugation to keyhole limpet hemocyanin (KLH) that had been activated with electrophilic 3-(bromoacetamido)-propionyl groups. Mice were immunized with the Le(y)Le(x)-BrAc-KLH antigen. Analysis of the sera by ELISA established that a strong helper T-cell immune response was raised against the Le(y)Le(x) saccharide. Further ELISA analysis showed that the titer for monomeric Le(y) tetrasaccharide was tenfold lower whereas recognition of the Le(x) trisaccharide was negligible.
MeSH term(s)	Animals ; Antibody Specificity ; Carbohydrate Sequence ; Carbohydrates/chemistry ; Dimerization ; Epitopes/chemistry ; Epitopes/immunology ; Female ; Lewis X Antigen/chemistry ; Lewis X Antigen/immunology ; Mice ; Mice, Inbred BALB C ; Molecular Sequence Data ; Nuclear Magnetic Resonance, Biomolecular ; Proteins/chemistry ; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Chemical Substances	Carbohydrates ; Epitopes ; Lewis X Antigen ; Proteins
Language	English
Publishing date	2005-09-05
Publishing country	Germany
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	1478547-x
ISSN	1521-3765 ; 0947-6539
ISSN (online)	1521-3765
ISSN	0947-6539
DOI	10.1002/chem.200500412
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