Novel Tn antigen-containing neoglycopeptides: Synthesis and evaluation as anti tumor vaccines

被引:58
作者
Cipolla, L [1 ]
Rescigno, M [1 ]
Leone, A [1 ]
Peri, F [1 ]
La Ferla, B [1 ]
Nicotra, F [1 ]
机构
[1] Univ Milan, Dept Biotechnol & Biosci, I-20126 Milan, Italy
关键词
D O I
10.1016/S0968-0896(01)00433-3
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The fully unprotected alpha-C-glycosyl analogue of N-acetylgalactosamine 9 was conjugated by a non-natural oxime bond to the segment peptides (328-340)OVA and (327-339)OVA, affording neoglycopeptides 1-2 and 3, having one or two sugar units, respectively. The three neoglycopeptides were tested in vitro in an antigen presentation assay as antitumor vaccines. Neoglycopeptides 1-3 could be presented to and recognized by the T cell receptor; neoglycopeptide 3, bearing two B-epitopes, was presented to the TCR with higher efficiency, compared to neoglycopeptide 2, having only one B-epitope. (C) 2002 Elsevier Science Ltd. All rights reserved.
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收藏
页码:1639 / 1646
页数:8
相关论文
共 95 条
[1]   IMMUNOGENICITY OF SYNTHETIC TF-KLH (KEYHOLE LIMPET HEMOCYANIN) AND STN-KLH CONJUGATES IN COLORECTAL-CARCINOMA PATIENTS [J].
ADLURI, S ;
HELLING, F ;
OGATA, S ;
ZHANG, SL ;
ITZKOWITZ, SH ;
LLOYD, KO ;
LIVINGSTON, PO .
CANCER IMMUNOLOGY IMMUNOTHERAPY, 1995, 41 (03) :185-192
[2]   Pursuit of optimal carbohydrate-based anticancer vaccines:: Preparation of a multiantigenic unimolecular glycopeptide containing the Tn, MBr1, and Lewisy antigens [J].
Allen, JR ;
Harris, CR ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :1890-1897
[3]  
Allen JR, 2000, CHEM-EUR J, V6, P1366, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1366::AID-CHEM1366>3.3.CO
[4]  
2-B
[5]  
Aller CT, 1996, AM J HEMATOL, V52, P29, DOI 10.1002/(SICI)1096-8652(199605)52:1<29::AID-AJH5>3.0.CO
[6]  
2-8
[7]  
Atherton E., 1989, SOLID PHASE PEPTIDE
[8]   Dendritic cells and the control of immunity [J].
Banchereau, J ;
Steinman, RM .
NATURE, 1998, 392 (6673) :245-252
[9]  
BAYS S, 1997, INT J PEPT PROT RES, V49, P620
[10]   Stereoselective synthesis of carbon-linked analogues of α- and β-galactoserine glycoconjugates using asymmetric enolate methodology [J].
Ben, RN ;
Orellana, A ;
Arya, P .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (14) :4817-4820