Rational design of a Tn antigen mimic

被引：21

作者：

Corzana, Francisco ^{[1
]}

Busto, Jesus H. ^{[1
]}

Marcelo, Filipa ^{[2
]}

Garcia de Luis, Marisa ^{[1
]}

Asensio, Juan L. ^{[3
]}

Martin-Santamaria, Sonsoles ^{[4
]}

Saenz, Yolanda

Torres, Carmen ^{[5
]}

Jimenez-Barbero, Jesus ^{[2
]}

Avenoza, Alberto ^{[1
]}

Peregrina, Jesus M. ^{[1
]}

机构：

[1] Univ La Rioja, Dept Quim, Ctr Invest Sintesis Quim, UA CSIC, Logrono 26006, Spain

[2] CSIC, Ctr Invest Biol, Madrid, Spain

[3] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

[4] Univ San Pablo CEU, Dept Quim, Fac Farm, Madrid, Spain

[5] Univ La Rioja, Area Microbiol Mol, Area Bioquim & Biol Mol, Ctr Invest Biomed La Rioja CIBIR, Logrono 26006, Spain

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 18期

关键词：

NONNATURAL AMINO-ACIDS; SYNTHETIC VACCINES; MUC1; GLYCOPEPTIDES; IMMUNOREACTIVE T; NMR-SPECTROSCOPY; BINDING; LECTIN; CARBOHYDRATE; PROTEIN; EPITOPE;

D O I：

10.1039/c1cc10192g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel Tn antigen mimic, in which the natural underlying amino acid has been replaced by the non-natural a-methylserine analogue, is reported. This derivative exhibits a similar affinity for a natural lectin as for the natural Tn and retains the bioactive conformation observed in the Tn-containing glycopeptides with anti-MUC1 antibodies.

引用

页码：5319 / 5321

页数：3

共 45 条

[1] Synthesis of a new conformationally constrained glycoamino acid building block [J].

Avenoza, A ;

Peregrina, JM ;

San Martín, E .

TETRAHEDRON LETTERS, 2003, 44 (34) :6413-6416

[2] Theoretical evidence for pyramidalized bicyclic serine enolates in highly diastereoselective alkylations [J].

Aydillo, Carlos ;

Jimenez-Oses, Gonzalo ;

Busto, Jesus H. ;

Peregrina, Jesus M. ;

Zurbano, Maria M. ;

Avenoza, Alberto .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (17) :4840-4848

[3] Synthesis and immunostimulating activity of a thioglycolipopeptide glycomimetic as a potential anticancer vaccine derived from Tn antigen [J].

Bousquet, E ;

Spadaro, A ;

Pappalardo, MS ;

Bernardini, R ;

Romeo, R ;

Panza, L ;

Ronsisvalle, G .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 2000, 19 (4-5) :527-541

[4] Antibody recognition of a unique tumor-specific glycopeptide antigen [J].

Brooks, Cory L. ;

Schietinger, Andrea ;

Borisova, Svetlana N. ;

Kufer, Peter ;

Okon, Mark ;

Hirama, Tomoko ;

MacKenzie, C. Roger ;

Wang, Lai-Xi ;

Schreiber, Hans ;

Evans, Stephen V. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (22) :10056-10061

[5]

BURCHELL J, 1987, CANCER RES, V47, P5476

[6] Immunotherapy for cancer: synthetic carbohydrate-based vaccines [J].

Buskas, Therese ;

Thompson, Pamela ;

Boons, Geert-Jan .

CHEMICAL COMMUNICATIONS, 2009, (36) :5335-5349

[7] Mucins and mucin binding proteins in colorectal cancer [J].

Byrd, JC ;

Bresalier, RS .

CANCER AND METASTASIS REVIEWS, 2004, 23 (1-2) :77-99

[8] Novel Tn antigen-containing neoglycopeptides: Synthesis and evaluation as anti tumor vaccines [J].

Cipolla, L ;

Rescigno, M ;

Leone, A ;

Peri, F ;

La Ferla, B ;

Nicotra, F .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (05) :1639-1646

[9] Dynamics and Hydration Properties of Small Antifreeze-Like Glycopeptides Containing Non-Natural Amino Acids [J].

Corzana, Francisco ;

Busto, Jesus H. ;

Garcia de Luis, Marisa ;

Fernandez-Tejada, Alberto ;

Rodriguez, Fernando ;

Jimenez-Barbero, Jesus ;

Avenoza, Alberto ;

Peregrina, Jestis M. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (18) :3525-3532

[10] MULTIVALENT LECTIN-CARBOHYDRATE INTERACTIONS: ENERGETICS AND MECHANISMS OF BINDING [J].

Dam, Tarun K. ;

Brewer, C. Fred .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 63, 2010, 63 :139-164

← 1 2 3 4 5 →