Synthesis and evaluation of human T cell stimulating activity of an α-sulfatide analogue

Laura Franchini; Pamela Matto; Fiamma Ronchetti; Luigi Panza; Lucia Barbieri; Valeria Costantino; Alfonso Mangoni; Marco Cavallari; Lucia Mori; Gennaro De Libero

doi:10.1016/j.bmc.2007.05.044

Synthesis and evaluation of human T cell stimulating activity of an α-sulfatide analogue

Laura Franchini
, Pamela Matto
, Fiamma Ronchetti
, Luigi Panza
, Lucia Barbieri
, Valeria Costantino
, Alfonso Mangoni
, Marco Cavallari
, Lucia Mori
, Gennaro De Libero

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

Abstract

A concise synthesis of α-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the α-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated β-GalCer (sulfatide) and α-GalCer, which activate specific T cells. α-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than α-GalCer, while it was not recognized by CD1a-restricted sulfatide-specific T cells.

Original language	English
Pages (from-to)	5529-5536
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	15
Issue number	16
DOIs	https://doi.org/10.1016/j.bmc.2007.05.044
Publication status	Published - 15 Aug 2007

Keywords

Galactosylceramides
Glycosylation
Immunostimulation
NKT cell activation

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10.1016/j.bmc.2007.05.044

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@article{32bb4dbc420d4de9864b55118a8b1c1d,

title = "Synthesis and evaluation of human T cell stimulating activity of an α-sulfatide analogue",

abstract = "A concise synthesis of α-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the α-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated β-GalCer (sulfatide) and α-GalCer, which activate specific T cells. α-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than α-GalCer, while it was not recognized by CD1a-restricted sulfatide-specific T cells.",

keywords = "Galactosylceramides, Glycosylation, Immunostimulation, NKT cell activation",

author = "Laura Franchini and Pamela Matto and Fiamma Ronchetti and Luigi Panza and Lucia Barbieri and Valeria Costantino and Alfonso Mangoni and Marco Cavallari and Lucia Mori and \{De Libero\}, Gennaro",

note = "Funding Information: This work was supported by MIUR-Italy, COFIN 2004: “Structure and synthesis of glycolipids” (to F.R. and A.M.), the Swiss National Foundation Grant 3100A0-109918 (to G.D.L.), the MOLSTROKE project, Contract No. LSH-CT-2004-005206, funded under the EU FP6-2003 LIFESCIHEALTH programme (to G.D.L.), and the Swiss Society of Multiple Sclerosis, the University of Piemonte Orientale and IRCAD-Novara (to L.P.).",

year = "2007",

month = aug,

day = "15",

doi = "10.1016/j.bmc.2007.05.044",

language = "English",

volume = "15",

pages = "5529--5536",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd.",

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T1 - Synthesis and evaluation of human T cell stimulating activity of an α-sulfatide analogue

AU - Franchini, Laura

AU - Matto, Pamela

AU - Ronchetti, Fiamma

AU - Panza, Luigi

AU - Barbieri, Lucia

AU - Costantino, Valeria

AU - Mangoni, Alfonso

AU - Cavallari, Marco

AU - Mori, Lucia

AU - De Libero, Gennaro

N1 - Funding Information: This work was supported by MIUR-Italy, COFIN 2004: “Structure and synthesis of glycolipids” (to F.R. and A.M.), the Swiss National Foundation Grant 3100A0-109918 (to G.D.L.), the MOLSTROKE project, Contract No. LSH-CT-2004-005206, funded under the EU FP6-2003 LIFESCIHEALTH programme (to G.D.L.), and the Swiss Society of Multiple Sclerosis, the University of Piemonte Orientale and IRCAD-Novara (to L.P.).

PY - 2007/8/15

Y1 - 2007/8/15

N2 - A concise synthesis of α-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the α-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated β-GalCer (sulfatide) and α-GalCer, which activate specific T cells. α-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than α-GalCer, while it was not recognized by CD1a-restricted sulfatide-specific T cells.

AB - A concise synthesis of α-sulfatide 1, an analogue of natural glycolipid antigens with potential anti-tumor activity, was performed. Two different approaches to the α-glycosidic bond were explored, resulting in a high yield and excellent stereoselectivity. Compound 1 combines the structural features of sulfated β-GalCer (sulfatide) and α-GalCer, which activate specific T cells. α-Sulfatide 1 was stimulatory for CD1d-restricted semi-invariant Natural Killer T (iNKT) cell clones, although less potent than α-GalCer, while it was not recognized by CD1a-restricted sulfatide-specific T cells.

KW - Galactosylceramides

KW - Glycosylation

KW - Immunostimulation

KW - NKT cell activation

UR - https://www.scopus.com/pages/publications/34250903586

U2 - 10.1016/j.bmc.2007.05.044

DO - 10.1016/j.bmc.2007.05.044

M3 - Article

SN - 0968-0896

VL - 15

SP - 5529

EP - 5536

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 16

ER -

Synthesis and evaluation of human T cell stimulating activity of an α-sulfatide analogue

Abstract

Keywords

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