6′-Derivatised α-GalCer Analogues Capable of Inducing Strong CD1d-Mediated Th1-Biased NKT Cell Responses in Mice

Trappeniers, Matthias; Beneden, Katrien Van; Decruy, Tine; Hillaert, Ulrik; Linclau, Bruno; Elewaut, Dirk; Calenbergh, Serge Van

doi:10.1021/ja8064182

Cited by 66 publications

(59 citation statements)

References 28 publications

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“…[17,18] However, glycoside-modified a-GalCer analogues are scarce, consistent with the crucial interactions of galactose with CD1d and TCR proteins. These include modifications on the hydroxy groups, [19,20,21] replacement of the pyran oxygen by carbon, [22] or substitution of the anomeric oxygen by carbon (a-C-GalCer) [23] or sulfur (a-S-GalCer). [24,25] The iNKT cell stimulatory effects of these compounds are contrasting.…”

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confidence: 99%

“…[24,25] The iNKT cell stimulatory effects of these compounds are contrasting. Whereas a-S-GalCer is inactive, [25] the hydroxymethyl-modified analogues [20] and a-C-GalCer [26] are active in vivo. Interestingly, nonglycosidic a-GalCer analogues, bearing linear hydroxylated chains in place of galactose, [27] activate iNKT cells and induce a weaker but more sustained immune response than a-GalCer, [28] showing that the modulation of glycolipid activity after significant structural modifications of the galactose ring is feasible.…”

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confidence: 99%

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Aminocyclitol‐Substituted Phytoceramides and their Effects on iNKT Cell Stimulation

et al. 2009

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Aminocyclitol‐Substituted Phytoceramides and their Effects on iNKT Cell Stimulation

et al. 2009

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“…114) Calenbergh and co-workers developed 6 0 -amido and 6 0 -ureido analogs of 1 (41 and 42 respectively) in 2008. 115) They reported that these analogs showed a more pronounced Th1-bias in mice in vivo (i.p.). Among them, 6 0 -naphthylurea analog (NU--GalCer, 42) showed the most promising antitumor activity in mice in vivo.…”

Section: Modification Of the Sugar Part Of Krn7000mentioning

confidence: 99%

Structure-Activity Relationship Studies of Novel Glycosphingolipids That Stimulate Natural Killer T-Cells

Tashiro

2012

Bioscience, Biotechnology, and Biochemistry

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“…14 by modifi cation of the galactose 6-hydroxy group in 2008 (94). They expected that the aromatic ring of these analogues could interact by π-π stacking effect with the electron-rich indole ring of Trp153, which is placed nearby 6'-hydroxy group of 1 in human CD1d-1 complex (mouse CD1d: Gly155).…”

Section: E Modifi Cation Of the Sugar Part Of Krn7000mentioning

confidence: 99%

Fifteen Years since the Development of KRN7000 – Structure-Activity Relationship Studies on Novel Glycosphingolipids Which Stimulate Natural Killer T Cells

Tashiro¹,

Mori

2010

TIGG

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Invariant natural killer (NK) T cells bridge innate and acquired immunity and play an important role in both protective and regulatory responses. NKT cell responses are induced by recognition of a complex of glycolipid antigens with CD1d, an antigen presenting protein of the immune system, with its invariant T cell receptors. KRN7000, an α-galactosyl ceramide developed by KIRIN Brewery Co. in 1995, stimulates NKT cells strongly to induce the production of a large amount of cytokines, and is used as a standard reagent for a positive control of NKT cell studies. At the beginning, KRN7000 was developed as an anticancer drug candidate. However, it induces both helper T (Th)1-type cytokines, which induce immunostimulatory activity, and Th2-type ones, which induce immunosuppressive activities, in large quantities at the same time. Its therapeutical use, therefore, is limited. Fifteen years has passed since the discovery of KRN7000, and a number of analogues of KRN7000 have been developed worldwide to solve the above problem. Many researchers are also trying to understand how NKT cells recognize the structure of glycolipids and induce cytokines. In this minireview, we discuss the structure-activity relationship studies on novel glycolipids which stimulate NKT cells efficiently.

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6′-Derivatised α-GalCer Analogues Capable of Inducing Strong CD1d-Mediated Th1-Biased NKT Cell Responses in Mice

Cited by 66 publications

References 28 publications

Aminocyclitol‐Substituted Phytoceramides and their Effects on iNKT Cell Stimulation

Aminocyclitol‐Substituted Phytoceramides and their Effects on iNKT Cell Stimulation

Structure-Activity Relationship Studies of Novel Glycosphingolipids That Stimulate Natural Killer T-Cells

Fifteen Years since the Development of KRN7000 – Structure-Activity Relationship Studies on Novel Glycosphingolipids Which Stimulate Natural Killer T Cells

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