Rational Design and Evaluation of a Branched‐Chain‐Containing Glycolipid Antigen That Binds to CD1d

Baek, Dong Jae; Lee, Yoon Sook; Lim, Chaemin; Lee, Doohyun; Lee, Tae‐Ho; Lee, Jae-Young; Lee, Kyoo‐A; Cho, Won‐Jea; Kang, Chang–Yuil; Kim, Sanghee

doi:10.1002/asia.201000120

Cited by 17 publications

(12 citation statements)

References 33 publications

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“…In 2010, Kim and coworkers [85] reported that their analog of 2 with a diheptylamino group at the end of the C 8 acyl chain (KBC-007, 22 in Fig. 23) induced enhanced but biased IL-4 production in mice in vitro.…”

Section: Modification Of the Acyl Chain: Kbc-007mentioning

confidence: 98%

Glycosphingolipid Ligands for Invariant Natural Killer T cells as Immunostimulants

Tashiro

Mori

2014

Studies in Natural Products Chemistry

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Section: Modification Of the Acyl Chain: Kbc-007mentioning

confidence: 98%

Glycosphingolipid Ligands for Invariant Natural Killer T cells as Immunostimulants

Tashiro

Mori

2014

Studies in Natural Products Chemistry

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“…The modification of the ceramide fragment of the glycolipid is broadly accepted as a sensitive 22 factor in terms of TH1/TH2 polarity. Derivatives in which the initial linear C26 acyl chain was replaced by unsaturated fatty acids, [91,92] branched [93] or amide containing [94] chain have been investigated and were suspected to use non-professional APC pathways to explain their TH2 polarisation tendency. [95] Conversely, heterocyclic substitutions of shortened N-acyl 26 chain derivatives mostly promote TH1 orientation by installing adequate - stacking in the CD1d pocket [96,97] as suggested by aromatic-ended alkyl chains.…”

Section: Fig 1 Structure Of α-Galactosylceramide Analoguesmentioning

confidence: 99%

3,4-Dideoxy-3,3,4,4-tetrafluoro- and 4-OH epimeric 3-deoxy-3,3-difluoro-α-GalCer analogues: Synthesis and biological evaluation on human iNKT cells stimulation

Golten

Patinec

Akoumany

et al. 2019

European Journal of Medicinal Chemistry

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HAL is a multidisciplinary open access archive for the deposit and dissemination of scientific research documents, whether they are published or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L'archive ouverte pluridisciplinaire HAL, est destinée au dépôt et à la diffusion de documents scientifiques de niveau recherche, publiés ou non, émanant des établissements d'enseignement et de recherche français ou étrangers, des laboratoires publics ou privés.

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“…Recently, Kim and his co-workers found that the analogue of 1 with a di(n-heptyl)amino group at the end of the acyl chain (9, Fig. 5) induced enhanced and biased IL-4 production in mice in vitro (55). According to the docking model of CD1d-9, two branched alkyl chains of the amino group of 9 effectively filled the donuts-type A' pocket.…”

Section: D-1 Modification Of the Two Lipid Alkyl Chains 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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Rational Design and Evaluation of a Branched‐Chain‐Containing Glycolipid Antigen That Binds to CD1d

Cited by 17 publications

References 33 publications

Glycosphingolipid Ligands for Invariant Natural Killer T cells as Immunostimulants

Glycosphingolipid Ligands for Invariant Natural Killer T cells as Immunostimulants

3,4-Dideoxy-3,3,4,4-tetrafluoro- and 4-OH epimeric 3-deoxy-3,3-difluoro-α-GalCer analogues: Synthesis and biological evaluation on human iNKT cells stimulation

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

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