Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)

Masao Shiozaki, Takuya Tashiro, Hiroyuki Koshino, Ryusuke Nakagawa, Sayo Inoue, Tomokuni Shigeura, Hiroshi Watarai, Masaru Taniguchi, Kenji Mori

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

These three ester analogues showed activity for IFNγ, and IL-4 production of iNKT cells. α-Galactosylceramide (αGalCer, KRN7000) has been identified as a modulator of immunological processes through its capacity to bind iNKT cells mediated by CD1d molecules. Some analogues in while the amide group in αGalCer is replaced with ester or ether groups were synthesized from d-arabinitol or l-ribose to evaluate their ability to activate iNKT cells. Ester analogues 30a, 31a, and 61 showed activity for IFNγ and IL-4 production of iNKT cells, while ether (31b) and 4-methoxy ester (76) analogues of α-galactosylceramide were not active for iNKT cells.

Original languageEnglish
Pages (from-to)1663-1684
Number of pages22
JournalCarbohydrate Research
Volume345
Issue number12
DOIs
Publication statusPublished - 2010 Aug 16
Externally publishedYes

Fingerprint

Galactosylceramides
Natural Killer T-Cells
Bioactivity
Ether
Esters
Interleukin-4
CD1d Antigen
Ribose
Amides
Modulators
KRN 7000

Keywords

  • Ester analogues of α-galactosylceramide
  • Glycolipid
  • Glycosylation
  • iNKT cells
  • KRN7000

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

Cite this

Shiozaki, M., Tashiro, T., Koshino, H., Nakagawa, R., Inoue, S., Shigeura, T., ... Mori, K. (2010). Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000). Carbohydrate Research, 345(12), 1663-1684. https://doi.org/10.1016/j.carres.2010.05.003

Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000). / Shiozaki, Masao; Tashiro, Takuya; Koshino, Hiroyuki; Nakagawa, Ryusuke; Inoue, Sayo; Shigeura, Tomokuni; Watarai, Hiroshi; Taniguchi, Masaru; Mori, Kenji.

In: Carbohydrate Research, Vol. 345, No. 12, 16.08.2010, p. 1663-1684.

Research output: Contribution to journalArticle

Shiozaki, M, Tashiro, T, Koshino, H, Nakagawa, R, Inoue, S, Shigeura, T, Watarai, H, Taniguchi, M & Mori, K 2010, 'Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)', Carbohydrate Research, vol. 345, no. 12, pp. 1663-1684. https://doi.org/10.1016/j.carres.2010.05.003
Shiozaki M, Tashiro T, Koshino H, Nakagawa R, Inoue S, Shigeura T et al. Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000). Carbohydrate Research. 2010 Aug 16;345(12):1663-1684. https://doi.org/10.1016/j.carres.2010.05.003
Shiozaki, Masao ; Tashiro, Takuya ; Koshino, Hiroyuki ; Nakagawa, Ryusuke ; Inoue, Sayo ; Shigeura, Tomokuni ; Watarai, Hiroshi ; Taniguchi, Masaru ; Mori, Kenji. / Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000). In: Carbohydrate Research. 2010 ; Vol. 345, No. 12. pp. 1663-1684.
@article{a79912705659493181283e569994c1ec,
title = "Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)",
abstract = "These three ester analogues showed activity for IFNγ, and IL-4 production of iNKT cells. α-Galactosylceramide (αGalCer, KRN7000) has been identified as a modulator of immunological processes through its capacity to bind iNKT cells mediated by CD1d molecules. Some analogues in while the amide group in αGalCer is replaced with ester or ether groups were synthesized from d-arabinitol or l-ribose to evaluate their ability to activate iNKT cells. Ester analogues 30a, 31a, and 61 showed activity for IFNγ and IL-4 production of iNKT cells, while ether (31b) and 4-methoxy ester (76) analogues of α-galactosylceramide were not active for iNKT cells.",
keywords = "Ester analogues of α-galactosylceramide, Glycolipid, Glycosylation, iNKT cells, KRN7000",
author = "Masao Shiozaki and Takuya Tashiro and Hiroyuki Koshino and Ryusuke Nakagawa and Sayo Inoue and Tomokuni Shigeura and Hiroshi Watarai and Masaru Taniguchi and Kenji Mori",
year = "2010",
month = "8",
day = "16",
doi = "10.1016/j.carres.2010.05.003",
language = "English",
volume = "345",
pages = "1663--1684",
journal = "Carbohydrate Research",
issn = "0008-6215",
publisher = "Elsevier BV",
number = "12",

}

TY - JOUR

T1 - Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)

AU - Shiozaki, Masao

AU - Tashiro, Takuya

AU - Koshino, Hiroyuki

AU - Nakagawa, Ryusuke

AU - Inoue, Sayo

AU - Shigeura, Tomokuni

AU - Watarai, Hiroshi

AU - Taniguchi, Masaru

AU - Mori, Kenji

PY - 2010/8/16

Y1 - 2010/8/16

N2 - These three ester analogues showed activity for IFNγ, and IL-4 production of iNKT cells. α-Galactosylceramide (αGalCer, KRN7000) has been identified as a modulator of immunological processes through its capacity to bind iNKT cells mediated by CD1d molecules. Some analogues in while the amide group in αGalCer is replaced with ester or ether groups were synthesized from d-arabinitol or l-ribose to evaluate their ability to activate iNKT cells. Ester analogues 30a, 31a, and 61 showed activity for IFNγ and IL-4 production of iNKT cells, while ether (31b) and 4-methoxy ester (76) analogues of α-galactosylceramide were not active for iNKT cells.

AB - These three ester analogues showed activity for IFNγ, and IL-4 production of iNKT cells. α-Galactosylceramide (αGalCer, KRN7000) has been identified as a modulator of immunological processes through its capacity to bind iNKT cells mediated by CD1d molecules. Some analogues in while the amide group in αGalCer is replaced with ester or ether groups were synthesized from d-arabinitol or l-ribose to evaluate their ability to activate iNKT cells. Ester analogues 30a, 31a, and 61 showed activity for IFNγ and IL-4 production of iNKT cells, while ether (31b) and 4-methoxy ester (76) analogues of α-galactosylceramide were not active for iNKT cells.

KW - Ester analogues of α-galactosylceramide

KW - Glycolipid

KW - Glycosylation

KW - iNKT cells

KW - KRN7000

UR - http://www.scopus.com/inward/record.url?scp=77955653859&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77955653859&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2010.05.003

DO - 10.1016/j.carres.2010.05.003

M3 - Article

C2 - 20591421

AN - SCOPUS:77955653859

VL - 345

SP - 1663

EP - 1684

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 12

ER -