Photo effect on the CD1d-binding ability of azobenzene-attached analogues of α-GalCer.
Azobenzene
CD1d
Galactosylceramide
Photo-immunoregulation
iNKT
Journal
Bioorganic & medicinal chemistry letters
ISSN: 1464-3405
Titre abrégé: Bioorg Med Chem Lett
Pays: England
ID NLM: 9107377
Informations de publication
Date de publication:
01 03 2020
01 03 2020
Historique:
received:
20
11
2019
revised:
28
12
2019
accepted:
04
01
2020
pubmed:
27
1
2020
medline:
22
4
2021
entrez:
27
1
2020
Statut:
ppublish
Résumé
α-Galactosylceramide (α-GalCer) is recognized by the CD1d proteins on antigen-presenting cells at the ceramide moiety and the galactose moiety is presented to iNKT cells, which stimulates the immune responses. However, the immune suppression by repeated injections of α-GalCer has discouraged its development as an anti-cancer agent. To overcome the shortcoming by spatiotemporal restriction of its exposure, we synthesized the photochromic azobenzene-incorporated analogues and tested the photo-immunoregulation effect in its binding to CD1d. FACS analyses indicated that some of these analogues enhanced the affinity to CD1d on photo-irradiation by about 20%. A docking simulation suggests that the photochromic molecule should be bulkier for a clearer discrimination between on and off states.
Identifiants
pubmed: 31982233
pii: S0960-894X(20)30013-5
doi: 10.1016/j.bmcl.2020.126960
pii:
doi:
Substances chimiques
Antigens, CD1d
0
Azo Compounds
0
CD1D protein, human
0
Galactosylceramides
0
alpha-galactosylceramide
0
azobenzene
F0U1H6UG5C
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
126960Informations de copyright
Copyright © 2020 Elsevier Ltd. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.