TY - JOUR
T1 - Efficient Strategy for the Preparation of Chemical Probes of Biologically Active Glycosides Using a Boron-Mediated Aglycon Delivery (BMAD) Method
AU - Kimura, Kosuke
AU - Yasunaga, Takeshi
AU - Makikawa, Takumi
AU - Takahashi, Daisuke
AU - Toshima, Kazunobu
N1 - Funding Information:
Materials for Biological Assay. The human colon cancer cell line, HCT116 (RCB2979), was provided by the RIKEN BRC through the National Bio-Resource Project of the MEXT, Japan. NeutrAvidin Agarose Resin was purchased from Thermo Scientific. 2D-Silver Stain Reagent II was purchased from COSMO BIO CO., LTD. Antibodies to Na+/K+/ATPase α1 (C464.6), α1 (F-2) or α3 (G-6) were purchased from Santa Cruz Biotechnology, Inc. An antibody to α-tubulin (10G10) was purchased from FUJIFILM Wako Pure Chemical Corporation. HRP-conjugated Affinipure Goat Anti-Mouse IgG (H + L) was purchased from Proreintech Group, Inc.
Funding Information:
This research was supported in part by JSPS KAKENHI Grant Number JP19H02724 in Scientific Research (B), JST CREST Grant Number JPMJCR20R3.
Publisher Copyright:
© 2022 The Chemical Society of Japan.
PY - 2022/7
Y1 - 2022/7
N2 - Development of an efficient method for the analysis and identification of the target proteins with which biologically active glycosides directly interact is highly desirable in many research fields. In this article, we report an efficient strategy for the preparation of chemical probes of biologically active glycosides using a reaction sequence of i) a boron-mediated aglycon delivery (BMAD) with an N3-functionalized 1,2-anhydroglu-cose donor, ii) deprotection, and iii) strain-promoted azidealkyne cycloaddition. Using the synthesized chemical probes, we successfully demonstrated that the target proteins of a cardiac glycoside, lanatoside C (1), can be visualized and identified in human colon cancer HCT116 cells.
AB - Development of an efficient method for the analysis and identification of the target proteins with which biologically active glycosides directly interact is highly desirable in many research fields. In this article, we report an efficient strategy for the preparation of chemical probes of biologically active glycosides using a reaction sequence of i) a boron-mediated aglycon delivery (BMAD) with an N3-functionalized 1,2-anhydroglu-cose donor, ii) deprotection, and iii) strain-promoted azidealkyne cycloaddition. Using the synthesized chemical probes, we successfully demonstrated that the target proteins of a cardiac glycoside, lanatoside C (1), can be visualized and identified in human colon cancer HCT116 cells.
KW - Boron-mediated aglycon delivery
KW - Chemical probes
KW - Late-stage glycosylation
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U2 - 10.1246/bcsj.20220076
DO - 10.1246/bcsj.20220076
M3 - Article
AN - SCOPUS:85136603048
SN - 0009-2673
VL - 95
SP - 1075
EP - 1082
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 7
ER -
