Synthesis of dansyl labeled sphingosine kinase 1 inhibitor

Eun Young Park; Taeho Lee; Yoon Sin Oh; Joo Youn Lee; Jitendra Shrestha; Seung Woo Hong; Yun Ji Jin; Geun Hyung Jo; Sanghee Kim; Gil Tae Hwang; Dong Sul Han; Dong Jae Baek

doi:10.1016/j.chemphyslip.2018.07.005

Synthesis of dansyl labeled sphingosine kinase 1 inhibitor

Eun Young Park
, Taeho Lee
, Yoon Sin Oh
, Joo Youn Lee
, Jitendra Shrestha
, Seung Woo Hong
, Yun Ji Jin
, Geun Hyung Jo
, Sanghee Kim
, Gil Tae Hwang
, Dong Sul Han
, Dong Jae Baek

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

PF-543 is a non-sphingosine analogue with inhibitory effect against SK1, based on a Ki of 4.3 nM and 130-fold selectivity for SK1 over SK2. Since the development of PF-543, animal studies demonstrated its valuable role in multiple sclerosis, myocardial infarction, and colorectal cancer. We synthesized labeled PF-543 for biochemical studies involving SK1. Overall, the 8-step synthetic route used 3,5-dimethylphenol as the starting material. A docking study of SK1 and SK1 inhibitory activity confirmed the structural similarity between the synthetic dansyl-PF-543 and PF-543. We also provide fluorescence spectra of dansyl-PF-543.

Original language	English
Pages (from-to)	29-33
Number of pages	5
Journal	Chemistry and Physics of Lipids
Volume	215
DOIs	https://doi.org/10.1016/j.chemphyslip.2018.07.005
State	Published - Sep 2018

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Cancer
Dansyl
Inhibitor
Label
PF-543
Sphingosine kinase

Access to Document

10.1016/j.chemphyslip.2018.07.005

Cite this

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title = "Synthesis of dansyl labeled sphingosine kinase 1 inhibitor",

abstract = "PF-543 is a non-sphingosine analogue with inhibitory effect against SK1, based on a Ki of 4.3 nM and 130-fold selectivity for SK1 over SK2. Since the development of PF-543, animal studies demonstrated its valuable role in multiple sclerosis, myocardial infarction, and colorectal cancer. We synthesized labeled PF-543 for biochemical studies involving SK1. Overall, the 8-step synthetic route used 3,5-dimethylphenol as the starting material. A docking study of SK1 and SK1 inhibitory activity confirmed the structural similarity between the synthetic dansyl-PF-543 and PF-543. We also provide fluorescence spectra of dansyl-PF-543.",

keywords = "Cancer, Dansyl, Inhibitor, Label, PF-543, Sphingosine kinase",

author = "Park, \{Eun Young\} and Taeho Lee and Oh, \{Yoon Sin\} and Lee, \{Joo Youn\} and Jitendra Shrestha and Hong, \{Seung Woo\} and Jin, \{Yun Ji\} and Jo, \{Geun Hyung\} and Sanghee Kim and Hwang, \{Gil Tae\} and Han, \{Dong Sul\} and Baek, \{Dong Jae\}",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",

year = "2018",

month = sep,

doi = "10.1016/j.chemphyslip.2018.07.005",

language = "English",

volume = "215",

pages = "29--33",

journal = "Chemistry and Physics of Lipids",

issn = "0009-3084",

publisher = "Elsevier Ireland Ltd",

}

TY - JOUR

T1 - Synthesis of dansyl labeled sphingosine kinase 1 inhibitor

AU - Park, Eun Young

AU - Lee, Taeho

AU - Oh, Yoon Sin

AU - Lee, Joo Youn

AU - Shrestha, Jitendra

AU - Hong, Seung Woo

AU - Jin, Yun Ji

AU - Jo, Geun Hyung

AU - Kim, Sanghee

AU - Hwang, Gil Tae

AU - Han, Dong Sul

AU - Baek, Dong Jae

PY - 2018/9

Y1 - 2018/9

N2 - PF-543 is a non-sphingosine analogue with inhibitory effect against SK1, based on a Ki of 4.3 nM and 130-fold selectivity for SK1 over SK2. Since the development of PF-543, animal studies demonstrated its valuable role in multiple sclerosis, myocardial infarction, and colorectal cancer. We synthesized labeled PF-543 for biochemical studies involving SK1. Overall, the 8-step synthetic route used 3,5-dimethylphenol as the starting material. A docking study of SK1 and SK1 inhibitory activity confirmed the structural similarity between the synthetic dansyl-PF-543 and PF-543. We also provide fluorescence spectra of dansyl-PF-543.

AB - PF-543 is a non-sphingosine analogue with inhibitory effect against SK1, based on a Ki of 4.3 nM and 130-fold selectivity for SK1 over SK2. Since the development of PF-543, animal studies demonstrated its valuable role in multiple sclerosis, myocardial infarction, and colorectal cancer. We synthesized labeled PF-543 for biochemical studies involving SK1. Overall, the 8-step synthetic route used 3,5-dimethylphenol as the starting material. A docking study of SK1 and SK1 inhibitory activity confirmed the structural similarity between the synthetic dansyl-PF-543 and PF-543. We also provide fluorescence spectra of dansyl-PF-543.

KW - Cancer

KW - Dansyl

KW - Inhibitor

KW - Label

KW - PF-543

KW - Sphingosine kinase

UR - https://www.scopus.com/pages/publications/85050488396

U2 - 10.1016/j.chemphyslip.2018.07.005

DO - 10.1016/j.chemphyslip.2018.07.005

M3 - Article

C2 - 30044952

AN - SCOPUS:85050488396

SN - 0009-3084

VL - 215

SP - 29

EP - 33

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

ER -

Synthesis of dansyl labeled sphingosine kinase 1 inhibitor

Abstract

UN SDGs

Keywords

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