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

Keywords

Cancer
Dansyl
Inhibitor
Label
PF-543
Sphingosine kinase

UN SDGs

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

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10.1016/j.chemphyslip.2018.07.005

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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",

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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 - http://www.scopus.com/inward/record.url?scp=85050488396&partnerID=8YFLogxK

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

Keywords

UN SDGs

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