Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior

Jin Cui; Shigeru Matsuoka; Masanao Kinoshita; Nobuaki Matsumori; Fuminori Sato; Michio Murata; Jun Ando; Hiroyuki Yamakoshi; Kosuke Dodo; Mikiko Sodeoka

doi:10.1016/j.bmc.2015.05.014

Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior

Jin Cui, Shigeru Matsuoka, Masanao Kinoshita, Nobuaki Matsumori, Fuminori Sato, Michio Murata, Jun Ando, Hiroyuki Yamakoshi, Kosuke Dodo, Mikiko Sodeoka

Inorganic and Analytical Chemistry

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

18 Citations (Scopus)

Abstract

Abstract Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state ²H NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (L_o) domains in the raft-mimicking mixed bilayers.

Original language	English
Article number	12310
Pages (from-to)	2989-2994
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	23
Issue number	13
DOIs	https://doi.org/10.1016/j.bmc.2015.05.014
Publication status	Published - 2015

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2015.05.014

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@article{b8b6e1eb427d4d548a583c883a1b96c8,

title = "Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior",

abstract = "Abstract Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state 2H NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (Lo) domains in the raft-mimicking mixed bilayers.",

author = "Jin Cui and Shigeru Matsuoka and Masanao Kinoshita and Nobuaki Matsumori and Fuminori Sato and Michio Murata and Jun Ando and Hiroyuki Yamakoshi and Kosuke Dodo and Mikiko Sodeoka",

note = "Funding Information: We thank Mr. Tomokazu Yasuda for providing SM- d 2 , and Dr. Yuichi Umegawa for his kind support for 2 H NMR measurements. We also thank Dr. Sebastien Lethu for helpful discussions. This work was supported by Japanese Society of Technology (JST) ERATO , Lipid Active Structure Project, by AMED - CREST , Japan Agency for Medical Research and Development , and by Grant-In-Aids for Scientific Research (A) (No. 25242073 ) from MEXT, Japan . Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

doi = "10.1016/j.bmc.2015.05.014",

language = "English",

volume = "23",

pages = "2989--2994",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

number = "13",

}

TY - JOUR

T1 - Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior

AU - Cui, Jin

AU - Matsuoka, Shigeru

AU - Kinoshita, Masanao

AU - Matsumori, Nobuaki

AU - Sato, Fuminori

AU - Murata, Michio

AU - Ando, Jun

AU - Yamakoshi, Hiroyuki

AU - Dodo, Kosuke

AU - Sodeoka, Mikiko

N1 - Funding Information: We thank Mr. Tomokazu Yasuda for providing SM- d 2 , and Dr. Yuichi Umegawa for his kind support for 2 H NMR measurements. We also thank Dr. Sebastien Lethu for helpful discussions. This work was supported by Japanese Society of Technology (JST) ERATO , Lipid Active Structure Project, by AMED - CREST , Japan Agency for Medical Research and Development , and by Grant-In-Aids for Scientific Research (A) (No. 25242073 ) from MEXT, Japan . Publisher Copyright: © 2015 Elsevier Ltd.

PY - 2015

Y1 - 2015

N2 - Abstract Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state 2H NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (Lo) domains in the raft-mimicking mixed bilayers.

AB - Abstract Three Raman probes of sphingomyelin (SM) were synthesized and evaluated for their applicability to imaging experiments. One probe containing a hydroxymethyl-1,3-butadiyne moiety in the polar head group showed strong scattering. The solid-state 2H NMR spectra of this probe in oriented bilayer membrane revealed excellent compatibility with natural SM in phase behavior since the probe undergoes phase separation to form raft-like liquid ordered (Lo) domains in the raft-mimicking mixed bilayers.

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UR - http://www.scopus.com/inward/citedby.url?scp=84937409017&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2015.05.014

DO - 10.1016/j.bmc.2015.05.014

M3 - Article

C2 - 26026768

AN - SCOPUS:84937409017

SN - 0968-0896

VL - 23

SP - 2989

EP - 2994

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 13

M1 - 12310

ER -

Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior

Abstract

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