title: Novel Raman-tagged sphingomyelin that closely mimics original raft-forming behavior.
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 (2)H 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.
authors.affiliation: Department of Chemistry, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan; JST, ERATO, Lipid Active Structure Project, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan; Project Research Centre for Fundamental Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
authors.forename: Jin
authors.initials: J
authors.lastname: Cui
authors.affiliation: Department of Chemistry, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan; JST, ERATO, Lipid Active Structure Project, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan; Project Research Centre for Fundamental Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
authors.forename: Shigeru
authors.initials: S
authors.lastname: Matsuoka
authors.affiliation: Department of Chemistry, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan; JST, ERATO, Lipid Active Structure Project, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan; Project Research Centre for Fundamental Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
authors.forename: Masanao
authors.initials: M
authors.lastname: Kinoshita
authors.affiliation: Department of Chemistry, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Matsumori
authors.affiliation: JST, ERATO, Lipid Active Structure Project, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan; Project Research Centre for Fundamental Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
authors.forename: Fuminori
authors.initials: F
authors.lastname: Sato
authors.affiliation: Department of Chemistry, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan; JST, ERATO, Lipid Active Structure Project, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan; Project Research Centre for Fundamental Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan. Electronic address: murata@chem.sci.osaka-u.ac.jp.
authors.forename: Michio
authors.initials: M
authors.lastname: Murata
authors.affiliation: JST, ERATO, Sodeoka Live Cell Chemistry Project, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; AMED-CREST, AMED 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; Department of Applied Physics, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
authors.forename: Jun
authors.initials: J
authors.lastname: Ando
authors.affiliation: JST, ERATO, Sodeoka Live Cell Chemistry Project, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Yamakoshi
authors.affiliation: JST, ERATO, Sodeoka Live Cell Chemistry Project, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; AMED-CREST, AMED 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors.forename: Kosuke
authors.initials: K
authors.lastname: Dodo
authors.affiliation: JST, ERATO, Sodeoka Live Cell Chemistry Project, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; AMED-CREST, AMED 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors.forename: Mikiko
authors.initials: M
authors.lastname: Sodeoka
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000818:Animals; D002417:Cattle; D008051:Lipid Bilayers / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D021962:Membrane Microdomains / Q000737:chemistry; D018716:Molecular Mimicry; D015335:Molecular Probes / Q000737:chemistry*; D044367:Phase Transition; D010713:Phosphatidylcholines / Q000737:chemistry*; D013109:Sphingomyelins / Q000737:chemistry*
chemical_list: D000480:Alkynes; D008051:Lipid Bilayers; D015335:Molecular Probes; D010713:Phosphatidylcholines; D013109:Sphingomyelins; C017251:1,2-oleoylphosphatidylcholine
keywords: Lipid rafts; Phase distribution; Raman imaging; Solid-state (2)H NMR; Sphingomyelin