Organic and Biomolecular Chemistry p. 3347 - 3353 (2007)
Update date:2022-08-03
Topics:
Patrick, Michael J.
Ernst, Lauren A.
Waggoner, Alan S.
Thai, Dung
Tai, Dean
Salama, Guy
Long wavelength voltage-sensitive dyes (VSDs) called Pittsburgh (PGH) dyes were recently synthesized by coupling various heterocyclic groups to a styryl-thiophene intermediate forming extended, partially rigid chromophores. Unlike most styryl VSDs, dyes with a sulfonic acid anchor directly attached to the chromophore showed no solvatochromic absorption shifts. The limited water solubility of many long wavelength VSDs requires the use of surfactants to transport the dye through physiological saline solutions and effectively label biological membranes. Here, we tested the chemical substitution of the sulfonic acid moiety with polyethyleneglycol (PEG) chains, ranging from MW 750 to 5000, to overcome the poor solubility of VSDs while retaining their properties as VSDs. The chemical synthesis of PGH dyes and their PEG derivatives are described. The PEG derivatives were soluble in aqueous solutions (>1 mM) and still reported membrane potential changes. In frog and mouse hearts, the voltage sensitivity (ΔF/F per action potential) and spectral properties of PEG dyes were the same as the sulfonated analogues. Thus, the solubility of VSDs can be considerably improved with small polyethyleneglycol chains and can provide an effective approach to improve staining of excitable tissues and optical recordings of membrane potential. The Royal Society of Chemistry.
View MoreShanghai Sinofluoro Scientific Co., Ltd
Contact:+86-21-64279360
Address:Room 1006,Building 3,#58 East Xinjian Road, Shanghai ,201100,China,
JIANGXI AIFEIMU TECHNOLOGY CO.,LTD
Contact:+86-570-6040289
Address:FINECHEMICAL PARK,ZIBU TOWN,WANNIAN COUNTY,JIANGXI PROV.,CHINA,ZIP
Quzhou Aokai Chemical Co., Ltd.
Contact:86-570-3032832
Address:NO.16 , Laodong Road,Quzhou City, Zhejiang Province,China
Shijiazhuang Haotian Chemical Co., Ltd.
Contact:86-311-85044374
Address:293 Donggang Road
ZHIJIANG ZENVA SINO COMMERCE AND TRADE CO., LTD.
website:http://www.zenvasino.com
Contact:+86-138-72658998
Address:Shibeishan Road,Zhijiang, Hubei, China
Doi:10.1021/jo990242l
(1999)Doi:10.1002/anie.199706211
(1997)Doi:10.1039/a700702g
(1997)Doi:10.1039/a605827b
(1997)Doi:10.1039/c19670000922
(1967)Doi:10.1021/ja01618a080
(1955)