Hydrophilic and lipophilic rhodamines for labelling and imaging

US8580579B2 · kind B2 · utility

Assignee

• Max-Planck-Gesellschaft zur Föderung der Wissenschaften e.V. · US

Inventors

• Stefan W. Hell · Oebisfelde, DE
• Vladimir N. Belov · Oettingen, DE
• Kirill Kolmakov · Saint Petersburg, RU
• Volker Westphal · Hannover, DE
• Marcel Lauterbach · Oettingen, DE
• Stefan Jakobs · Oettingen, DE
• Christian Wurm · Oettingen, DE
• Christian Eggeling · Oettingen, DE
• Christian Ringemann · Oettingen, DE

Key dates

• Filing date: Apr 26, 2010
• Grant date: Nov 12, 2013
• Expiry date: Jul 2, 2030

Classification

• Technology area (CPC G): Physics
• CPC primary: G01N33/582
• WIPO field: Measurement
• WIPO sector: Instruments

Abstract

The invention relates to novel and improved photostable rhodamine dyes of the general structural formulae I or II and their uses as fluorescent markers, e.g. for immunostainings and spectroscopic and microscopic applications, in particular in conventional and stimulated emission depletion (STED) microscopy and fluorescence correlation spectroscopy. The partially deuterated analogues are useful as molecular mass distribution tags in mass spectroscopic applications, wherein R1=an unsubstituted or substituted alkyl group, including a cycloalkyl group, or heterocycloalkyl group; R2=H, an unsubstituted or substituted alkyl group, including a cycloalkyl group, or heterocycloalkyl group, or an unsubstituted or substituted aryl group or heteroaryl group, or any combination of such groups; X=CH2, C═O, C═NORa, C═NNRaNRb, CH(ORa), O, S, SO, SO2, or any other derivatives of these groups, with Ra and Rb independently being H or an organic residue, in particular an unsubstituted or substituted (cyclo)alkyl group or heterocycloalkyl group, an unsubstituted or substituted aryl group or heteroaryl group; Z=a negatively charged group with 1, 2, 3, 4 or 5 charges per anion.