The invention relates to novel fluorescent rhodamine dyes with enhanced cell permeability which are rhodamine 4′-isomers having the following general structural formula A: wherein Z is selected from O(alkyl), O(aryl), S(aryl), S(O)(alkyl), S(O) (aryl), S(O).sub.2(alkyl), S(O).sub.2(aryl), S(O).sub.2(—O-alkyl), S(O).sub.2(—O-aryl), S(O).sub.2NH(alkyl), S(O).sub.2NH(aryl), S(O).sub.2N(alkyl).sub.2, S(O).sub.2N(aryl).sub.2, S(O).sub.2N(alkyl)(aryl), C(O)O(alkyl), C(O)O(aryl), C(O)(alkyl), C(O)(aryl), P(O)OH(—NH-alkyl), P(O)OH(—O-alkyl), P(O)OH(—NH-aryl), P(O)OH(—O-aryl), P(O)(—O-alkyl).sub.2, P(O)(—NH-alkyl).sub.2, P(O)OH(—N(alkyl).sub.2), P(O)OH(—N(aryl).sub.2), P(O)(—N(aryl).sub.2).sub.2, P(O) (—N(alkyl).sub.2)(—N(alkyl).sub.2), P(O)(—O-aryl).sub.2, P(O)(—NH-aryl).sub.2, P(O)(—O-alkyl)(-O-aryl), P(O)(—NH-alkyl)(-O-aryl), P(O)(-O-alkyl)(-NH-aryl), P(O)(—NH-alkyl)(-NH-aryl), C(O)OH, C(O)NH(alkyl), C(O)NH(aryl), CON(alkyl).sub.2, CON(aryl).sub.2, in particular C(O)OH, C(O)NH(alkyl), C(O)NH(aryl), CON(alkyl).sub.2, CON(aryl).sub.2, C(O)O(alkyl) and C(O)O(aryl), or any group which is neither Cl, NH.sub.2 or NO.sub.2 and which induces a neighboring group effect via steric, ionic or bonding interactions with the adjacent carboxyl group resulting in a shift of the equilibrium between zwitterionic form and spirolactone form towards the spirolactone form. The invention further relates to 4′-isomer derivatives and probes comprising such 4′-isomers coupled to at least one reactive group or ligand which is capable to interact with or bind to other molecules, wherein said reactive group or ligand may be coupled to the rhodamine 4′-isomer fluorophore either directly or via a linker. Another aspect of the invention relates to the use of these compounds and conjugates as labels in microscopic, spectroscopic and other imaging techniques and/or as cell permeable substances penetrating through membranes of living and fixed cells in vivo or in vitro.

##STR00001##

The invention relates to novel fluorescent rhodamine dyes with enhanced cell permeability which are rhodamine 4′-isomers having the following general structural formula A: wherein Z is selected from O(alkyl), O(aryl), S(aryl), S(O)(alkyl), S(O) (aryl), S(O).sub.2(alkyl), S(O).sub.2(aryl), S(O).sub.2(—O-alkyl), S(O).sub.2(—O-aryl), S(O).sub.2NH(alkyl), S(O).sub.2NH(aryl), S(O).sub.2N(alkyl).sub.2, S(O).sub.2N(aryl).sub.2, S(O).sub.2N(alkyl)(aryl), C(O)O(alkyl), C(O)O(aryl), C(O)(alkyl), C(O)(aryl), P(O)OH(—NH-alkyl), P(O)OH(—O-alkyl), P(O)OH(—NH-aryl), P(O)OH(—O-aryl), P(O)(—O-alkyl).sub.2, P(O)(—NH-alkyl).sub.2, P(O)OH(—N(alkyl).sub.2), P(O)OH(—N(aryl).sub.2), P(O)(—N(aryl).sub.2).sub.2, P(O) (—N(alkyl).sub.2)(—N(alkyl).sub.2), P(O)(—O-aryl).sub.2, P(O)(—NH-aryl).sub.2, P(O)(—O-alkyl)(-O-aryl), P(O)(—NH-alkyl)(-O-aryl), P(O)(-O-alkyl)(-NH-aryl), P(O)(—NH-alkyl)(-NH-aryl), C(O)OH, C(O)NH(alkyl), C(O)NH(aryl), CON(alkyl).sub.2, CON(aryl).sub.2, in particular C(O)OH, C(O)NH(alkyl), C(O)NH(aryl), CON(alkyl).sub.2, CON(aryl).sub.2, C(O)O(alkyl) and C(O)O(aryl), or any group which is neither Cl, NH.sub.2 or NO.sub.2 and which induces a neighboring group effect via steric, ionic or bonding interactions with the adjacent carboxyl group resulting in a shift of the equilibrium between zwitterionic form and spirolactone form towards the spirolactone form. The invention further relates to 4′-isomer derivatives and probes comprising such 4′-isomers coupled to at least one reactive group or ligand which is capable to interact with or bind to other molecules, wherein said reactive group or ligand may be coupled to the rhodamine 4′-isomer fluorophore either directly or via a linker. Another aspect of the invention relates to the use of these compounds and conjugates as labels in microscopic, spectroscopic and other imaging techniques and/or as cell permeable substances penetrating through membranes of living and fixed cells in vivo or in vitro.

##STR00001##

The present invention relates generally to novel rhodamine dyes which upon conjugation with another molecule form single isomeric conjugation products. These novel rhodamine dyes contain only one single functional group on the rhodomine molecule for conjugation so that their conjugation products are single isomeric conjugation products.

The present invention relates generally to novel rhodamine dyes which upon conjugation with another molecule form single isomeric conjugation products. These novel rhodamine dyes contain only one single functional group on the rhodomine molecule for conjugation so that their conjugation products are single isomeric conjugation products.

The carborhodamine dyes disclosed herein are novel reagents suitable for automated incorporation of carborhodamine dyes into oligonucleotides that can be used in detection methods for nucleic acid targets. This disclosure provides an efficient and simple process for the preparation of carborhodamine compounds and introduces previously unknown reagents for the automated synthesis of oligonucleotide-carborhodamine conjugates.

The carborhodamine dyes disclosed herein are novel reagents suitable for automated incorporation of carborhodamine dyes into oligonucleotides that can be used in detection methods for nucleic acid targets. This disclosure provides an efficient and simple process for the preparation of carborhodamine compounds and introduces previously unknown reagents for the automated synthesis of oligonucleotide-carborhodamine conjugates.

Provided are a lithographic printing plate precursor comprising: an image-recording layer on a support, in which the image-recording layer includes a dye compound having a decomposable group that is decomposed by an acid, heat, or both and a structure in which decomposition of the decomposable group opens a ring or desorbs a leaving group and an electron-donating polymerization initiator, a method for producing a lithographic printing plate in which the lithographic printing plate precursor is used, and a color-developing composition including a dye compound having a decomposable group that is decomposed by an acid, heat, or both and a structure in which decomposition of the decomposable group opens a ring or desorbs a leaving group and an electron-donating polymerization initiator.

Disclosed herein are detectable moieties and detectable conjugates comprising one or more detectable moieties. In some embodiments, the disclosed detectable moieties have a narrow wavelength and are suitable for multiplexing. Also disclosed are methods of labeling one or more targets within a biological specimen using any of the detectable conjugates and/or detectable moieties described herein.

Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I):

##STR00001##

including stereoisomers, salts and tautomers thereof, wherein R.sup.1, R.sup.2, R.sup.3, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, M.sup.1, M.sup.2, A, q, w and n are as defined herein. Methods associated with preparation and use of such compounds are also provided.

Compounds useful as fluorescent or colored dyes are disclosed. The compounds have the following structure (I):

##STR00001##

including stereoisomers, salts and tautomers thereof, wherein R.sup.1, R.sup.2, R.sup.3, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, L.sup.6, M.sup.1, M.sup.2, A, q, w and n are as defined herein. Methods associated with preparation and use of such compounds are also provided.