US 2023/0147145 A1Published application

Novel tunable photoactivatable silicon rhodamine fluorophores

AssigneeSpirochrome AG

InventorsKai JOHNSSON, Luc REYMOND, Michelle FREI, Stefan PITSCH

Life of this patent

Estimating the term…

Abstract

The invention relates to a compound characterized by general formula (100), wherein R1 and R6 are H or F, R2, R3, R4 and R5 can be any substituent, R7, R8, RN1, RN2, RN3 and RN4 are a hydrocarbon moiety, one of R9 and R10 is hydrogen and the other one is hydrogen or a saturated carbon atom connected to any substituent, and its use in staining and live cell fluorescence imaging.

Claims12

Dependent claims

A compound characterized by general formula (100):

wherein
R1 and R6 are independently selected from hydrogen and fluorine, particularly R1 and R6 are hydrogen;
R2, R3, R4 and R5 independently of each other is selected from H, halogen, SO3H, CO2H, NO2, CO2R, SO2R (with R being selected from C1 to C4 unsubstituted alkyl) and an unsubstituted or substituted (particularly unsubstituted or halogen-, amino-, hydroxyl-, SO3H- and/or carboxyl substituted) moiety selected from C1-C20 alkyl, C3-C8 cycloalkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C7-C20 alkylaryl, phenyl and 5- or 6-membered ring heteroaryl, or a combination thereof;
R7 and R8 are independently selected from:
unsubstituted and substituted C1-C12 alkyl, C3-C8 cycloalkyl, C2-C12 alkylene, C2-C12 alkylyne and C7-C12 alkylaryl;
unsubstituted or substituted 5- or 6-ring aryl, particularly phenyl, particularly wherein R7 is selected from H and a substituted or unsubstituted alkyl, alkenyl, alkenyl, alkylary or aryl having x carbon atoms and R8 is selected from H and a substituted or unsubstituted alkyl, alkenyl, alkenyl, alkylary or aryl having y carbon atoms and the sum of x and y is between 0 and 12, more particularly between 0 and 10, even more particularly between 0 and 8, even more particularly between 0 and 6;
RN1, RN2, RN3 and RN4 are:
independently selected from H, unsubstituted and substituted C1-C8 alkyl, C3-C8 cycloalkyl, C1-C4 acyl, and C7-C12 alkylaryl, and unsubstituted phenyl or phenyl substituted by COOH—, COOR, CONR2, unsubstituted alkyl, halogen, O-alkyl, and/or NO2;
or
RN1 together with RN2, and/or RN3 together with RN4 are a C3, C4, C6 unsubstituted or substituted alkyl forming a 3-7 sized ring structure;
or
RN1 and/or RN3 are independently selected from H and unsubstituted and substituted C1-C8 alkyl, C3-C8 cycloalkyl, and C7-C12 alkylaryl, and RN2 together with R2 or R3, and/or RN4 together with R4 or R5, is an unsubstituted or substituted C2, C3 or C4 alkyl, or an unsubstituted or substituted C2, C3 or C4 N-, O-, S-, or Se-alkyl;
one of R9 and R19 is hydrogen and the other one is hydrogen or a saturated carbon atom connected to a moiety selected from H, halogen, SO3H, CO2H, NO2, CO2R, SO2R (with R being selected from C1 to C4 unsubstituted alkyl) and an unsubstituted or substituted (particularly unsubstituted or halogen-, amino-, hydroxyl-, SO3H— and/or carboxyl substituted) moiety selected from C1-C20 alkyl, C3-C8 cycloalkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C7-C20 alkylaryl, phenyl and 5- or 6-membered ring heteroaryl, or a combination thereof
and wherein optionally the compound is covalently linked to a binding moiety M via any of the substituents.

11 more elements

A compound selected from:

a. 4-(3,7-Bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)butanoic acid (2a);
b. 4-(3,7-Bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)-3-methylbutanoic acid (3a);
c. N3,N3,N7,N7,5,5-Hexamethyl-10-propylidene-5,10-dihydrodibenzo[b,e]siline-3,7-diamine (4a);
d. N3,N3,N7,N7,5,5-Hexamethyl-10-methylene-5,10-dihydrodibenzo[b,e]siline-3,7-diamine (5a);
e. 3-(3,7-Bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)propanoic acid (22);
f. 4-(3,7-Bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)-2,2-dimethylbutanoic acid (28);
g. 4-(3,7-Bis(dimethylamino)-5,5-diisopropyldibenzo[b,e]silin-10(5H)-ylidene)butanoic acid (6a);
h. 4-(3,7-Bis(dimethylamino)-2,8-difluoro-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)butanoic acid (36)
i. 3-(3,7-Di(azetidin-1-yI)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)propanoic acid (42);
j. 4-(3,7-Bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)-N-(2-(2-((6-chlorohexyl)oxy)ethoxy)ethyl)butanamide (44);
k. 2,5-Dioxopyrrolidin-1-yl-4-(3,7-bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)butanoate (45);
l. N-(4-(((2-Amino-9H-purin-6-yl)oxy)methyl)benzyl)-4-(3,7-bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)butanamide (47);
m. N-(4-((4R,7R,10S,13S,19S,E)-7-((1H-Indol-2-yl)methyl)-4-(4-hydroxyphenyl)-8,13,15,19-tetramethyl-2,6,9,12-tetraoxo-1-oxa-5,8,11-triazacyclononadec-15-en-10-yl)butyl)-4-(3,7-bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)butanamide (49);
n. 4-(3,7-Bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)-N-(4-(4-(6-(4-methylpiperazin-1-yl)-1H,3′H-[2,5′-bibenzo[d]imidazol]-2′-yl)phenoxy)butyl)butanamide (51);
o. (2αR,4S,4αS,6R,9S,11S,12S,12αR,12βS)-12β-Acetoxy-9-((3-(4-(3,7-bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)butanamido)-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4α,8,13,13-tetramethyl-5-oxo-2α,3,4,4α,5,6,9,10,11,12,12α,12β-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-β]oxet-12-yl benzoate (53);
p. 8-(4-(3,7-Bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)butanamido)octanoic acid (55);
q. (2αR,4S,4αS,6R,9S,11S,12S,12αR,12βS)-12β-Acetoxy-9-((3-(8-(4-(3,7-bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)butanamido)octanamido)-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4α,8,13,13-tetramethyl-5-oxo-2α,3,4,4α,5,6,9,10,11,12,12α,12β-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-β]oxet-12-yl benzoate (56);
r. 4-(3,7-Bis(dimethylamino)-5,5-dimethyldibenzo[b,e]silin-10(5H)-ylidene)-N-(4-(6-methyl-1,2,4,5-tetrazin-3-yl)benzyl)butanamide (58);
s. 4-(3,7-Bis(dimethylamino)-5,5-diisopropyldibenzo[b,e]silin-10(5H)-ylidene)-N-(2-(2-((6-chlorohexyl)oxy)ethoxy)ethyl)butanamide (59);
t. 4-(3,7-Bis(dimethylamino)-5,5-diisopropyldibenzo[b,e]silin-10(5H)-ylidene)-N-(21-chloro-8-oxo-3,6,12,15-tetraoxa-9-azahenicosyl)butanamide (64);
u. 1-(4-(3,7-Bis(dimethylamino)-5,5-diisopropyldibenzo[b,e]silin-10(5H)-ylidene)butanamido)-N-(2-(2-((6-chlorohexyl)oxy)ethoxy)ethyl)-3,6,9,12-tetraoxapentadecan-15-amide (65);
v. N-(4-(((2-Amino-9H-purin-6-yl)oxy)methyl)benzyl)-4-(3,7-bis(dimethylamino)-5,5-diisopropyldibenzo[b,e]silin-10(5H)-ylidene)butanamide (66);
w. 3-((4-(((2-Amino-9H-purin-6-yl)oxy)methyl)benzyl)amino)-2-(4-(3,7-bis(dimethylamino)-5,5-diisopropyldibenzo[b,e]silin-10(5H)-ylidene)butanamido)-3-oxopropane-1-sulfonic acid (69);

20 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/956,596Filed 20 Dec 2018
Priority: EP 17209895.621 Dec 2017
Published: 11 May 2023
Term ends: Not estimatedThe source records don’t support an estimate.

Classification14 codes

C09B 11/28
Diaryl- or thriarylmethane dyes: pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
C07F 7/0816
Comprising a heterocyclic ring: said ring comprising Si as a ring atom
C09K 11/06
Luminescent materials, e.g. electroluminescent or chemiluminescent: containing organic luminescent materials
G01N 1/30
Preparing specimens for investigation including physical details of chemical methods covered elsewhere, e.g. G01N33/50, C12Q: staining;…

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Abstract

A compound characterized by general formula (100):

wherein
R1 and R6 are independently selected from hydrogen and fluorine, particularly R1 and R6 are hydrogen;
R2, R3, R4 and R5 independently of each other is selected from H, halogen, SO3H, CO2H, NO2, CO2R, SO2R (with R being selected from C1 to C4 unsubstituted alkyl) and an unsubstituted or substituted (particularly unsubstituted or halogen-, amino-, hydroxyl-, SO3H- and/or carboxyl substituted) moiety selected from C1-C20 alkyl, C3-C8 cycloalkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C7-C20 alkylaryl, phenyl and 5- or 6-membered ring heteroaryl, or a combination thereof;
R7 and R8 are independently selected from:
unsubstituted and substituted C1-C12 alkyl, C3-C8 cycloalkyl, C2-C12 alkylene, C2-C12 alkylyne and C7-C12 alkylaryl;
unsubstituted or substituted 5- or 6-ring aryl, particularly phenyl, particularly wherein R7 is selected from H and a substituted or unsubstituted alkyl, alkenyl, alkenyl, alkylary or aryl having x carbon atoms and R8 is selected from H and a substituted or unsubstituted alkyl, alkenyl, alkenyl, alkylary or aryl having y carbon atoms and the sum of x and y is between 0 and 12, more particularly between 0 and 10, even more particularly between 0 and 8, even more particularly between 0 and 6;
RN1, RN2, RN3 and RN4 are:
independently selected from H, unsubstituted and substituted C1-C8 alkyl, C3-C8 cycloalkyl, C1-C4 acyl, and C7-C12 alkylaryl, and unsubstituted phenyl or phenyl substituted by COOH—, COOR, CONR2, unsubstituted alkyl, halogen, O-alkyl, and/or NO2;
or
RN1 together with RN2, and/or RN3 together with RN4 are a C3, C4, C6 unsubstituted or substituted alkyl forming a 3-7 sized ring structure;
or
RN1 and/or RN3 are independently selected from H and unsubstituted and substituted C1-C8 alkyl, C3-C8 cycloalkyl, and C7-C12 alkylaryl, and RN2 together with R2 or R3, and/or RN4 together with R4 or R5, is an unsubstituted or substituted C2, C3 or C4 alkyl, or an unsubstituted or substituted C2, C3 or C4 N-, O-, S-, or Se-alkyl;
one of R9 and R19 is hydrogen and the other one is hydrogen or a saturated carbon atom connected to a moiety selected from H, halogen, SO3H, CO2H, NO2, CO2R, SO2R (with R being selected from C1 to C4 unsubstituted alkyl) and an unsubstituted or substituted (particularly unsubstituted or halogen-, amino-, hydroxyl-, SO3H— and/or carboxyl substituted) moiety selected from C1-C20 alkyl, C3-C8 cycloalkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C7-C20 alkylaryl, phenyl and 5- or 6-membered ring heteroaryl, or a combination thereof
and wherein optionally the compound is covalently linked to a binding moiety M via any of the substituents.

11 more elements

Facts

Application

16/956,596Filed 20 Dec 2018

Priority

EP 17209895.621 Dec 2017

Published

11 May 2023

Term ends

Not estimatedThe source records don’t support an estimate.

Classification14 codes

C09B 11/28
Diaryl- or thriarylmethane dyes: pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
C07F 7/0816
Comprising a heterocyclic ring: said ring comprising Si as a ring atom
C09K 11/06
Luminescent materials, e.g. electroluminescent or chemiluminescent: containing organic luminescent materials
G01N 1/30
Preparing specimens for investigation including physical details of chemical methods covered elsewhere, e.g. G01N33/50, C12Q: staining;…