Fluorescent acridinium salts, synthesis thereof and use for detection of cardiolipin
The present invention relates to a novel substituted acridinium salts as fluorescent dyes, as well as methods of their manufacturing and use of the disclosed compounds for the detection of cardiolipin.
1 . A compound of Formula I:
wherein
R represents C 1-6 -alkylene-silyl(C 1-3 -alkyl) 3 ; and
X − represents chloride, bromide, or iodide.
2 . The compound of claim 1 , wherein the compound has the structure:
3 . A process for the synthesis of a compound of Formula I:
wherein:
R represents C 1-15 alkyl, C 1-3 deuterated alkyl, or C 1-6 -alkylene-silyl(C 1-3 -alkyl) 3 ; and
X − represents chloride, bromide, or iodide;
comprising reacting a compound 1:
with C 1-12 alkyl halide, C 1-3 deuterated alkyl halide, or C 1-6 -alkylene-silyl(C 1-3 -alkyl) 3 halide in the presence of potassium phosphate.
4 . The compound of claim 1 , wherein R is C 1-3 -alkylene-silyl(C 1-3 -alkyl) 3 .
5 . The compound of claim 4 , wherein R is (CH 2 ) 3 —Si(CH 3 ) 3 .
6 . The compound of claim 5 , wherein X − is iodide.
7 . The process of claim 3 , wherein R is C 1-12 alkyl, deuterated methyl, or C 1-3 -alkylene-silyl(C 1-3 -alkyl) 3 .
8 . The process of claim 7 , wherein R is CH 3 , CD 3 , C 9 H 19 , C 12 H 25 , or (CH 2 ) 3 —Si(CH 3 ) 3 .
9 . The process of claim 8 , wherein X − is iodide.
10 . A method of detecting cardiolipin comprising contacting the compound of claim 1 with cardiolipin.
11 . The method of claim 10 , further comprising detecting a loss in fluorescence intensity.