Xanthylium dyes that are well retained in mitochondria

Claim 1

A compound of the formula ##STR13## or of the formula ##STR14## wherein a fused-ring system has ring substituents R 1 , R 4 , R 5 , and R 8 are independently H, Cl, Br, I, (CH 2 ) n CH 3 , or (CH 2 ) n CO 2 R 13 , where n is an integer from 0 to 15 and R 13 is an alkyl with 1-6 carbons; and amino substituents R 2 , R 3 , R 6 , and R 7 that are independently H or C 1 -C 6 alkyl; or optionally any ring substituent in combination with an adjacent amino substituent independently forms an additional fused ring such that R 1 in combination with R 2 , R 3 in combination with R 4 , R 5 in combination with R 6 , and R 7 in combination with R 8 is (CH 2 ) 3 or (CH 2 ) 2 ; Ω is a single covalent bond or Ω is --Z--Y--where Z is attached to the fused ring system, and Z is a covalent bond, or Z is (CH 2 ) i where i=1-6, or Z is ##STR15## where R 11 is a hydrocarbon chain with 1-6 carbons that is branched, unbranched, saturated or unsaturated; Y is a covalent bond or Y has the formula --OCH 2 R 12 --, --OR 13 --, --SR 12 --, --SR 13 --, --NHCOCH 2 R 12 --, --NHCOR 13 --, --CONHCH 2 R 12 --, --CONHR 13 --, --NHSO 2 R 12 --, --NHSO 2 R 13 --, --NHCONHCH 2 R 12 --, --NHCONHR 13 --, --NHCSNHCH 2 R 12 --, or --NHCSNHR 13 --, where R 12 is (CH 2 ) m and m=1-18, and R 13 is phenylene (--C 6 H 4 --); such that Z and Y are not both covalent bonds; A is an alkylating group that is CR 9 R 10 X, where R 9 and R 10 are independently H or CH 3 , and X is Cl, Br, I, or --OSO 2 R 16 , where R 16 is C 1 -C 6 alkyl; C 1 -C 6 perfluoroalkyl; or R 16 is phenyl, or phenyl substituted one or more times by C 1 -C 6 alkyl, C 1 -C 6 perfluoroalkyl, Cl, Br, I, NO 2 , or CN; or the alkylating group A is maleimidyl (--NC 4 H 2 O 2 ) or haloacetamido (--NH(C═O)--CH 2 ) where is Cl, Br or I; and Ψ is a biologically compatible counterion.