EP1065250A1 — New fluorescent cyanine labels containing a sulfamido linker arm

USPTO Abstract

A fluorescent cyanine dye of the following general formula is disclosed: wherein: X 1 and X 2 are indipendently selected from the group consisting of -O-, -S-, -C(CH 3 ) 2 or -C=CH 2 ; Y 1 and Y 2 are nonmetal atoms required to form a benzo-condensed or naphtho-condensed ring; Q is a conjugated moiety that increases the fluorescent quantum yield and the stability of the compound; R 1 and R 2 are indipendently selected from the group consisting of H, C 1 -C 4 , alkyl, alkylensulfonic group or alkylensulfonate group wherein the alkylene group has from 1 to 4 carbon atoms; R3, R4 and R5 are indipendently selected from the group consisting of H, a sulfonic group, a sulfonate group, alkylensulfonic, alkylensulfonate and -SO 2 NH(CH 2 ) m -W-CH 2 ) n Z, wherein alkylene has 1 to 4 carbon atoms, with the proviso that at least one of R 1 to R 5 contains a sulfonic or sulfonate group; W is absent or is a group selected from -SO 2 NH, -O-, -COO-, or -CONH-; n = 0-12 and m = 0-12 with the provisoes that m+n ≤ 12 and at least one of m and n ≠ 0; and Z is, or contains a N, O or S nucleophile functionality or is, or contains a functionality capable of reacting with N, O or S nucleophiles. Nucleophile functionalities include -NH 2 , -OH, and -SH groups; groups capable of reacting with such functionalities include -COCI, -COOCOR, -CONHNH 2 , N-hydroxysuccinimido esters, -NCS, -CHO, -COCH 2 I, phosphoramidite and maleimido.