New fluorescent cyanine labels containing a sulfamido linker...

C - Chemistry – Metallurgy – 09 – B

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C09B 23/12 (2006.01) C07H 19/04 (2006.01) C07H 21/00 (2006.01) C09B 23/06 (2006.01) C09B 23/08 (2006.01) C09K 11/06 (2006.01) G01N 33/533 (2006.01) G01N 33/58 (2006.01)

Patent

CA 2312099

A fluorescent cyanine dye of the following general formula is disclosed: (see above formula) wherein: X1 and X2 are independently selected from the group consisting of -O-, -S-, - C(CH3)2- and -C(=CH2)-; Y1 and Y2 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; R1 and R2 are independently selected from the group consisting of H, C1-C4, alkyl, alkylensulfonic group or alkylensulfonate group wherein the alkylene group has from 1 to 4 carbon atoms; R3, R4 and R5 are independently selected from the group consisting of H, a sulfonic group, a sulfonate group, alkylensulfonic, alkylensulfonate and -SO2NH(CH2)m-W-(CH2)n Z, wherein alkylene has 1 to 4 carbon atoms, with the proviso that at least one of R1 to R5 contains a sulfonic or sulfonate group; W is absent or is a group selected from -SO2NH, -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 .noteq. 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 -NH2, -OH, and -SH groups; groups capable of reacting with such functionalities include -COCl, -COOCOR, -CONHNH2, N- hydroxysuccinimido esters, -NCS, -CHO, -COCH2I, phosphoramidite and maleimido.

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