PHOTOSTABLE DETECTABLE COMPOUNDS
Disclosed herein, inter alia, are detectable compounds including a triplet state quencher and the method of use thereof.
1 . A compound having the formula:
wherein
R 1 is a fluorescent dye moiety;
R 2 is independently halogen, —CCl 3 , —CBr 3 , —CF 3 , —CI 3 , —CHCl 2 , —CHBr 2 ,
—CHF 2 , —CHI 2 , —CH 2 Cl, —CH 2 Br, —CH 2 F, —CH 2 I, —CN, —OH, —NH 2 , —COOH, —CONH 2 , —NO 2 ,
—SH, —SO 3 H, —SO 4 H, —SO 2 NH 2 , —NHNH 2 , —ONH 2 , —NHC(O)NHNH 2 , —NHC(O)NH 2 ,
—NHSO 2 H, —NHC(O)H, —NHC(O)OH, —NHOH, —OCCl 3 , —OCF 3 , —OCBr 3 , —OCI 3 , —OCHCl 2 ,
—OCHBr 2 , —OCHI 2 , —OCHF 2 , —OCH 2 Cl, —OCH 2 Br, —OCH 2 I, —OCH 2 F, —N 3 , —SF 5 , —SO 2 C 1 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; and
z2 is an integer from 0 to 7;
R 3 is a bioconjugate reactive moiety;
W 1 is —O—, —NR 1A —, or —S—;
W 2 is —O—, —NR 2A —, or —S—;
R 1A and R 2A are independently hydrogen or substituted or unsubstituted alkyl; and
L 1 and L 2 are covalent linkers.
2 . The compound of claim 1 , wherein L 1 is L 101 -L 102 -L 103 ; wherein
L 101 , L 102 , and L 103 are independently a bond, —C(O)O—, —NHC(O)—, —C(O)NH—, substituted or unsubstituted alkylene, substituted or unsubstituted heteroalkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted heterocycloalkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene.
3 . The compound of claim 1 , wherein L 1 is
wherein n1 is an integer from 1 to 10.
4 . The compound of claim 1 , wherein L 2 is L 201 -L 202 -L 203 ; wherein L 201 , L 202 , and L 203 are independently a bond, —C(O)O—, —NHC(O)—, —C(O)NH—, substituted or unsubstituted alkylene, substituted or unsubstituted heteroalkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted heterocycloalkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene.
5 . The compound of claim 1 , wherein L 2 is
wherein n2 is an integer from 1 to 10.
6 . The compound of claim 1 , wherein W 1 is —NH—.
7 . The compound of claim 1 , wherein W 2 is —NH—.
8 . The compound of claim 1 , wherein —W 1 -L 1 is
9 . The compound of claim 1 , wherein —W 2 -L 2 is
10 . The compound of claim 1 , wherein R 3 is —N 3 , —NH 2 , —CN, —COOH,
11 . The compound of claim 1 , wherein R 1 is a rhodamine moiety, fluorescein moiety, triarylmethane moiety, cyanine moiety, fluorescein isothiocyanate moiety, indocyanine green moiety, coumarin moiety, or sulforhodamine 101 moiety.
12 . The compound of claim 1 , having the formula:
wherein n1 and n2 are independently an integer from 1 to 10.
13 . The compound of claim 1 , having the formula:
14 . The compound of claim 1 , having the formula:
15 . The compound of claim 1 , having the formula:
16 . A biomolecule covalently attached to a detectable label, wherein said detectable label has the formula:
wherein
R 1 is a fluorescent dye moiety;
R 2 is independently halogen, —CCl 3 , —CBr 3 , —CF 3 , —CI 3 , —CHCl 2 , —CHBr 2 ,
—CHF 2 , —CHI 2 , —CH 2 Cl, —CH 2 Br, —CH 2 F, —CH 2 I, —CN, —OH, —NH 2 , —COOH, —CONH 2 , —NO 2 ,
—SH, —SO 3 H, —SO 4 H, —SO 2 NH 2 , —NHNH 2 , —ONH 2 , —NHC(O)NHNH 2 , —NHC(O)NH 2 ,
—NHSO 2 H, —NHC(O)H, —NHC(O)OH, —NHOH, —OCCl 3 , —OCF 3 , —OCBr 3 , —OCI 3 , —OCHCl 2 ,
—OCHBr 2 , —OCHI 2 , —OCHF 2 , —OCH 2 Cl, —OCH 2 Br, —OCH 2 I, —OCH 2 F, —N 3 , —SF 5 , —SO 2 C 1 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl;
z2 is an integer from 0 to 7;
W 1 is —O—, —NR 1A —, or —S—;
W 2 is —O—, —NR 2A —, or —S—;
R 1A and R 2A are independently hydrogen or substituted or unsubstituted alkyl; and
L 1 and L 2 are covalent linkers.
17 . A method of imaging a biomolecule, said method comprising directing an excitation beam onto a biomolecule comprising a detectable moiety and detecting a light emission from said detectable moiety, wherein said biomolecule is the biomolecule of claim 16 .
18 . A kit comprising the compound of claim 1 .