Fluorogenic dyes for high sensitivity DNA detection
AssigneeLife Technologies Corporation
InventorsKyle GEE, Jongtae YANG
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Abstract
The present disclosure is directed to unsymmetrical cyanine dyes comprising a substituted benzazolium ring system linked by a methine bridge to a quinolinium ring that contains a heteroatom. Compounds of formula (I) are provided herein. The compounds can be useful for fluorescent detection or quantification of nucleic acids. Related methods, uses, and kits are disclosed.
Claims73
A compound of formula (I):
- wherein:
- Z− is a biologically acceptable counterion;
- X is S, O, Se, or NRN1, where RN1 is H or C1-6 alkyl;
- n is 0, 1, or 2;
- R1 is H or —O—C1-6 alkyl;
- R2 is C2-6 alkyl;
- R3 is —(CH2)mNRR′, or —(CH2)mN+RR′R″, wherein:
- m is 2-6,
- R and R′ are each independently a substituted or unsubstituted aryl or heteroaryl, or a substituted or unsubstituted C1-6 alkyl, and
- R″ is H, a substituted or unsubstituted aryl or heteroaryl, or a substituted or unsubstituted C1-6 alkyl;
- and
- R5 is an alkyl, alkenyl, polyalkenyl, alkynyl or polyalkynyl group having 1-6 carbons;
- a substituted or unsubstituted aryl or heteroaryl;
- or a substituted or unsubstituted cycloalkyl having 3-10 carbons;
- wherein if R3 is —(CH2)3—N(CH3)2 or —(CH2)3—N+(CH3)3, then R2 is ethyl or C4-6 alkyl.
The compound of any one of the preceding claims, wherein R2 is C1-4 alkyl.
The compound of any one of the preceding claims, wherein R3 is —(CH2)3—N(CH3)2.
The compound of any one of the preceding claims, wherein R5 is a substituted or unsubstituted aryl or heteroaryl;
- or a substituted or unsubstituted cycloalkyl having 3-10 carbons.
The compound of any one of the preceding claims, wherein Z− is a halide, sulfate, an alkanesulfonate, an arylsulfonate, phosphate, perchlorate, tetrafluoroborate, tetraarylboride, nitrate, or an anion of an aromatic or aliphatic carboxylic acid.
The compound of any one of the preceding claims, wherein X is S.
The compound of any one of the preceding claims, wherein n is 0.
The compound of any one of the preceding claims, which is a compound of formula (II):
Dependencies are inferred from the claim text.