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US 2019/0241584 A1Published application
Fluorescent dye and preparation method and use thereof
AssigneeEast China University of Science and Technology
InventorsLinyong Zhu, Yi Yang, Dasheng Zhang, Zengmin Du, Bingkun Bao, Qiuning Lin, Yan Li, Xianjun Chen, Lipeng Yang, Chunyan Bao
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Abstract
Provided are a fluorescent dye and a preparation process and use thereof. The fluorescent dye is able to emit a long wavelength, is sensitive and specific to viscosity, and is used for a wide range of purposes, such as viscosity testing, fluorescent labeling, quantification or detection of proteins, enzymes or nucleic acids. In addition, it can be used as a fluorescent-activated probe.
Claims20
A fluorescent dye, having a structure represented by formula (I):
- wherein,
- D- is X0O— or N(X1)(X2)—;
- X0, X1, and X2 are each independently selected from the group consisting of hydrogen, an alkyl group and a modified alkyl group;
- X1 and X2 are optionally linked to each other to form a saturated or unsaturated alicyclic heterocyclic ring;
- the ring B is selected from at least one consisting of an aromatic ring and an aromatic heterocyclic ring;
- in the structure of the following formula (I-2) formed by condensing the ring B with a thiophene ring, each hydrogen atom contained therein is optionally replaced independently with a substituent selected from the group consisting of a halogen atom, a nitro group, a hydrophilic group, an alkyl group, and a modified alkyl group, the substituents being optionally linked to each other to form a saturated or unsaturated alicyclic or alicyclic heterocyclic ring;
- optionally, the structure of the formula (I-2) is interlinked to X1, X2 to form an alicyclic heterocyclic ring;
- R1 is selected from the group consisting of hydrogen, a halogen atom, a nitro group, an alkyl group, an aryl group, a heteroaryl group, a hydrophilic group, or a modified alkyl group;
- R2 is selected from the group consisting of cyano, carboxyl, a keto group, an ester group, an amide group, a phosphonic acid group, a phosphonate group, a sulfonic group, a sulfonate group, a sulfone group, a sulfoxide group, an aryl group, a heteroaryl group, an alkyl group, or a modified alkyl group;
- R3 is a cyano group;
- the structural moiety of the following formula (I-3) in the formula (I):
- optionally forms a cyclic structure of the following formulae (I-3-a) or (I-3-b):
- wherein, Ra and Rb are selected independently from the group consisting of hydrogen, an alkyl group, and a modified alkyl group, and Ra and Rb are optionally bonded to each other to form an alicyclic or alicyclic heterocyclic ring;
- Rc and Rd are selected independently from the group consisting of hydrogen, a halogen atom, nitro, an alkyl group, an aryl group, a hydrophilic group, and a modified alkyl group;
- Y1 is selected from the groups consisting of —O—, —S—, —(S═O)—, and —(NRi)—, wherein Ri is selected from the group consisting of hydrogen, an alkyl group, and a modified alkyl group;
- Y2 is selected from the group consisting of ═O, ═S, ═S═O, and ═NRi, wherein Ri is selected from the group consisting of hydrogen, an alkyl group, and a modified alkyl group;
- Y3 is selected from the group consisting of ═O, ═S, ═S═O, and ═NRi, wherein Ri is selected from the groups consisting of hydrogen, an alkyl group, and a modified alkyl group, or
- Y3 is ═C(Re)(CN);
- Re is selected from the group consisting of cyano, carboxyl, a keto group, an ester group, an amide group, a phosphonic acid group, a phosphonate group, a sulfonic group, a sulfonate group, a sulfone group, a sulfoxide group, an aryl group, a heteroaryl group, an alkyl group, or a modified alkyl group;
- when R2 or Re is an aryl group or a heteroaryl group, the hydrogen atom on the ring is optionally replaced independently with a substituent selected from the group consisting of a halogen atom, nitro, a hydrophilic group, an alkyl group or a modified alkyl group;
- optionally, the substituents being linked to each other to form a saturated or unsaturated alicyclic or alicyclic heterocyclic ring;
- wherein,
- the alkyl group is a saturated aliphatic linear or branched alkyl group having 1 to 10 carbon atoms;
- the modified alkyl group is a group obtained by replacing any carbon atom of the alkyl group with at least one group selected from the group consisting of a halogen atom, —O—, —OH, —CO—, —NO2, —CN, —S—, —SO2—, —(S═O)—,
- phenylene, a primary amino group, a secondary amino group, a tertiary amino group, a quaternary ammonium group, a saturated or unsaturated monocyclic or bicyclic cyclohydrocarbylene group, a bridged alicyclic heterocyclic ring;
- the modified alkyl group has 1 to 50 carbon atoms, wherein the carbon-carbon single bond is optionally replaced independently by a carbon-carbon double bond or a carbon-carbon tripe bond;
- the alicyclic ring is a four to ten-membered monocyclic or polycyclic alicyclic ring;
- the alicyclic heteroalicyclic ring is a four to ten-membered monocyclic or polycyclic alicyclic heteroalicyclic ring with at least one heteroatom selected from the group consisting of N, O, S and Si on the ring;
- when the alicyclic heteroalicyclic ring contains an S atom, it is optionally —SO— or —SO2—;
- the alicyclic heterocyclic ring is optionally substituted with a halogen atom, nitro, an alkyl group, an aryl group, a hydrophilic group, and a modified alkyl group;
- the aryl group or the aromatic ring is a five to ten-membered monocyclic or condensed bicyclic ring;
- the heteroaryl or the aromatic heterocyclic ring is a five to ten-membered monocyclic or condensed bicyclic ring with at least one heteroatom selected from the group consisting of N, O, S and Si on the ring;
- the halogen atoms are each independently selected from the group consisting of F, Cl, Br, and I;
- the hydrophilic group is hydroxyl, a sulfonic group, a sulphuric acid group, a phosphonic acid group, a primary amino group, a secondary amino group or a tertiary amino group and substituendum thereof;
- the monocyclic cyclohydrocarbylene group is a four to seven-membered monocyclic cyclohydrocarbylene group;
- the bicyclic cyclohydrocarbylene group is a five to seven-membered bicyclic cyclohydrocarbylene group;
- the bridged alicyclic heterocyclic ring is a five to twenty-membered bridged alicyclic heterocyclic ring having at least one heteroatom selected from the group consisting of N, O, and S on the ring.
34 more elements
Dependencies are inferred from the claim text.