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US 12,644,001 B2Granted
Fluorenyl cyanine dyes
AssigneeBiotium, Inc.
InventorsFei Mao, Wai-Yee Leung, Patrick Mcgarraugh
Life of this patent
Estimating the term…
Abstract
The present invention relates to fluorescent dyes in general. The present invention provides a wide range of fluorescent dyes and kits containing the same, which are applicable for labeling a variety of biomolecules, cells and microorganisms. The present invention also provides various methods of using the fluorescent dyes for research and development, forensic identification, environmental studies, diagnosis, prognosis, and/or treatment of disease conditions.
Claims47
A compound of Formula 1a or 1b:
- wherein:
- X1 is O, S, NR1 or CR2R3;
- R1, R2 and R3 are independently substituted or unsubstituted alkyl, (R)p—(L)q—, or R2 and R3 taken together form a 3-8 membered ring optionally substituted by (R)p-(L)q—;
- R4, R5, R6, and R7 are independently hydrogen, halo, —CN, alkoxy, alkyl, aryl, heteroaryl, amino, alkylamino, dialkylamino, alkanecarboxamido, alkanesulfonamido, aminocarbonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl, N,N,N-trialkylammoniumalkyl, aminosufonyl, N-alkylaminosulfonyl, N,N-dialkylaminosulfonyl, phosphonyl, carboxylate, azide, nitro, arylazo, or (R)p—(L)q—;
- at least one substituent pair of R4 and R5, R5 and R6, or R6 and R7, taken together with the atoms it is attached to, is a substituent pair forming a fused ring system according to Formula 1c:
- where the dashed lines represent the bonds of the substituent pair connecting to Formula 1a or 1b;
- R9 is halo, —CN, alkoxy, alkyl, aryl, heteroaryl, amino, alkylamino, dialkylamino, alkanecarboxamido, alkanesulfonamido, aminocarbonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl, N,N,N-trialkylammoniumalkyl, aminosufonyl, N-alkylaminosulfonyl, N,N-dialkylaminosulfonyl, phosphonyl, sulfonate, carboxylate, azide, nitro, arylazo, or (R)p—(L)q—;
- a is 0, 1, 2, 3, or 4;
- X2 is CR11R12, where each R11 and R12 is substituted or unsubstituted alkyl, (R)p—(L)q—, or R11 and R12 taken together form a 3-8 membered ring, optionally substituted by (R)p—(L)q—;
- Y is a bridge unit that permits electron delocalization optionally comprising (R)p—(L)q—;
- Q is optionally substituted aryl or heteroaryl;
- R8 is H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or (R)p—(L)q—;
- or
- R8 taken together with R7 forms a saturated or unsaturated 5- or 6-membered ring, optionally substituted;
- or
- R8, taken together with a substituent on the moiety Y, forms a 5- or 6-membered saturated or unsaturated ring;
- or
- R8, taken together with a substituent on the moiety Q, forms a macrocycle;
- W is a counter ion;
- c is an integer indicating the number of W such that the overall charge of Formula 1 is zero;
- each R of each (R)p—(L)q— substituent is independently i) a reactive group capable of forming a covalent bond upon reacting with a reaction substrate;
- ii) a water-soluble group;
- or iii) a biopolymer;
- each L of each R)p—(L)q— substituent is independently a linking moiety formed of one or more chemical bonds and containing about 1-100 atoms;
- each p of each R)p—(L)q— is independently an integer of about 1 to about 20;
- each q of each R)p—(L)q— is independently an integer of 0 to about 20;
- and
- the compound of Formula 1a or 1b comprises at least one substituent which is R)p—(L)q—.
25 more elements
A compound of Formula 3a or 3b:
- wherein:
- R2 and R3 are independently substituted or unsubstituted alkyl, (R)p—(L)q—, or R2 and R3 taken together form a 3-8 membered ring optionally substituted by (R)p—(L)q—;
- R4, and R7 are independently hydrogen, halo, —CN, alkoxy, alkyl, aryl, heteroaryl, amino, alkylamino, dialkylamino, alkanecarboxamido, alkanesulfonamido, aminocarbonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl, N,N,N-trialkylammoniumalkyl, aminosufonyl, N-alkylaminosulfonyl, N,N-dialkylaminosulfonyl, phosphonyl, carboxylate, azide, nitro, arylazo, or (R)p—(L)q—;
- R9 is halo, —CN, alkoxy, alkyl, aryl, heteroaryl, amino, alkylamino, dialkylamino, alkanecarboxamido, alkanesulfonamido, aminocarbonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl, N,N,N-trialkylammoniumalkyl, aminosufonyl, N-alkylaminosulfonyl, N,N-dialkylaminosulfonyl, phosphonyl, sulfonate, carboxylate, azide, nitro, arylazo, or (R)p—(L)q—;
- a is 0, 1, 2, 3, or 4;
- R8 is H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or (R)p—(L)q—;
- or
- R8 taken together with R7 forms a saturated or unsaturated 5-or 6-membered ring, optionally substituted;
- W is a counter ion;
- c is an integer indicating the number of W such that the overall charge of Formula 1 is zero;
- each R of each (R)p—(L)q— substituent is independently i) a reactive group capable of forming a covalent bond upon reacting with a reaction substrate;
- ii) a water-soluble group;
- or iii) a biopolymer;
- each L of each (R)p—(L)q— substituent is independently a linking moiety formed of one or more chemical bonds and containing about 1-100 atoms;
- each p of each (R)p—(L)q— is independently an integer of about 1 to about 20;
- each q of each (R)p—(L)q— is independently an integer of 0 to about 20;
- and
- the compound of Formula 3a or 3b comprises at least one substituent which is (R)p—(L)q—.
15 more elements
Dependencies are inferred from the claim text.