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US 2023/0257587 A1Published application
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.
Claims48
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 O, S, NR10, SiR11R12, or CR11R12, where each R10, R1 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;
- 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- of R1 or R2 is independently an integer of 0 to about 20;
- and
- the compound of Formula 1 comprises at least one substituent which is (R)p-(L)q-.
25 more elements
The compound of any of the preceding claims, where R8, taken together with a substituent on the moiety Q, forms a macrocycle.
The compound of any preceding claim, wherein R8 is not methyl.
The compound of any preceding claim, wherein the compound is:
The compound of any preceding claim, wherein the compound has an absorption maximum equal to or greater than about 660 nm.
The compound of any preceding claim, wherein the compound has an absorption maximum of between about 660 and about 1250 nm.
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- of R1 or R2 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.