Fluorescent dyes containing fused tetracyclic bis-boron heterocycle and uses in sequencing
AssigneeIllumina, Inc.
InventorsMichael Callingham, Justyna Piekos, Francesca Manni
Life of this patent
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Abstract
The present application relates to dyes containing fused tetracyclic bis-boron containing heterocycle and their uses as fluorescent labels. These dyes may be used as fluorescent labels for nucleotides in nucleic acid sequencing applications.
Claims43
A compound of Formula (I):
- a salt or a mesomeric form thereof, wherein each of R1, R2, R3, R6, R7 and R8 is independently H, unsubstituted or substituted C1-C6 alkyl, C1-C6 alkoxy, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 hydroxyalkyl, (C1-C6 alkoxy)(C1-C6 alkyl), unsubstituted or substituted amino, halo, cyano, carboxyl, hydroxy, nitro, sulfonyl, sulfino, sulfo, sulfonate, S-sulfonamido, N-sulfonamido, —C(═O)NR9 R10, —X—R11, unsubstituted or substituted C3-C10carbocyclyl, unsubstituted or substituted C6-C10 aryl, unsubstituted or substituted 5 to 10 membered heteroaryl, or unsubstituted or substituted 3 to 10 membered heterocyclyl;
- each of R4 and R5 is independently H, unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C3-C10 carbocyclyl, unsubstituted or substituted C6-C10 aryl, unsubstituted or substituted 5 to 10 membered heteroaryl, or unsubstituted or substituted 3 to 10 membered heterocyclyl;
- each of R9 and R10 is independently H, or unsubstituted or substituted C1-C6 alkyl;
- X is —O—, —S—, CH═CH— or —C≡C—;
- each of R11 is independently unsubstituted or substituted C3-C10 carbocyclyl, unsubstituted or substituted C6-C10 aryl, unsubstituted or substituted 5 to 10 membered heteroaryl, or unsubstituted or substituted 3 to 10 membered heterocyclyl;
- each of Ra, Rb, Rc and Rd is independently halo, cyano, unsubstituted C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, unsubstituted or substituted C6-C10 aryl, unsubstituted or substituted C6-C10 aryloxy, or —OC(═O)R12;
- R12 is unsubstituted or substituted C1-C6 alkyl, unsubstituted or substituted C2-C6 alkenyl, unsubstituted or substituted C6-C10 aryl, or unsubstituted or substituted 5 to 10 membered heteroaryl;
- alternatively, when both Ra and Rb are —OC(═O)R12, the two R12 together with the atoms to which they are attached form an unsubstituted or substituted 6 to 10 membered heterocyclyl;
- alternatively, when both Rc and Rd are —OC(═O)R12, the two R12 together with the atoms to which they are attached form an unsubstituted or substituted 6 to 10 membered heterocyclyl;
- and
- provided that at least one of R1, R2, R3, R4, R5, R6, R7 and R8 comprises a carboxyl group.
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An oligonucleotide or polynucleotide comprising the labeled nucleotide according to claim 30 incorporated thereto. (Currently Amended) The oligonucleotide or polynucleotide of claim 34, wherein the oligonucleotide or polynucleotide is at least partially complementary and hybridized to a target polynucleotide immobilized on a surface of a solid support, and wherein the solid support comprises an array of a plurality of immobilized target polynucleotides.
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Dependencies are inferred from the claim text.