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US 11,597,969 B2Granted
Cyclooctatetraene containing dyes and compositions
AssigneeIllumina Cambridge Limited
InventorsXiaolin Wu, Xiaohai Liu, Nikolai Nikolaevich Romanov, Antoine Francais, Patrick McCauley, Michael Callingham, Carole Anastasi
Life of this patent
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Abstract
Embodiments of the present disclosure relate to cyclooctatetraene containing dyes and their uses as fluorescent labels. Also provided are composition containing cyclooctatetraene. The dyes and compositions may be used in various biological applications, such as nucleic acid sequencing.
Claims20
A fluorescent compound comprising a photo-protecting cyclooctatetraene moiety, wherein the photo-protecting cyclooctatetraene moiety comprises the structure of formula (I):
- wherein:
- each of R1 and R2 are each independently selected from the group consisting of H, hydroxyl, halogen, azido, thiol, nitro, cyano, unsubstituted and substituted amino, carboxyl, —C(O)OR5, —C(O)NR6R7, unsubstituted and substituted C1-6 alkyl, unsubstituted and substituted C1-6 alkoxy, unsubstituted and substituted C1-6 haloalkyl, unsubstituted and substituted C1-6 haloalkoxy, unsubstituted and substituted C2-6 alkenyl, unsubstituted and substituted C2-6 alkynyl, unsubstituted and substituted C6-10 aryl, unsubstituted and substituted C7-14 aralkyl, unsubstituted and substituted C3-7 carbocyclyl, unsubstituted and substituted 5 to 10 membered heteroaryl, and unsubstituted and substituted 3 to 10 membered heterocyclyl;
- X is —C(═O)—NR4;
- Y is selected from the group consisting of —O—, —S—, —NR3—, —C(═O)—, —C(═O)—O—, —C(═O)—NR4—, —S(O)2—, —NR3—C(═O)—NR4, —NR3—C(═S)—NR4—, and unsubstituted and substituted heteroalkylene where at least one carbon atom is replaced with O, S, or N;
- Z is absent, unsubstituted or substituted C2-6 alkenylene, or unsubstituted or substituted C2-6 alkynylene;
- each of R3 and R4 is independently H, unsubstituted or substituted C1-6 alkyl, or unsubstituted or substituted C6-10 aryl;
- R5 is unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C6-10 aryl, unsubstituted or substituted C7-14 aralkyl, unsubstituted or substituted C3-7 carbocyclyl, unsubstituted or substituted 5 to 10 membered heteroaryl, or unsubstituted or substituted 3 to 10 membered heterocyclyl;
- each of R6 and R7 is independently H, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C6-10 aryl, unsubstituted or substituted C7-14 aralkyl, unsubstituted or substituted C3-7 carbocyclyl, unsubstituted or substituted 5 to 10 membered heteroaryl, or unsubstituted or substituted 3 to 10 membered heterocyclyl;
- the carbon atom to which R1 and R2 are attached in
- is optionally replaced with O, S, or N, provided that when said carbon atom is replaced with O or S, then R1 and R2 are both absent;
- when said carbon atom is replaced with N, then R2 is absent;
- and
- m is an integral number between 1 and 10;
- provided that the fluorescent compound is not a cyanine dye, and wherein the fluorescent compound is excitable by a light source having a wavelength between about 350 nm to about 500 nm.
11 more elements
Dependencies are inferred from the claim text.