US2012004391A2PendingUtilityA2
Cyanine-type compounds having an alkynyl linker arm
Est. expiryAug 12, 2023(expired)· nominal 20-yr term from priority
Inventors:Giuseppe Caputo
C09B 23/083C07D 401/14C07F 5/022C07D 209/08C09B 23/06
43
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Claims
Abstract
Cyanine-type fluorescent dyes modified with an alkynyl linker arm of formula (I), suitable for the conjugation of biomolecules, such as for example nucleosides, nucleotides, oligonucleotides, nucleic acids, proteins, peptides, vitamins and hormones. A method and intermediates for the synthesis of the alkynyl cyanines of the invention are also described, as well as alkynyl cyanine-biomolecule conjugates and methods for preparing thereof. The alkynyl cyanines can be advantageously used as markers for biomolecules or as quenchers.
Claims
exact text as granted — not AI-modified1 - 10 . (canceled)
11 . A cyanine modified with an alkynyl-linker arm, having the following general formula (I), including the valence tautomers thereof:
wherein
R 1 is a linear alkyl chain having 4 carbon atoms;
W 1 and W 2 are independently selected from a benzene ring and a naphthalene ring;
X 1 and X 2 are independently selected from the group consisting of —O— and —C(CH 3 ) 2 ; R 2 is —R 8 —Y, wherein Y is selected from the group consisting of carboxyl, hydroxyl, amino, dinitrophenyl, —C≡CH, and succinimidyl ester, and wherein R 8 is a linear, saturated or unsaturated alkyl chain, having from 1 to 30 carbon atoms, wherein one or more carbon atoms are each optionally substituted by a component independently selected by an oxygen or a sulfur atom, a —NH— or a —CONH— group, or a cyclic 4-, 5- or 6-membered grouping of carbon atoms, aromatic or not aromatic, wherein one or more carbon atoms are each optionally substituted by a heteroatom independently selected from oxygen, sulfur, nitrogen or selenium;
R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of H, —SO 3 − , —NO 2 and CH 3 (—OCH 2 CH 2 ) n —O—;
M is a counterion; and
Q is a polymethinic chain selected from the group consisting of:
wherein R 7 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, phenoxy, thiophenoxy, anilino, cyclohexylamino, pyridine, —R 8 —Y, —O—R 8 —Y, —S—R 8 —Y, —NH—R 8 —Y, wherein R 8 and Y are as defined above, and aryl optionally substituted by one or more substituents independently selected from the group consisting of —SO 3 H, —COOH, —NH 2 , —CHO, —SCN, —CNS, epoxy and —COZ wherein Z represents a leaving group.
12 . The cyanine according to claim 11 , further comprising a second fluorescent dye, conjugated through the linker arm —R 1 —C≡CH, wherein said second fluorescent dye is a transition metal complex with at least one heterocyclic nitrogen-containing ligand.
13 . The cyanine according to claim 11 , wherein said second fluorescent dye is N,N′-Difluoroboryl-1,9-dimethyl-5-(4-iodophenyl)-dipyrrin.
14 . The cyanine according to claim 13 , wherein said second fluorescent dye emits fluorescence at wavelengths at which the cyanine absorbs, or said fluorescent dye absorbs at wavelengths at which the cyanine emits.
15 . The cyanine according to claim 11 , wherein X 1 and X 2 are ═C(CH 3 ) 2 , and W 1 and W 2 are a naphthalene ring.
16 . The cyanine according to claim 15 , wherein R 3 and R 4 are —SO 3 − or —NO 2 , and R 5 and R 6 are H.
17 . The cyanine according to claim 16 , selected from the group consisting of
18 . The cyanine according to claim 15 , wherein R 3 , R 4 , R 5 and R 6 are —SO 3 − .
19 . The cyanine according to claim 15 , selected from the group consisting of
20 . The cyanine according to claim 15 , wherein R 3 , R 4 and one of R 5 and R 6 are —SO 3 − , and the other of R 5 and R 6 is H.
21 . The cyanine according to claim 20 , selected from the group consisting of
22 . The cyanine according to claim 15 , wherein R 3 , R 4 , R 5 and R 6 are H.
23 . The cyanine according to claim 22 , selected from the group consisting of
24 . The cyanine according to claim 11 , wherein X 1 and X 2 are ═C(CH 3 ) 2 , one of W 1 and W 2 is a benzene ring and the other of W 1 and W 2 is a naphthalene ring, and R 3 , R 4 , R 5 , and R 6 are H.
25 . The cyanine according to claim 24 , selected from the group consisting of
26 . The cyanine according to claim 11 wherein X 1 and X 2 are ═C(CH 3 ) 2 , W 1 and W 2 are benzene ring, and R 3 , R 4 , R 5 , and R 6 are independently selected from H and —SO 3 − .
27 . The cyanine according to claim 26 , selected from the group consisting of
28 . The cyanine according to claim 11 , wherein X 1 and X 2 are —O—, W 1 and W 2 are a benzene ring, R 3 , R 4 , R 5 , and R 6 are H, and Y is —C≡CH.
29 . The cyanine according to claim 28 , consisting of
30 . The cyanine according to claim 11 , selected from the group consisting ofJoin the waitlist — get patent alerts
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