N-heteroaromatic ion and iminium ion substituted cyanine dyes for use as fluorescence labels
First Claim
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1. A cyanine dye having the formula ##STR27## wherein n and m are each independently either 0, 1, 2 or 3;
- R1 and R2 are taken together to form an aromatic ring or a fused polycyclic aromatic ring;
R3 and R4 are taken together to form an aromatic ring or a fused polycyclic aromatic ring;
R5 and R6 are independently selected from the group consisting of (CH2)p X where p is 1-18 and X is a functional group that reacts with amino, hydroxy or sulfhydryl nucleophiles;
R7 and R8 are independently selected from the group consisting of hydrogen, C1-C10 alkyl groups and where R7 and R8 are taken together to form a five- or six- membered heterocyclic ring;
R9 are each independently selected from the group consisting of hydrogen, alkyl and where more than one R9 are taken together to form a five- or six- membered ring;
Y is selected from the group consisting of C(CH3)2 and S; and
Z is selected from the group consisting of C(CH3)2 and S.
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Abstract
The present invention relates to iminium ion substituted cyanine dyes having a fluoresence absorbance of between about 500 and 900 nm, a reduced tendency to aggregate and enhanced photostability. The cyanine dyes of the present invention are represented by the formula ##STR1## wherein n is 0, 1, 2 or 3;
m is 0, 1, 2 or 3;
R1 and R2 are taken together to form an aromatic ring or a fused polycyclic aromatic ring;
R3 and R4 are taken together to form an aromatic ring or a fused polycyclic aromatic ring;
R5 and R6 are independently selected from the group consisting of (CH2)p X where p is 1-18 and X is a functional group that reacts with amino, hydroxyl and sulfhydryl nucleophiles;
R7 and R8 are independently selected from the group consisting of hydrogen, C1-C10 alkyl groups and where R7 and R8 are taken together to form a five- or six- membered heterocyclic ring;
R9 are each independently selected from the group consisting of hydrogen, alkyl and where more than one R9 are taken together to form a five- or six- membered ring;
Y is selected from the group consisting of C(CH3)2, S, O and Se; and
Z is selected from the group consisting of C(CH3)2, S, O and Se.
139 Citations
36 Claims
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1. A cyanine dye having the formula ##STR27## wherein n and m are each independently either 0, 1, 2 or 3;
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R1 and R2 are taken together to form an aromatic ring or a fused polycyclic aromatic ring; R3 and R4 are taken together to form an aromatic ring or a fused polycyclic aromatic ring; R5 and R6 are independently selected from the group consisting of (CH2)p X where p is 1-18 and X is a functional group that reacts with amino, hydroxy or sulfhydryl nucleophiles; R7 and R8 are independently selected from the group consisting of hydrogen, C1-C10 alkyl groups and where R7 and R8 are taken together to form a five- or six- membered heterocyclic ring; R9 are each independently selected from the group consisting of hydrogen, alkyl and where more than one R9 are taken together to form a five- or six- membered ring; Y is selected from the group consisting of C(CH3)2 and S; and Z is selected from the group consisting of C(CH3)2 and S. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
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11. A cyanine dye having the formula ##STR28## wherein r is 1, 2 or 3;
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R1 and R2 are taken together to form an aromatic ring or a fused polycyclic aromatic ring; R3 and R4 are taken together to form an aromatic ring or a fused polycyclic aromatic ring; R5 and R6 are independently selected from the group consisting of (CH2)p X where p is 1-18 and X is a functional group that reacts with amino, hydroxy or sulfhydryl nucleophiles; R7 and R8 are independently selected from the group consisting of hydrogen, C1-C10 alkyl and where R7 and R8 are taken together to form a five- or six- membered heterocyclic ring; Y is selected from the group consisting of C(CH3)2 and S; and Z is selected from the group consisting of C(CH3)2 and S. - View Dependent Claims (12, 13, 14, 15, 16, 17, 18)
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19. A cyanine dye selected from the group consisting of:
- ##STR29##
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20. Method for fluorescent labeling a molecule comprising:
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labeling a molecule having an amino, hydroxy or sulfhydryl functional group with a cyanine dye having the formula ##STR30## wherein n and m are each independently either 0, 1, 2 or 3; R1 and R2 are taken together to form an aromatic ring or a fused polycyclic aromatic ring; R3 and R4 are taken together to form an aromatic ring or a fused polycyclic aromatic ring; R5 and R6 are independently selected from the group consisting of (CH2)p X where p is 1-18 and X is a functional group that reacts with amino, hydroxy or sulfhydryl nucleophiles; R7 and R8 are independently selected from the group consisting of hydrogen, C1-C10 alkyl and where R7 and R8 are taken together to form a five- or six- membered heterocyclic ring; R9 are each independently selected from the group consisting of hydrogen, alkyl and where more than one R9 are taken together to form a five- or six- membered ring; Y is selected from the group consisting of C(CH3)2 and S; and Z is selected from the group consisting of C(CH3)2 and S. - View Dependent Claims (21, 22, 23, 24, 25, 26, 27)
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28. Method for fluorescent labeling a molecule comprising:
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labeling a molecule having an amino, hydroxy or sulfhydryl functional group with a cyanine dye having the formula ##STR31## wherein r is 1, 2 or 3; R1 and R2 are taken together to form an aromatic ring or a fused polycyclic aromatic ring; R3 and R4 are taken together to form an aromatic ring or a fused polycyclic aromatic ring; R5 and R6 are independently selected from the group consisting of (CH2)p X where p is 1-18 and X is a functional group that reacts with amino, hydroxy or sulfhydryl nucleophiles; R7 and R8 are independently selected from the group consisting of hydrogen, C1-C10 alkyl and where R7 and R8 are taken together to form a five- or six- membered heterocyclic ring; Y is selected from the group consisting of C(CH3)2 and S; and Z is selected from the group consisting of C(CH3)2 and S. - View Dependent Claims (29, 30, 31, 32, 33, 34, 35)
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36. Method for fluorescent labeling a molecule comprising:
labeling a molecule having an amino, hydroxy or sulfhydryl functional group with a cyanine dye selected from the group consisting of;
##STR32##
Specification
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Current AssigneeBiometric Imaging, Inc. (Becton, Dickinson & Co)
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Original AssigneeBiometric Imaging, Inc. (Becton, Dickinson & Co)
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InventorsLee, Linda G., Woo, Sam L.
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Primary Examiner(s)Higel, Floyd D.
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Application NumberUS08/268,852Time in Patent Office453 DaysField of Search546/273, 530/802, 548/312.1, 548/427, 544/124, 536/24.3, 536/24.31, 536/24.32, 536/25.32, 435/968, 435/4, 435/7.8, 436/538, 436/542, 436/172, 436/800US Class Current544/124CPC Class CodesA61K 49/0032 Methine dyes, e.g. cyanine ...C09B 23/0041 the substituent being bound...C09B 23/0066 the polymethine chain being...C09B 23/02 the polymethine chain conta...G01N 33/533 with fluorescent labelY10S 435/968 High energy substrates, e.g...Y10S 436/80 Fluorescent dyes, e.g. rhod...Y10S 530/802 Chromogenic or luminescent ...
