Sulfonyl cyanine dyes and derivatives
AssigneeCombinix, Inc.
InventorNicholas Cairns
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Abstract
Fluorescent cyanine and squaraine dyes are described that can be conjugated to analyte molecules of interest such as peptides, proteins, nucleic acids, RNA, DNA, carbohydrates, polymers and small molecules via a sulfonyl or sulfonamide substituent. The new dyes are made via a novel cyanine dye activation procedure that converts the normally stable, water solubilizing sulfonate substituents into a reactive sulfonyl halides. The sulfonyl halides may be directly conjugated to analytes or can be further converted to more stable reactive sulfonamide handles or to water soluble sulfonamides. The general structure of the new dyes is given below where the central linker is an unsaturated carbon chain or an unsaturated chain containing a squaraine moiety.
Claims10
A composition of matter comprising a fluorescent compound
- wherein:
- m is 1 or 2;
- A is independently selected from the group consisting of O, Se, Te and CR2 wherein,
- R is independently selected from the group consisting of Me, Et, C3-C16 alkyl, alkyl ether groups and oligo ethylene glycol groups containing 2 to 20 oxygen atoms;
- Z is independently selected from the group consisting of Me, Et, and C3-C16 alkyl;
- L is independently selected from the group consisting of F, Cl, Br, O-aryl,
- —NH—(Y)—NR2 and —NH—(Y)—NR—CO—(Y)—COT wherein,
- Y is selected from the group consisting of a C1-C18 alkyl chain, an ether linkage, an aromatic linkage, C1-C12 cycloalkyl and an oligoethylene glycol linkage containing 2 to 20 oxygen atoms,
- R in this instance is independently selected from the group consisting of H, Me, Et, and C3-C16 alkyl;
- and wherein T is independently selected from the group consisting of OH, Cl, Br, O—(C1-C16) alkyl, O-aryl, N-hydroxysuccinimide ester, hydroxybenzotriazole ester, haloalkylacetamide, —NH-maleimide, thiocyanate, cyanate, phosphoramidite, symmetrical anhydrides and unsymmetrical acid anhydrides.
A composition of matter comprising
- wherein:
- m is 1, 2 or 3;
- A is independently selected from the group consisting of O and CMe2;
- Z is independently selected from the group consisting of Me, Et, and C3-C12 alkyl;
- R in this instance is independently selected from the group consisting of H, Me, Et, and C3-C16 alkyl.
Dependencies are inferred from the claim text.