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US 2008/0305489 A1Published application
Near-infrared dyes as surface enhanced raman scattering reporters
AssigneeBecton, Dickinson and Company
InventorsJoseph Thomas, Rajendra R. Bhat, W. Shannon Dillmore, Douglas B. Sherman
Life of this patent
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Abstract
Nanoparticles comprising surface-enhanced Raman scattering (SERS) reporter molecules of the formula A-Y and methods of their use are disclosed, wherein A is selected from the group consisting of: wherein X1 is CR4 or N; and Y is selected from the group consisting of:
Claims48
A nanoparticle comprising a SERS-active reporter molecule of the formula:
- A-Y
- wherein:
- A is selected from the group consisting of:
- wherein X1 is CR4 or N;
- Y is selected from the group consisting of:
- wherein:
- r, s, and t are each independently an integer from 1 to 8;
- each X2 and X3 is independently selected from the group consisting of C, S, and N, under the proviso that (i) when X2 is C or S, R5 is Z, or when X3 is C or S, R6 is Z, as Z is defined herein below;
- (ii) if both X2 and X3 are N at the same time, at least one of R5 and R6 is absent;
- and (iii) when X2 is N, R5 when present is Z′, or when X3 is N, R6 when present is Z′, wherein Z′ is selected from the group consisting of:
- —(CH2)n—X4;
- —NR8—(CH2)p—X5;
- —(CH2)qX6C(═O)—R9,
- wherein:
- n, p, q, u, and v are each independently an integer from 1 to 8;
- X4 and X5 are each independently selected from the group consisting of hydroxyl, amino, and thiol;
- X6 is O or NR11;
- wherein:
- each R1, R2, R3, R4, R5, R6, R8, R10, R11, and Z is independently selected from the group consisting of H, alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, aryl, substituted aryl, aralkyl, hydroxyl, alkoxyl, hydroxyalkyl, hydroxycycloalkyl, alkoxycycloalkyl, aminoalkyl, acyloxyl, alkylaminoalkyl, and alkoxycarbonyl;
- R7 is Z′;
- R9 is —(CH2)m—X7 or —(CH2)m—B, wherein
- m is an integer from 1 to 8;
- X7 is halogen;
- and
- B is a binding member having a binding affinity for a ligand or analyte to be detected.
22 more elements
The nanoparticle of 12, wherein the glass comprises SiOx.
A method for labeling a molecule, cell, bead, or solid support, the method comprising:
- (a) providing at least one of a molecule, cell, bead, or solid support;
- and
- (b) attaching a particle to the at least one of a molecule, cell, bead, or solid support, wherein the particle comprises a surface-enhanced Raman spectroscopy (SERS)-active nanoparticle having associated therewith a dye of Formula:
- A-Y
- wherein:
- A is selected from the group consisting of:
- wherein X1 is CR4 or N;
- Y is selected from the group consisting of:
- wherein:
- r, s, and t are each independently an integer from 1 to 8;
- each X2 and X3 is independently selected from the group consisting of C, S, and N, under the proviso that (i) when X2 is C or S, R5 is Z, or when X3 is C or S, R6 is Z, as Z is defined herein below;
- (ii) if both X2 and X3 are N at the same time, at least one of R5 and R6 is absent;
- and (iii) when X2 is N, R5 when present is Z′, or when X3 is N, R6 when present is Z′, wherein Z′ is selected from the group consisting of:
- —(CH2)n—X4;
- —NR8—(CH2)p—X5;
- —(CH2)qX6C(═O)—R9,
- wherein:
- n, p, q, u, and v are each independently an integer from 1 to 8;
- X4 and X5 are each independently selected from the group consisting of hydroxyl, amino, and thiol;
- X6 is O or NR11;
- wherein:
- each R1, R2, R3, R4, R5, R6, R8, R10, R11, and Z is independently selected from the group consisting of H, alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, aryl, substituted aryl, aralkyl, hydroxyl, alkoxyl, hydroxyalkyl, hydroxycycloalkyl, alkoxycycloalkyl, aminoalkyl, acyloxyl, alkylaminoalkyl, and alkoxycarbonyl;
- R7 is Z′;
- R9 is —(CH2)m—X7 or —(CH2)m—B, wherein
- m is an integer from 1 to 8;
- X7 is halogen;
- and
- B is a binding member having a binding affinity for a ligand or analyte to be detected.
25 more elements
A method for detecting the presence or amount of one or more analytes in a biological sample, the method comprising:
- (a) providing a biological sample suspected of containing one or more analytes;
- (b) contacting the biological sample with a reagent comprising one or more SERS-active nanoparticles having associated therewith at least one specific binding member having an affinity for the one or more analytes and at least one SERS-active reporter molecule of Formula:
- A-Y
- wherein:
- A is selected from the group consisting of:
- wherein X1 is CR4 or N;
- Y is selected from the group consisting of:
- wherein:
- r, s, and t are each independently an integer from 1 to 8;
- each X2 and X3 is independently selected from the group consisting of C, S, and N, under the proviso that (i) when X2 is C or S, R5 is Z, or when X3 is C or S, R6 is Z, as Z is defined herein below;
- (ii) if both X2 and X3 are N at the same time, at least one of R5 and R6 is absent;
- and (iii) when X2 is N, R5 when present is Z′, or when X3 is N, R6 when present is Z′, wherein Z′ is selected from the group consisting of:
- —(CH2)n—X4;
- —NR8—(CH2)p—X5;
- —(CH2)qX6C(═O)—R9,
- wherein:
- n, p, q, u, and v are each independently an integer from 1 to 8;
- X4 and X5 are each independently selected from the group consisting of hydroxyl, amino, and thiol;
- X6 is O or NR11;
- wherein:
- each R1, R2, R3, R4, R5, R6, R8, R10, R11, and Z is independently selected from the group consisting of H, alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, aryl, substituted aryl, aralkyl, hydroxyl, alkoxyl, hydroxyalkyl, hydroxycycloalkyl, alkoxycycloalkyl, aminoalkyl, acyloxyl, alkylaminoalkyl, and alkoxycarbonyl;
- R7 is Z′;
- R9 is —(CH2)m—X7 or —(CH2)m—B, wherein
- m is an integer from 1 to 8;
- X7 is halogen;
- and
- B is a binding member having a binding affinity for a ligand or analyte to be detected;
- (c) illuminating the biological sample with incident radiation at a wavelength to induce the SERS-active reporter molecule to produce a SERS signal;
- and
- (d) measuring the SERS signal to detect the presence or amount of one or more analytes in the biological sample.
27 more elements
A kit comprising a reagent comprising one or more surface-enhanced Raman spectroscopy (SERS)-active nanoparticles having associated therewith at least one SERS-active reporter molecule of Formula:
- A-Y
- wherein:
- A is selected from the group consisting of:
- wherein X1 is CR4 or N;
- Y is selected from the group consisting of:
- wherein:
- r, s, and t are each independently an integer from 1 to 8;
- each X2 and X3 is independently selected from the group consisting of C, S, and N, under the proviso that (i) when X2 is C or S, R5 is Z, or when X3 is C or S, R6 is Z, as Z is defined herein below;
- (ii) if both X2 and X3 are N at the same time, at least one of R5 and R6 is absent;
- and (iii) when X2 is N, R5 when present is Z′, or when X3 is N, R6 when present is Z′, wherein Z′ is selected from the group consisting of:
- —(CH2)n—X4;
- —NR8—(CH2)p—X5;
- —(CH2)qX6C(═O)—R9,
- wherein:
- n, p, q, u, and v are each independently an integer from 1 to 8;
- X4 and X5 are each independently selected from the group consisting of hydroxyl, amino, and thiol;
- X6 is O or NR11;
- wherein:
- each R1, R2, R3, R4, R5, R6, R8, R10, R11, and Z is independently selected from the group consisting of H, alkyl, substituted alkyl, heteroalkyl, substituted heteroalkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, aryl, substituted aryl, aralkyl, hydroxyl, alkoxyl, hydroxyalkyl, hydroxycycloalkyl, alkoxycycloalkyl, aminoalkyl, acyloxyl, alkylaminoalkyl, and alkoxycarbonyl;
- R7 is Z′;
- R9 is —(CH2)m—X7 or —(CH2)m—B, wherein
- m is an integer from 1 to 8;
- X7 is halogen;
- and
- B is a binding member having a binding affinity for a ligand or analyte to be detected.
22 more elements
Dependencies are inferred from the claim text.