US 2014/0273043 A1Published application

Tri-color dual glucose and oxygen sensors and methods of preparing and using them

AssigneeArizona Board of Regents, A Body Corporate of the State of Arizona Acting for and On Behalf of Arizona State University

InventorsYanqing Tian, Liqiang Zhang, Fengyu Su, Deirdre Meldrum, Sean Buizer

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Abstract

The present disclosure relates to an optical fluorescence sensor comprising a probe for sensing glucose, an intra-reference probe, and a matrix. The present disclosure also relates to an optical fluorescence dual sensor comprising a probe for sensing glucose, a probe for sensing oxygen, an intra-reference probe, and a matrix. The present disclosure additionally relates to methods of preparing these sensors and methods of using them.

Claims25

Dependent claims

An optical fluorescence sensor comprising:

(a) a probe for sensing glucose having formula I:
wherein R1 and R2 can be the same or different and are CnH2n+1, where n is an integer selected from the group consisting of 0, 1, 2, 3, 4, 5, 6, 7 and 8;
R3 is selected from the group consisting of (CH2)nC(O)OH, O(CH2)nC(O)OH, NH(CH2)nC(O)OH, (CH2)nC(O)OR4, O(CH2)nC(O)OR4, NH(CH2)nC(O)OR4, (CH2)nC(O)NH(CH2)nNH-A, O(CH2)nC(O)NH(CH2)nNH-A, NH(CH2)nC(O)NH(CH2)nNH-A, (CH2)nC(O)O(CH2)nNH-A, O(CH2)nC(O)O(CH2)nNH-A, NH(CH2)nC(O)O(CH2)nNH-A, (CH2)nC(O)NH(CH2)nNH-M′A, O(CH2)nC(O)NH(CH2)nNH-M′A, NH(CH2)nC(O)NH(CH2)nNH-M′A. (CH2)nC(O)O(CH2)nNH-M′A, O(CH2)nC(O)O(CH2)nNH-M′A, NH(CH2)nC(O)O(CH2)nNH-M′A, (CH2)nC(O)NH(CH2)nNH-VA, O(CH2)nC(O)NH(CH2)nNH-VA, NH(CH2)nC(O)NH(CH2)nNH-VA, (CH2)nC(O)O(CH2)nNH-VA, (CH2)nC(O)O(CH2)nNH-VA, NH(CH2)nC(O)O(CH2)nNH-VA;
n is an integer selected from the group of consisting of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12;
R4 is an activating group;
M′A is
A is
and
VA is
(b) an intra-reference probe having formula III:
wherein R15, R16, R17, and R18 can be the same or different and are CnH2n+1, where n is an integer selected from the group consisting of 1, 2, 3, 4. 5, 6, 7 and 8;
X is an anion;
and
Z is selected from the group consisting of:
(CH2)pOH, O(CH2)pOH, NH(CH2)pOH, (CH2)pOM′A, O(CH2)pOM′A, NH(CH2)pOM′A, (CH2)pOA, O(CH2)pOA, NH(CH2)pOA, (CH2)pOVA, O(CH2)pOVA, NH(CH2)pVA, (OCH2CH2)qOH, NH(CH2CH2O)qH, (OCH2CH2)qOM′A, NH(CH2CH2O)qM′A, (OCH2CH2)qOA, NH(CH2CH2O)qA, (OCH2CH2)qOVA, NH(CH2CH2O)qVA, CH2(OCH2CH2)rOA, CH2(OCH2CH2)rOM′A, CH2(OCH2CH2)rOVA;
and
r is an integer selected from the group of consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 38, 39, 40, 41, 42, 43, 44, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149 and 150;
and
(c) a matrix comprising a polymer selected from the group consisting of acrylamide, N-(6-aminohexyl)methacrylamide, and poly(ethylene glycol) dimethacrylate, methoxy-poly(ethylene glycol) methacrylate, 2-hydroxyethyl methacrylate and combinations thereof;
wherein the probes are attached to or immobilized in the matrix.

17 more elements

An optical fluorescence dual sensor comprising:

(a) a probe for sensing glucose having formula I:
wherein R1 and R2 can be the same or different and are CnH2n+1, where n is an integer selected from the group consisting of 0, 1, 2, 3, 4, 5, 6, 7 and 8;
R3 is selected from the group consisting of (CH2)mC(O)OH, O(CH2)mC(O)OH, NH(CH2)mC(O)OH, (CH2)mC(O)OR4, O(CH2)mC(O)OR4, NH(CH2)mC(O)OR4, (CH2)mC(O)NH(CH2)mNH-A, O(CH2)mC(O)NH(CH2)mNH-A, NH(CH2)mC(O)NH(CH2)mNH-A, (CH2)mC(O)O(CH2)mNH-A O(CH2)mC(O)O(CH2)mNH-A, NH(CH2)mC(O)O(CH2)mNH-A, (CH2)mC(O)NH(CH2)mNH-M′A, O(CH2)mC(O)NH(CH2)mNH-M′A, NH(CH2)mC(O)NH(CH2)mNH-M′A, (CH2)mC(O)O(CH2)mNH-M′A, O(CH2)mC(O)O(CH2)mNH-M′A, NH(CH2)mC(O)O(CH2)mNH-M′A, (CH2)mC(O)NH(CH2)mNH-VA, O(CH2)mC(O)NH(CH2)mNH-VA, NH(CH2)mC(O)NH(CH2)mNH-VA, (CH2)mC(O)O(CH2)mNH-VA, O(CH2)mC(O)O(CH2)mNH-VA, NH(CH2)mC(O)O(CH2)mNH-VA;
m is an integer selected from the group of consisting of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12;
R4 is an activating group;
M′A is
A is
VA is
(b) a probe for sensing oxygen having formula II:
wherein M is selected from Pt or Pd;
R11 and R12 can be the same or different and are independently selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3 and OC2Hs,
R13 and R14 can be the same or different and are independently selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3 and OC2H5;
R5 and R6 can be the same or different and are independently selected from the group consisting of H, F, Cl, Br, I, CH3, OCH3 and OC2H5;
R7, R8, R9 and R10 can be the same or different and are independently selected from the group consisting of (CH2)pOH, O(CH2)pOH, NH(CH2)pOH, (CH2)pOM′A, O(CH2)pOM′A, NH(CH2)pOM′A, (CH2)pOA, O(CH2)pOA, NH(CH2)pOA, (CH2)pOVA, O(CH2)pOVA, NH(CH2)pOVA, (OCH2CH2)qOH, NH(CH2CH2O)qH, (OCH2CH2)qOM′A, NH(CH2CH2O)qM′A, (OCH2CH2)qOA, NH(CH2CH2O)qA, (OCH2CH2)qOVA, NH(CH2CH2O)qVA,
where
p is an integer selected from the group of consisting of 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12,
q is an integer selected from the group of consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 38, 39, 40, 41, 42, 43, 44, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149 and 150;
(c) an intra-reference probe having formula III:
wherein R15, R16, R17, and R18 can be the same or different and are CnH2n+1, where n is an integer selected from the group consisting of 1, 2, 3, 4, 5, 6, 7 and 8;
X is an anion;
and
Z is selected from the group consisting of:
(CH2)pOH, O(CH2)pOH. NH(CH2)pOH, (CH2)pOM′A, O(CH2)pOM′A, NH(CH2)pOM′A, (CH2)pOA, O(CH2)pOA, NH(CH2)pOA, (CH2)pOVA, O(CH2)pOVA, NH(CH2)pOVA, (OCH2CH2)qOH, NH(CH2CH2O)qH, (OCH2CH2)qOM′A, NH(CH2CH2O)qM′A, (OCH2CH2)qOA, NH(CH2CH2O)qA, (OCH2CH2)qOVA, NH(CH2CH2O)qVA, CH2(OCH2CH2)rOA, CH2(OCH2CH2)rOM′A, CH2(OCH2CH2)rOVA;
and
r is an integer selected from the group of consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 38, 39, 40, 41, 42, 43, 44, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149 and 150;
and
(d) a matrix comprising a polymer selected from the group consisting of acrylamide, 6-aminohexyl methacrylamide, and poly(ethylene glycol) dimethacrylate, methoxy-poly(ethylene glycol) methacrylate, 2-hydroxyethyl methacrylate and combinations thereof.
wherein the probes are attached to or immobilized in the matrix.

25 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/210,357Filed 13 Mar 2014
Priority: 14 Mar 2013
Published: 18 Sep 2014
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

G01N 33/66
Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing:…
C12Q 1/54
Measuring or testing processes involving enzymes, nucleic acids or microorganisms ; Compositions therefor; Processes of preparing such…
G01N 21/6486
Fluorescence; Phosphorescence: measuring fluorescence of biological material, e.g. DNA, RNA, cells
G01N 33/582
Involving labelled substances: with fluorescent label

Family

Application61/786,046Us provisional application · filed 14 Mar 2013
US 10,156,573 B2Related patent
US 2014/0273043 A1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

An optical fluorescence sensor comprising:

(a) a probe for sensing glucose having formula I:
wherein R1 and R2 can be the same or different and are CnH2n+1, where n is an integer selected from the group consisting of 0, 1, 2, 3, 4, 5, 6, 7 and 8;
R3 is selected from the group consisting of (CH2)nC(O)OH, O(CH2)nC(O)OH, NH(CH2)nC(O)OH, (CH2)nC(O)OR4, O(CH2)nC(O)OR4, NH(CH2)nC(O)OR4, (CH2)nC(O)NH(CH2)nNH-A, O(CH2)nC(O)NH(CH2)nNH-A, NH(CH2)nC(O)NH(CH2)nNH-A, (CH2)nC(O)O(CH2)nNH-A, O(CH2)nC(O)O(CH2)nNH-A, NH(CH2)nC(O)O(CH2)nNH-A, (CH2)nC(O)NH(CH2)nNH-M′A, O(CH2)nC(O)NH(CH2)nNH-M′A, NH(CH2)nC(O)NH(CH2)nNH-M′A. (CH2)nC(O)O(CH2)nNH-M′A, O(CH2)nC(O)O(CH2)nNH-M′A, NH(CH2)nC(O)O(CH2)nNH-M′A, (CH2)nC(O)NH(CH2)nNH-VA, O(CH2)nC(O)NH(CH2)nNH-VA, NH(CH2)nC(O)NH(CH2)nNH-VA, (CH2)nC(O)O(CH2)nNH-VA, (CH2)nC(O)O(CH2)nNH-VA, NH(CH2)nC(O)O(CH2)nNH-VA;
n is an integer selected from the group of consisting of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12;
R4 is an activating group;
M′A is
A is
and
VA is
(b) an intra-reference probe having formula III:
wherein R15, R16, R17, and R18 can be the same or different and are CnH2n+1, where n is an integer selected from the group consisting of 1, 2, 3, 4. 5, 6, 7 and 8;
X is an anion;
and
Z is selected from the group consisting of:
(CH2)pOH, O(CH2)pOH, NH(CH2)pOH, (CH2)pOM′A, O(CH2)pOM′A, NH(CH2)pOM′A, (CH2)pOA, O(CH2)pOA, NH(CH2)pOA, (CH2)pOVA, O(CH2)pOVA, NH(CH2)pVA, (OCH2CH2)qOH, NH(CH2CH2O)qH, (OCH2CH2)qOM′A, NH(CH2CH2O)qM′A, (OCH2CH2)qOA, NH(CH2CH2O)qA, (OCH2CH2)qOVA, NH(CH2CH2O)qVA, CH2(OCH2CH2)rOA, CH2(OCH2CH2)rOM′A, CH2(OCH2CH2)rOVA;
and
r is an integer selected from the group of consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 38, 39, 40, 41, 42, 43, 44, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149 and 150;
and
(c) a matrix comprising a polymer selected from the group consisting of acrylamide, N-(6-aminohexyl)methacrylamide, and poly(ethylene glycol) dimethacrylate, methoxy-poly(ethylene glycol) methacrylate, 2-hydroxyethyl methacrylate and combinations thereof;
wherein the probes are attached to or immobilized in the matrix.

17 more elements

Facts

Application

14/210,357Filed 13 Mar 2014

Priority

14 Mar 2013

Published

18 Sep 2014

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

G01N 33/66
Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing:…
C12Q 1/54
Measuring or testing processes involving enzymes, nucleic acids or microorganisms ; Compositions therefor; Processes of preparing such…
G01N 21/6486
Fluorescence; Phosphorescence: measuring fluorescence of biological material, e.g. DNA, RNA, cells
G01N 33/582
Involving labelled substances: with fluorescent label