US2012214184A1PendingUtilityA1
Doxorubicin immunoassay
Est. expiryMar 30, 2025(expired)· nominal 20-yr term from priority
G01N 33/9446C07K 16/44G01N 33/94Y10S530/807A61K 47/646
57
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Claims
Abstract
Novel conjugates of doxorubicin and novel doxorubicin immunogens derived from the 13 and 14 positions of doxorubicin and antibodies generated by these doxorubicin linked immunogens all of which are useful in immunoassays for the quantification and monitoring of doxorubicin in biological fluids.
Claims
exact text as granted — not AI-modified1 . A compound of the formula:
wherein A is
Y is an organic spacing group;
X is a functional group capable of binding to a thiol or amino group; and
p is an integer from 0 to 1.
2 . The compound of claim 1 , wherein X is
wherein R 3 is hydrogen or taken together with its attached oxygen atom forms a reactive ester and R 4 is oxygen or sulfur.
3 . The compound of claim 2 , wherein X is
and R 3 is hydrogen.
4 . The compound of claim 2 , wherein X is
and R 3 forms a reactive ester.
5 . The compound of claim 4 , wherein the ester formed is a lower alkyl ester, imidoester or amidoester.
6 . The compound of claim 1 , wherein X is a functional group capable of binding to a thiol group.
7 . The compound of claim 6 , wherein X is
8 . The compound of claim 7 , wherein Y is alkylene containing from 1 to 10 carbon atoms.
9 . A compound of the formula:
wherein Y is an organic spacing group;
X is a functional group capable of binding to a thiol or an amino group; and
B is —CH 2 — or
or mixtures thereof.
10 . The compound of claim 9 , wherein p is 0.
11 . The compound of claim 10 , wherein X is
wherein R 3 is hydrogen or taken together with its attached oxygen atom forms a reactive ester and R 4 is oxygen or sulfur.
12 . The compound of claim 11 , wherein X is
and R 3 is hydrogen.
13 . The compound of claim 12 , wherein X is
and R 3 forms a reactive ester.
14 . The compound of claim 13 , wherein the ester formed is a lower alkyl ester, imidoester or amidoester.
15 . The compound of claim 9 , wherein p is 1.
16 . The compound of claim 15 , wherein X is
wherein R 3 is hydrogen or taken together with its attached oxygen atom forms a reactive ester and R 4 is oxygen or sulfur.
17 . The compound of claim 16 , wherein Y is alkylene containing from 1 to 10 carbon atoms,
wherein n and o are integers from 0 to 6, and m is an integer from 1 to 6.
18 . A conjugate of a carrier containing a functional thiol or amino group with a compound of the formula:
wherein A is
Y is an organic spacing group;
X is a functional group capable of binding to said thiol or amino group;
and
p is an integer from 0 to 1.
19 . The conjugate of claim 18 , wherein p is 0.
20 . The conjugate of claim 19 , wherein X is
wherein R 3 is hydrogen or taken together with its attached oxygen atom forms a reactive ester and R 4 is oxygen or sulfur.
21 . The conjugate of claim 18 , wherein p is 1 and Y is alkylene containing from 1 to 10 carbon atoms,
wherein n and o are integers from 0 to 6, and m is an integer from 1 to 6.
22 . The conjugate of claim 21 , wherein said carrier has a reactive functional thiol group and X is a functional group capable of binding to said thiol group.
23 . The conjugate of claim 22 , wherein X is
24 . The conjugate of claim 23 , wherein Y is lower alkylene.
25 . The conjugate of claim 24 , wherein said carrier contains a polymeric polyamine containing a functional group of the formula:
wherein v is an integer from 1 to 6.
26 . A conjugate of a carrier having a thiol or amine group with a compound of the formula:
wherein B is —CH 2 — or
Y is an organic spacing group;
X is a functional group capable of binding to said thiol or amino group in said carrier; and
p is an integer from 0 to 1.
27 . The conjugate of claim 26 , wherein p is 0.
28 . The conjugate of claim 26 , wherein p is 1.
29 . The conjugate of claim 28 , wherein Y is alkylene containing from 1 to 10 carbon atoms,
wherein n and o are integers from 0 to 6, and m is an integer from 1 to 6.
30 . The conjugate of claim 29 , wherein the carrier contains an immunogenic polymeric polymer containing more amino groups linked by
wherein R 4 is oxygen or sulfur.
31 . A kit for determining the presence of doxorubicin in a patient sample comprising reagents in separate containers, one of the reagents being a conjugate of a carrier containing a functional amino or thiol group with a compound selected from the groups consisting of compounds of the formula:
wherein A is
Y is an organic spacing group;
X is a functional group capable of binding to the amino or thiol group in said carrier;
p is an integer from 0 to 1; and
or a 14-substituted doxorubicin of the formula:
wherein X, Y and p are as above and B is —CH 2 — or
or mixtures thereof; and the second container containing an antibody substantially selectively reactive with doxorubicin and not substantially cross-reactive to doxorubicin aglycone.
32 . The kit of claim 31 , wherein said conjugate is present in a predetermined amount in said first container.
33 . The kit of claim 32 , wherein said kit is used to determine the amount of doxorubicin in said sample.
34 . The kit of claim 31 , wherein, said antibody is generated from a conjugate of immunogenic carrier having a terminal functional amino or thiol group linked to said 13-substituted or 14-substituted doxorubicin.
35 . The kit of claim 34 , wherein said conjugate is said 13-substituted doxorubicin.
36 . The kit of claim 35 , wherein said carrier has a reactive terminal functional thiol group and X is a terminal functional group capable of binding to said thiol group.
37 . The kit of claim 36 , wherein X isCited by (0)
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