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US 5,684,137 AGranted
S.sub.3 N chelating compounds for the radiolabeling of ligands, anti-ligands or other proteins
AssigneeNeoRx Corporation
InventorsSudhakar Kasina, Linda M. Gustavson
Life of this patent
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Abstract
Novel chelating compounds and the corresponding radionuclide metal chelates are useful for radiolabeling proteins such as antibodies, ligands such as biotin and anti-ligands such as streptavidin with radionuclide metals such as .sup.99m Tc, .sup.186 Re, and .sup.188 Re. The radiolabeled proteins, ligands and anti-ligands have diagnostic or therapeutic use, depending on the radionuclide metal chosen.
Claims17
A compound of the following formula:
- ##STR33## wherein:
- each R is a protecting group;
- Q is hydrogen or a protecting group;
- each T is selected from the group consisting of hydrogen, lower alkyl groups of from 1 to about 6 carbon atoms, electron withdrawing groups, and lower alkyl groups of from 1 to about 6 carbon atoms substituted with electron withdrawing group(s);
- each R' is selected from the group consisting of:
- --(CH.sub.2).sub.n --COOH with n=0 to about 4,
- --(CH.sub.2).sub.n --Z, wherein Z represents a ligand or an anti-ligand selected from the group consisting of avidin, streptavidin and biotin and, optionally further includes a conjungation group which provides for covalent attachment of the ligand or anti-ligand to the --(CH.sub.2).sub.n moiety and wherein n is 0 to about 4,
- hydrogen, and
- a lower alkyl group of from 1 to about 6 carbon atoms;
- each R" is selected from the group consisting of:
- --(CH.sub.2).sub.n --COOH with n=0 to about 4,
- hydrogen, and
- a lower alkyl group of from 1 to about 6 carbon atoms;
- and
- the compound comprises at least one --(CH.sub.2).sub.n --Z substituent.
12 more elements
A compound of the formula:
- ##STR35## wherein:
- each R is a protecting group;
- each T is selected from the group consisting of hydrogen, lower alkyl groups of from 1 to about 6 carbon atoms, electron withdrawing groups, and lower alkyl groups of from 1 to about 6 carbon atoms substituted with electron withdrawing group(s);
- X is O, S, or NH;
- each R' is selected from the group consisting of:
- --(CH.sub.2).sub.n --COOH with n=0 to about 4,
- --(CH.sub.2).sub.n --Z, wherein Z represents a ligand or anti-ligand selected from the group consisting of avidin, streptavidin and biotin and, optionally further includes a conjugation group which provides for the covalent attachment of the ligand or anti-ligand to the (CH.sub.2).sub.n group and wherein n is 0 to about 4,
- hydrogen, and
- a lower alkyl group of from 1 to about 6 carbon atoms;
- each R" is selected from the group consisting of:
- --(CH.sub.2).sub.n --COOH with n=0 to about 4,
- hydrogen, and
- a lower alkyl group of from 1 to about 6 carbon atoms;
- and
- the compound comprises at least one --(CH.sub.2).sub.n --Z substituent.
12 more elements
A radionuclide metal chelate-containing compound of the formula:
- ##STR37## wherein:
- M represents a radionuclide metal or oxide thereof;
- each T is selected from the group consisting of hydrogen, lower alkyl groups of from 1 to about 6 carbon atoms, electron withdrawing groups, and lower alkyl groups of from 1 to about 6 carbon atoms substituted with electron withdrawing group(s);
- each R' is selected from the group consisting of:
- --(CH.sub.2).sub.n --COOH with n=0 to about 4,
- --(CH.sub.2).sub.n --Z, wherein Z represents a ligand or an anti-ligand selected from the group consisting of avidin, streptavidin, and biotin and, optionally further includes a conjugation group which provides for the covalent attachment of the ligand or anti-ligand to the (CH.sub.2).sub.n group and wherein n is 0 to about 4,
- hydrogen, and
- a lower alkyl group of from 1 to about .sub.6 carbon atoms;
- each R" is selected from the group consisting of:
- --(CH.sub.2).sub.n --COOH with n=0 to about 4,
- hydrogen, and
- a lower alkyl group of from 1 to about 6 carbon atoms;
- and
- the compound comprises at least one --(CH.sub.2).sub.n --Z substituent.
11 more elements
A radionuclide metal chelate-containing compound of the formula:
- ##STR38## wherein:
- M represents a radionuclide metal or oxide thereof;
- each T is selected from the group consisting of hydrogen, lower alkyl groups of from 1 to about 6 carbon atoms, electron withdrawing groups, and lower alkyl groups of from 1 to about 6 carbon atoms substituted with electron withdrawing group(s);
- X represents O, S, or NH;
- each R' is selected from the group consisting of:
- --(CH.sub.2).sub.n --COOH with n=0 to about 4,
- --(CH.sub.2).sub.n --Z, wherein Z represents a ligand or an anti-ligand selected from the group consisting of avidin streptavidin and biotin and, optionally further includes a conjugation group which provides for the covalent attachment of the ligand or anti-ligand to the (CH.sub.2).sub.n and wherein n is 0 to about 4,
- hydrogen, and
- a lower alkyl group of from 1 to about 6 carbon atoms;
- each R" is selected from the group consisting of:
- --(CH.sub.2).sub.n --COOH with n=0 to about 4,
- hydrogen, and
- a lower alkyl group of from 1 to about 6 carbon atoms;
- and
- the compound comprises at least one --(CH.sub.2).sub.n --Z substituent.
12 more elements
An S.sub.3 N-biotin conjugate selected from the group consisting of N-methyl-N-4-biocytinamido-(S,S'-isopropylidene)-2,3-dimercapto!butyryl-S -benzyl cysteine;
- N-(5-biotinamido)-pentylamido!-S,S'-(isopropylidene)-2,3-dimercapto!buty ryl-S-benzyl cysteine;
- biocytinamido-(S-benzyl)-cysteinyl-S,S'-isopropylidene)-2,3-dimercaptosuc cinate;
- and (S-benzyl)-cysteinyl-5-biotinamido)-pentylamido!-(S,S'-isopropylidene)-2, 3-dimercaptosuccinate.
Dependencies are inferred from the claim text.