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Details for Patent: 5,866,097

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Details for Patent: 5,866,097

Title: Technetium-99m labeled peptides for imaging
Abstract:The invention relates to radiolabeled imaging of a mammalian body. The invention in particular provides for reagents labeled with technetium-99m for such imaging. The invention provides peptides which bind Tc-99m and which can be targeted to specific sites within a mammalian body.
Inventor(s): Dean; Richard T. (Bedford, NH), McBride; William (Manchester, NH), Buttram; Scott (Derry, NH)
Assignee: Diatide, Inc. (Londonderry, NH)
Filing Date:Oct 28, 1994
Application Number:08/244,336
Claims:1. A peptide reagent for preparing a scintigraphic imaging agent for imaging target sites within a mammalian body, the reagent comprising a peptide comprised of between 4 and 100 amino acid residues that is covalently linked to a radiolabel complexing moiety comprising a single thiol-containing group having the formula:

wherein

A is H, HOOC, H.sub.2 NOC, (amino acid or peptide)-NHOC, (amino acid or peptide)-OOC or R.sup.4 ;

B is H, SH, --NHR.sup.3, --N(R.sup.3)-(amino acid or peptide), or R.sup.4 ;

X is H, SH, --NHR.sup.3, --N(R.sup.3)-(amino acid or peptide) or R.sup.4 ;

Z is H or R.sup.4 ;

R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently H or lower straight or branched chain or cyclic alkyl;

n is 0, 1 or 2;

and

where B is --NHR.sup.3 or --N(R.sup.3)-(amino acid or peptide), X is SH, and n is 1 or 2;

where X is --NHR.sup.3 or --N(R.sup.3)-(amino acid or peptide), B is SH, and n is 1 or 2;

where B is H or R.sup.4, A is HOOC, H.sub.2 NOC, (amino acid or peptide)-NHOC, (amino acid or peptide)-OOC, X is SH, and n is 0 or 1;

where A is H or R.sup.4, then where B is SH, X is --NHR.sup.3 or --N(R)-(amino acid or peptide) and where X is SH, B is --NHR.sup.3 or --N(R.sup.3)-(amino acid or peptide), wherein that X and B are not both SH;

where X is H or R.sup.4, A is HOOC, H.sub.2 NOC, (amino acid or peptide)-NHOC, (amino acid or peptide)-OOC and B is SH;

where Z is methyl, X is methyl, A is HOOC, H.sub.2 NOC, (amino acid or peptide)-NHOC, (amino acid or peptide)-OOC, B is SH and n is 0;

and wherein the thiol moiety is in the reduced form.

2. The peptide reagent according to claim 1 wherein the peptide and the radiolabel complexing moiety are covalently linked through one or more amino acids.

3. The peptide reagent according to claim 1 wherein the radiolabel complexing moiety is bound to technetium-99m a radioactive isotope.

4. A complex formed by reacting a peptide reagent according to claim 1 with Tc-99m in the presence of a reducing agent.

5. The complex of claim 4, wherein the reducing agent is selected from the group of a dithionite ion, a stannous ion, or a solid-phase reducing agent.

6. A complex formed by labeling a peptide reagent according to claim 1 with Tc-99m by ligand exchange of a prereduced Tc-99m complex.

7. A composition of matter comprising the peptide reagent according to claim 1 and a stannous ion.

8. A kit for preparing a radiopharmaceutical preparation, said kit comprising sealed vial containing a predetermined quantity of a peptide reagent according to claim 1 and a sufficient amount of reducing agent to label said reagent with Tc-99m.

9. A method for labeling a peptide reagent according to claim 1 comprising reacting the reagent with Tc-99m in the presence of a reducing agent.

10. The method of claim 9, wherein the reducing agent is selected from the group of a dithionite ion, a stannous ion, or a solid-phase reducing agent.

11. A method for imaging a target site within a mammalian body comprising administering an effective diagnostic amount of a scintigraphic imaging agent prepared by radiolabeling the peptide reagent according to claim 1 with Tc-99m wherein the scintigraphic imaging agent binds to the target site, and detecting the localized Tc-99m.

12. The peptide reagent according to claim 1 wherein the peptide is chemically synthesized in vitro.

13. The peptide reagent according to claim 12 wherein the peptide is synthesized by solid phase peptide synthesis.

14. The peptide reagent according to claim 12 wherein the complexing group is covalently linked to the peptide during in vitro chemical synthesis.

15. The peptide reagent according to claim 13 wherein the complexing group is covalently linked to the peptide during solid phase peptide synthesis.

16. A peptide according to claim 1 having the formula:
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