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Details for Patent: 5,993,775

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Details for Patent: 5,993,775

Title: Radioactively labeled peptides comprising a single thiol moiety
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 technetium-99m, rhenium-186, or rhenium-188 and which can be targeted to specific sites within a mammalian body.
Inventor(s): Dean; Richard T. (Bedford, NH)
Assignee: Diatide, Inc. (Londonderry, NH)
Filing Date:Sep 28, 1998
Application Number:09/162,195
Claims:1. A peptide comprising between 7 and 100 amino acid residues, said peptide including a targeting amino acid sequence covalently linked to a technetium or rhenium complexing sequence through less than twenty amino acids, wherein the complexing sequence comprises a single thiol moiety having a structure:

wherein

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

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

Z is H or methyl;

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

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

n is 0, 1 or 2;

peptide represents the remaining components of the complexing sequence;

and wherein

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

where X is --NHR.sup.3 or --N(R.sup.3)-(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, (peptide)-NHOC, (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.sup.3)-(peptide) and where

X is SH, B is --NHR.sup.3 or --N(R.sup.3)-(peptide);

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

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

2. The peptide of claim 1, wherein the targeting sequence and the complexing sequence are linked through less than 15 amino acids.

3. The peptide of claim 1, wherein the targeting sequence and the complexing sequence are linked through less than 10 amino acids.

4. A pharmaceutical composition comprising the peptide of claim 1 and a pharmaceutically acceptable carrier.

5. A pharmaceutical composition comprising the peptide of claim 2 and a pharmaceutically acceptable carrier.

6. A pharmaceutical composition comprising the peptide of claim 3 and a pharmaceutically acceptable carrier.

7. The pharmaceutical composition of claim 4, further comprising technetium-99m.

8. The pharmaceutical composition of claim 5, further comprising technetium-99m.

9. The pharmaceutical composition of claim 6, further comprising technetium-99m.

10. The pharmaceutical composition of claim 4, further comprising rhenium-186 or rhenium-188.

11. The pharmaceutical composition of claim 5, further comprising rhenium-.sup.186 or rhenium-188.

12. The pharmaceutical composition of claim 6, further comprising rhenium-186 or rhenium-188.

13. A kit comprising a sealed vial containing a predetermined amount of the peptide of claim 1 and a sufficient amount of a reducing agent to label the peptide with technetium-99m, rhenium-186, or rhenium-188.

14. A kit comprising a sealed vial containing a predetermined amount of the peptide of claim 2 and a sufficient amount of a reducing agent to label the peptide with technetium-99m, rhenium-186, or rhenium-188.

15. A kit comprising a sealed vial containing a predetermined amount of the peptide of claim 3 and a sufficient amount of a reducing agent to label the peptide with technetium-99m, rhenium-186, or rhenium-188.

16. A technetium-99m complex of the peptide of claim 1.

17. A technetium-99m complex of the peptide of claim 2.

18. A technetium-99m complex of the peptide of claim 3.

19. A rhenium-186 or rhenium-188 complex of the peptide of claim 1.

20. A rhenium-186 or rhenium-188 complex of the peptide of claim 2.

21. A rhenium-186 or rhenium-188 complex of the peptide of claim 3.
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