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Details for Patent: 5,965,107

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Details for Patent: 5,965,107

Title: Technetium-99m labeled peptides for imaging
Abstract:This invention relates to radiolabeled peptides and methods for producing such peptides. Specifically, the invention relates to peptides, methods and kits for making such peptides, and methods for using such peptides to image sites in a mammalian body labeled with technetium-99m (Tc-99m) via a radiolabel-binding moiety which forms a neutral complex with Tc-99m.
Inventor(s): Dean; Richard T. (Bedford, NH), Buttram; Scott (Derry, NH), McBride; William (Manchester, NH), Lister-James; John (Bedford, NH), Civitello; Edgar R. (Londonderry, NH)
Assignee: Diatide, Inc. (Londonderry, NH)
Filing Date:Apr 20, 1992
Application Number:07/871,282
Claims:1. A complex formed by reacting technetium-99m and a reducing agent with a reagent comprising

a) a peptide that specifically binds to a target in vivo; and

b) a radiolabel binding moiety covalently linked to the peptide; wherein the complex between said technetium-99m and said moiety is electrically neutral, avoiding interference by the complex with specific binding of the peptide to the target.

2. The complex of claim 1, wherein the reducing agent is selected from the group consisting of a dithionite ion, a stannous ion, and a ferrous ion.

3. A complex formed by labeling a reagent comprising

a) a peptide that specifically binds to a target in vivo; and

b) a radiolabel binding moiety covalently linked to the peptide; with technetium-99m by ligand exchange of a prereduced technetium-99m complex, wherein the complex between said technetium-99m and said moiety is electrically neutral, avoiding interference by the complex with specific binding of the pettide to the target.

4. The complex of claims 1, 2, or 3, wherein the moiety has a formula selected from the group consisting of: ##STR8## wherein each R is independently H, CH.sub.3 or C.sub.2 H.sub.5 ; each (pgp).sup.s is independently a thiol protecting group or H;

m, n and p are independently 2 or 3;

A=linear or cyclic lower alkyl, aryl, heterocyclyl, a combination thereof;

X=a bond covalently linking the moiety to the peptide;

and ##STR9## wherein each R is independently H, CH.sub.3 or C.sub.2 H.sub.5 ; m, n and p are independently 2 or 3;

A=linear or cyclic lower alkyl, aryl, heterocyclyl, a combination thereof;

V=H or --CO-X;

R'=H or X;

X=a bond covalently linking the moiety to the peptide;

and wherein when V=H, R'=peptide and when R'=H, V=--CO-peptide.

5. The complex of claims 1, 2, or 3, wherein the peptide is selected from the group consisting of:

formyl-MLF;

(VGVAPG).sub.3 amide;

(VPGVG).sub.4 amide;

RALVDTLKFVTQAEGAKamide (SEQ ID NO: 1);

RALVDTEFKVKQEAGAKamide (SEO ID NO: 2):

PLARITLPDFRLPEIAIPamide (SEQ ID NO: 3);

GQQHHLGGAKAGDV (SEQ ID NO: 4);

PLYKKIIKKLLES (SEQ ID NO: 5);

LRALVDTLKamide (SEQ ID NO: 6);

GGGLRALVDTLKamide (SEQ ID NO: 7);

GGGLRALVDTLKFVTQAEGAKamide (SEQ ID NO: 8);

GGGRALVDTLKALVDTLamide (SEQ ID NO: 9);

GHRPLDKKREEAPSLRPAPPPISGGGYR (SEQ ID NO: 10);

PSPSPIHPAHHKRDRRQamide (SEQ ID NO: 11);

GGGF.sub.D.Cpa.YW.sub.D KTFTamide; ##STR10## {SYNRGDSTC(S-maleimido)CH.sub.2 CH.sub.2 -}.sub.3 N]GCGGGLRALVDTLKamide (SEQ ID NO: 13);

GCYRALVDTLKFVTQAEGAKamide (SEQ ID NO: 14); and

GC(VGVAPG).sub.3 amide.

6. A method for imaging a site within a mammalian body comprising the steps of administering an effective diagnostic amount of the complex of claims 1, 2 or 3, and detecting the technetium-99m localized at the site.

7. A method for imaging a site within a mammalian body comprising the steps of administering an effective diagnostic amount of the complex of claim 5, and detecting the technetium-99m localized at the site.

8. An electrically neutral complex formed between technetium-99m and a radiolabel-binding moiety covalently linked to a peptide having specific binding properties, wherein interference with said properties by said complex is avoided.
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