Title:
METHOD FOR THE LINKAGE OF BIFUNCTIONAL CHELATING AGENTS AND (RADIOACTIVE) TRANSITION METAL COMPLEXES TO PROTEINS AND PEPTIDES
Document Type and Number:
WIPO Patent Application WO2004106939
Kind Code:
A3
Abstract:
The present invention relates to a method for radioactive labeling of a protein or peptide, by providing a protein or peptide having at least one glutamine or lysine residue; adding a metal chelating agent having at least one lysine or glutamine residue, respectively, which metal chelating agent is optionally complexed with a radioactive or paramagnetic metal; reacting the protein or peptide and metal chelating agent in the presence of a transglutaminase to obtain a protein or peptide with a metal chelating group covalently bound thereto, and optionally complexing the metal chelating group with a radioactive or paramagnetic metal. The invention also relates to proteins and peptides thus labeled and to proteins and peptides that have been coupled to a metal chelating agent but not yet labeled.
More Like This:
Inventors:
SCHIBLI ROGER (CH)
STICHELBERGER ALBERT (CH)
WAIBEL ROBERT (CH)
SCHUBIGER AUGUST (CH)
STICHELBERGER ALBERT (CH)
WAIBEL ROBERT (CH)
SCHUBIGER AUGUST (CH)
Application Number:
PCT/EP2004/005964
Publication Date:
March 17, 2005
Filing Date:
June 02, 2004
Export Citation:
Assignee:
SCHERRER INST PAUL (CH)
SCHIBLI ROGER (CH)
STICHELBERGER ALBERT (CH)
WAIBEL ROBERT (CH)
SCHUBIGER AUGUST (CH)
SCHIBLI ROGER (CH)
STICHELBERGER ALBERT (CH)
WAIBEL ROBERT (CH)
SCHUBIGER AUGUST (CH)
International Classes:
C07D213/38; C07F13/00; G01N33/534; (IPC1-7): G01N33/60; G01N33/532; C07D213/38; C07F13/00
Domestic Patent References:
| WO1992010761A1 | 1992-06-25 |
Other References:
LI LIN ET AL: "Reduction of kidney uptake in radiometal labeled peptide linkers conjugated to recombinant antibody fragments. Site-specific conjugation of DOTA-peptides to a Cys-diabody", BIOCONJUGATE CHEMISTRY, vol. 13, no. 5, September 2002 (2002-09-01), pages 985 - 995, XP002305956, ISSN: 1043-1802
BAIDOO KWAMENA E ET AL: "Design, synthesis, and initial evaluation of high-affinity technetium bombesin analogues", BIOCONJUGATE CHEMISTRY, vol. 9, no. 2, March 1998 (1998-03-01), pages 218 - 225, XP002306027, ISSN: 1043-1802
WILHELM B ET AL: "Transglutaminases: purification and activity assays", 20 July 1996, JOURNAL OF CHROMATOGRAPHY B : BIOMEDICAL APPLICATIONS, ELSEVIER SCIENCE PUBLISHERS, NL, PAGE(S) 163-177, ISSN: 0378-4347, XP004044279
GRIFFIN MARTIN ET AL: "Transglutaminases: Nature's biological glues.", BIOCHEMICAL JOURNAL, vol. 368, no. 2, 1 December 2002 (2002-12-01), pages 377 - 396, XP002305957, ISSN: 0264-6021
JOLLEY C ET AL: "Improved Synthesis and Characterisation of a Hydrazide Derivative of Diethylenetriaminepentaacetic Acid for Site-specific Labelling of Monoclonal Antibodies with <111>In", APPLIED RADIATION AND ISOTOPES, PERGAMON PRESS LTD., EXETER, GB, vol. 47, no. 7, 1 July 1996 (1996-07-01), pages 623 - 626, XP004050535, ISSN: 0969-8043
FOLK J E ET AL: "POLY AMINES AS PHYSIOLOGICAL SUBSTRATES FOR TRANS GLUTAMINASES", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 255, no. 8, 1980, pages 3695 - 3700, XP002305958, ISSN: 0021-9258
WAIBEL R ET AL: "Novel site-specific enzymatic radiolabeling of proteins and peptides with the 99m-Tc-tricarbonyl complex using transglutaminase.", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 46, no. Supplement 1, August 2003 (2003-08-01), & 15TH INTERNATIONAL SYMPOSIUM ON RADIOPHARMACEUTICAL CHEMISTRY; SYDNEY, AUSTRALIA; AUGUST 10-14, 2003, pages S23, XP002305959, ISSN: 0362-4803
BREEMAN WOUT A P ET AL: "Evaluation of radiolabelled bombesin analogues for receptor-targeted scintigraphy and radiotherapy", INTERNATIONAL JOURNAL OF CANCER, vol. 81, no. 4, 17 May 1999 (1999-05-17), pages 658 - 665, XP002306028, ISSN: 0020-7136
BAIDOO KWAMENA E ET AL: "Design, synthesis, and initial evaluation of high-affinity technetium bombesin analogues", BIOCONJUGATE CHEMISTRY, vol. 9, no. 2, March 1998 (1998-03-01), pages 218 - 225, XP002306027, ISSN: 1043-1802
WILHELM B ET AL: "Transglutaminases: purification and activity assays", 20 July 1996, JOURNAL OF CHROMATOGRAPHY B : BIOMEDICAL APPLICATIONS, ELSEVIER SCIENCE PUBLISHERS, NL, PAGE(S) 163-177, ISSN: 0378-4347, XP004044279
GRIFFIN MARTIN ET AL: "Transglutaminases: Nature's biological glues.", BIOCHEMICAL JOURNAL, vol. 368, no. 2, 1 December 2002 (2002-12-01), pages 377 - 396, XP002305957, ISSN: 0264-6021
JOLLEY C ET AL: "Improved Synthesis and Characterisation of a Hydrazide Derivative of Diethylenetriaminepentaacetic Acid for Site-specific Labelling of Monoclonal Antibodies with <111>In", APPLIED RADIATION AND ISOTOPES, PERGAMON PRESS LTD., EXETER, GB, vol. 47, no. 7, 1 July 1996 (1996-07-01), pages 623 - 626, XP004050535, ISSN: 0969-8043
FOLK J E ET AL: "POLY AMINES AS PHYSIOLOGICAL SUBSTRATES FOR TRANS GLUTAMINASES", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 255, no. 8, 1980, pages 3695 - 3700, XP002305958, ISSN: 0021-9258
WAIBEL R ET AL: "Novel site-specific enzymatic radiolabeling of proteins and peptides with the 99m-Tc-tricarbonyl complex using transglutaminase.", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 46, no. Supplement 1, August 2003 (2003-08-01), & 15TH INTERNATIONAL SYMPOSIUM ON RADIOPHARMACEUTICAL CHEMISTRY; SYDNEY, AUSTRALIA; AUGUST 10-14, 2003, pages S23, XP002305959, ISSN: 0362-4803
BREEMAN WOUT A P ET AL: "Evaluation of radiolabelled bombesin analogues for receptor-targeted scintigraphy and radiotherapy", INTERNATIONAL JOURNAL OF CANCER, vol. 81, no. 4, 17 May 1999 (1999-05-17), pages 658 - 665, XP002306028, ISSN: 0020-7136
Download PDF: