Synthesis of macrocyclic polyaminocarboxylates and their use for preparing stable radiometal antibody immunoconjugates for therapy, spect and pet imaging
Abstract
A simple method for the synthesis of 1,4,7,10-tetraazacyclododecane N,N'N",N'"-tetraacetic acid and 1,4,8,11-tetraazacyclotetradecane N,N',N",N'"-tetraacetic acid involves cyanomethylating 1,4,7,10-tetraazacyclododecane or 1,4,8,11-tetraazacyclotetradecane to form a tetranitrile and hydrolyzing the tetranitrile. These macrocyclic compounds are functionalized through one of the carboxylates and then conjugated to various biological molecules including monoclonal antibodies. The resulting conjugated molecules are labeled with radiometals for SPECT and PET imaging and for radiotherapy.
- Inventors:
-
- Fairfax, VA
- Stony Brook, NY
- Setauket, NY
- Issue Date:
- Research Org.:
- Associated Universities, Inc., Upton, NY (United States)
- OSTI Identifier:
- 869952
- Patent Number(s):
- 5428156
- Application Number:
- 08/042,249
- Assignee:
- Associated Universities, Inc. (Washington, DC)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
- DOE Contract Number:
- AC02-76CH00016
- Resource Type:
- Patent
- Country of Publication:
- United States
- Language:
- English
- Subject:
- synthesis; macrocyclic; polyaminocarboxylates; preparing; stable; radiometal; antibody; immunoconjugates; therapy; spect; pet; imaging; simple; method; 10-tetraazacyclododecane; -tetraacetic; acid; 11-tetraazacyclotetradecane; involves; cyanomethylating; form; tetranitrile; hydrolyzing; compounds; functionalized; carboxylates; conjugated; various; biological; molecules; including; monoclonal; antibodies; resulting; labeled; radiometals; radiotherapy; -tetraacetic acid; biological molecules; stable radiometal; radiometal antibody; acetic acid; monoclonal antibodies; pet imaging; various biological; macrocyclic compounds; molecules including; antibody immunoconjugates; simple method; macrocyclic polyaminocarboxylates; /999/
Citation Formats
Mease, Ronnie C, Mausner, Leonard F, and Srivastava, Suresh C. Synthesis of macrocyclic polyaminocarboxylates and their use for preparing stable radiometal antibody immunoconjugates for therapy, spect and pet imaging. United States: N. p., 1995.
Web.
Mease, Ronnie C, Mausner, Leonard F, & Srivastava, Suresh C. Synthesis of macrocyclic polyaminocarboxylates and their use for preparing stable radiometal antibody immunoconjugates for therapy, spect and pet imaging. United States.
Mease, Ronnie C, Mausner, Leonard F, and Srivastava, Suresh C. Tue .
"Synthesis of macrocyclic polyaminocarboxylates and their use for preparing stable radiometal antibody immunoconjugates for therapy, spect and pet imaging". United States. https://www.osti.gov/servlets/purl/869952.
@article{osti_869952,
title = {Synthesis of macrocyclic polyaminocarboxylates and their use for preparing stable radiometal antibody immunoconjugates for therapy, spect and pet imaging},
author = {Mease, Ronnie C and Mausner, Leonard F and Srivastava, Suresh C},
abstractNote = {A simple method for the synthesis of 1,4,7,10-tetraazacyclododecane N,N'N",N'"-tetraacetic acid and 1,4,8,11-tetraazacyclotetradecane N,N',N",N'"-tetraacetic acid involves cyanomethylating 1,4,7,10-tetraazacyclododecane or 1,4,8,11-tetraazacyclotetradecane to form a tetranitrile and hydrolyzing the tetranitrile. These macrocyclic compounds are functionalized through one of the carboxylates and then conjugated to various biological molecules including monoclonal antibodies. The resulting conjugated molecules are labeled with radiometals for SPECT and PET imaging and for radiotherapy.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Jun 27 00:00:00 EDT 1995},
month = {Tue Jun 27 00:00:00 EDT 1995}
}
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Works referenced in this record:
Investigations of N-linked macrocycles for 111in and 90Y labeling of proteins
journal, February 1992
- Wu, C.; Virzi, F.; Hnatowich, D. J.
- International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology, Vol. 19, Issue 2
Synthesis of nonionic gadolinium chelates useful as contrast agents for magnetic resonance imaging: 1,4,7-tris(carboxymethyl)-10-substituted-1,4,7,10-tetraazacyclododecanes and their corresponding gadolinium chelates
journal, March 1991
- Dischino, D. D.; Delaney, E. J.; Emswiler, J. E.
- Inorganic Chemistry, Vol. 30, Issue 6
The peptide way to macrocyclic bifunctional chelating agents: synthesis of 2-(p-nitrobenzyl)-1,4,7,10-tetraazacyclododecane-N,N',N",N'''-tetraacetic acid and study of its yttrium(III) complex
journal, August 1988
- Moi, Min K.; Meares, Claude F.; DeNardo, Sally J.
- Journal of the American Chemical Society, Vol. 110, Issue 18
Gd(DOTA): An alternative to Gd(DTPA) as aT1,2 relaxation agent for NMR imaging or spectroscopy
journal, October 1986
- Magerstädt, Michael; Gansow, Otto A.; Brechbiel, Martin W.
- Magnetic Resonance in Medicine, Vol. 3, Issue 5
Copper chelates as probes of biological systems: Stable copper complexes with a macrocyclic bifunctional chelating agent
journal, July 1985
- Moi, Min K.; Meares, Claude F.; McCall, Michael J.
- Analytical Biochemistry, Vol. 148, Issue 1
Synthesis of a kinetically stable yttrium-90 labelled macrocycle–antibody conjugate
journal, January 1989
- Cox, Jonathan P. L.; Jankowski, Karl J.; Kataky, Ritu
- J. Chem. Soc., Chem. Commun., Issue 12
Preparation and characterization of paramagnetic polychelates and their protein conjugates
journal, January 1990
- Sieving, Paul F.; Watson, Alan D.; Rocklage, Scott M.
- Bioconjugate Chemistry, Vol. 1, Issue 1
Nuclear magnetic resonance spectroscopy of lanthanide complexes with a tetraacetic tetraaza macrocycle. Unusual conformation properties
journal, May 1980
- Desreux, J. F.
- Inorganic Chemistry, Vol. 19, Issue 5
Simplified method for conjugating macrocyclic bifunctional chelating agents to antibodies via 2-iminothiolane
journal, May 1990
- McCall, Michael J.; Diril, Habibe; Meares, Claude F.
- Bioconjugate Chemistry, Vol. 1, Issue 3
Newer approaches to the radiolabeling of monoclonal antibodies by use of metal chelates
journal, January 1991
- Gansow, Otto A.
- International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology, Vol. 18, Issue 4
An efficient method for labelling antibodies with 111 In
journal, January 1984
- Buckley, R. G.; Searle, F.
- FEBS Letters, Vol. 166, Issue 1