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Title: Amino acid analogs for tumor imaging

Abstract

The invention provides novel amino acid compounds of use in detecting and evaluating brain and body tumors. These compounds combine the advantageous properties of 1-amino-cycloalkyl-1-carboxylic acids, namely, their rapid uptake and prolonged retention in tumors with the properties of halogen substituents, including certain useful halogen isotopes including fluorine-18, iodine-123, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77 and bromine-82. In one aspect, the invention features amino acid compounds that have a high specificity for target sites when administered to a subject in vivo. Preferred amino acid compounds show a target to non-target ratio of at least 5:1, are stable in vivo and substantially localized to target within 1 hour after administration. An especially preferred amino acid compound is ›.sup.18 F!-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC). In another aspect, the invention features pharmaceutical compositions comprised of an .alpha.-amino acid moiety attached to either a four, five, or a six member carbon-chain ring. In addition, the invention features analogs of .alpha.-aminoisobutyric acid.

Inventors:
 [1];  [2]
  1. Atlanta, GA
  2. Decatur, GA
Issue Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
OSTI Identifier:
871880
Patent Number(s):
5817776
Application Number:
09/744444
Assignee:
Emory University (Atlanta, GA)
Patent Classifications (CPCs):
A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
DOE Contract Number:  
FG05-93ER61737
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
amino; acid; analogs; tumor; imaging; provides; novel; compounds; detecting; evaluating; brain; tumors; combine; advantageous; properties; 1-amino-cycloalkyl-1-carboxylic; acids; namely; rapid; uptake; prolonged; retention; halogen; substituents; including; useful; isotopes; fluorine-18; iodine-123; iodine-125; iodine-131; bromine-75; bromine-76; bromine-77; bromine-82; aspect; features; specificity; target; sites; administered; subject; vivo; preferred; non-target; ratio; stable; substantially; localized; hour; administration; especially; compound; 18; -1-amino-3-fluorocyclobutane-1-carboxylic; facbc; pharmaceutical; compositions; comprised; alpha; -amino; moiety; attached; five; six; carbon-chain; addition; -aminoisobutyric; compositions comprised; pharmaceutical compositions; compositions comprise; especially preferred; amino acid; carboxylic acids; carboxylic acid; provides novel; acid moiety; acid compounds; acid compound; acid analogs; prolonged retention; pharmaceutical composition; advantageous properties; tumor imaging; target site; halogen substituents; novel amino; compounds combine; halogen isotopes; evaluating brain; -amino acid; /999/

Citation Formats

Goodman, Mark M, and Shoup, Timothy. Amino acid analogs for tumor imaging. United States: N. p., 1998. Web.
Goodman, Mark M, & Shoup, Timothy. Amino acid analogs for tumor imaging. United States.
Goodman, Mark M, and Shoup, Timothy. Tue . "Amino acid analogs for tumor imaging". United States. https://www.osti.gov/servlets/purl/871880.
@article{osti_871880,
title = {Amino acid analogs for tumor imaging},
author = {Goodman, Mark M and Shoup, Timothy},
abstractNote = {The invention provides novel amino acid compounds of use in detecting and evaluating brain and body tumors. These compounds combine the advantageous properties of 1-amino-cycloalkyl-1-carboxylic acids, namely, their rapid uptake and prolonged retention in tumors with the properties of halogen substituents, including certain useful halogen isotopes including fluorine-18, iodine-123, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77 and bromine-82. In one aspect, the invention features amino acid compounds that have a high specificity for target sites when administered to a subject in vivo. Preferred amino acid compounds show a target to non-target ratio of at least 5:1, are stable in vivo and substantially localized to target within 1 hour after administration. An especially preferred amino acid compound is ›.sup.18 F!-1-amino-3-fluorocyclobutane-1-carboxylic acid (FACBC). In another aspect, the invention features pharmaceutical compositions comprised of an .alpha.-amino acid moiety attached to either a four, five, or a six member carbon-chain ring. In addition, the invention features analogs of .alpha.-aminoisobutyric acid.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1998},
month = {10}
}

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Works referenced in this record:

Direct synthesis of .alpha.-halogenomethyl-.alpha.-amino acids from the parent .alpha.-amino acids
journal, July 1979


Glucose utilization of cerebral gliomas measured by [18F] fluorodeoxyglucose and positron emission tomography
journal, December 1982


New [99mTc]-cytectrene amine compounds as specific brain imaging agents
journal, February 1995


Synthesis and Characterization of Technetium-99m-Labeled Tropanes as Dopamine Transporter-Imaging Agents
journal, January 1997


Preparation of Tc-99m labeled pyridoxal-amino acid complexes and their evaluation
journal, January 1977