Amino acid analogs for tumor imaging

Goodman, Mark M; Shoup, Timothy

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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:

Goodman, Mark M ^[1]; Shoup, Timothy ^[2]

Atlanta, GA
Decatur, GA

Issue Date:: Tue Oct 06 00:00:00 EDT 1998

Research Org.:: Oak Ridge National Laboratory (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 C07B - GENERAL METHODS OF ORGANIC CHEMISTRY

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A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
A61K2123/00 - Preparations for testing in vivo
A61K51/0478 - {complexes from non-cyclic ligands, e.g. EDTA, MAG3}
A61K51/0487 - {Metallocenes, i.e. complexes based on a radioactive metal complexed by two cyclopentadienyl anions}

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07B - GENERAL METHODS OF ORGANIC CHEMISTRY
C07B59/001 - {Acyclic or carbocyclic compounds}

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C229/20 - the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
C07C229/30 - the carbon skeleton being acyclic and unsaturated
C07C229/48 - with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
C07C2601/04 - with a four-membered ring
C07C2601/08 - the ring being saturated
C07C2601/10 - the ring being unsaturated
C07C2601/14 - The ring being saturated
C07C2601/16 - the ring being unsaturated
C07C45/30 - with halogen containing compounds, e.g. hypohalogenation
C07C45/59 - in five-membered rings
C07C49/255 - containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
C07C49/753 - containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
C07F13/005 - {Compounds without a metal-carbon linkage}

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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.

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                    Goodman, Mark M, & Shoup, Timothy. Amino acid analogs for tumor imaging.  United States.

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                    Goodman, Mark M, and Shoup, Timothy. Tue .  
        "Amino acid analogs for tumor imaging".  United States.  https://www.osti.gov/servlets/purl/871880.

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@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         = {Tue Oct 06 00:00:00 EDT 1998},

  month        = {Tue Oct 06 00:00:00 EDT 1998}

}

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Works referenced in this record:

Radiopharmaceuticals II: Proceedings 2nd International Symposium on Radiopharmaceuticals, March 19–22, 1979, Seattle, Washington
journal, December 1980

Sheahan, Jim
American Journal of Health-System Pharmacy, Vol. 37, Issue 12
https://doi.org/10.1093/ajhp/37.12.1698a

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

Bey, Philippe; Vevert, Jean Paul; Van Dorsselaer, Viviane
The Journal of Organic Chemistry, Vol. 44, Issue 15
https://doi.org/10.1021/jo01329a029

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

Di Chiro, G.; DeLaPaz, R. L.; Brooks, R. A.
Neurology, Vol. 32, Issue 12
https://doi.org/10.1212/WNL.32.12.1323

New pilot laboratory freeze dryer
journal, January 1977

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Vacuum, Vol. 27, Issue 10-11, p. 621
https://doi.org/10.1016/S0042-207X(77)80453-3

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

Kuntschke, Dirk; Wenzel, Martin; Schulze, Paul
Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 36, Issue 2
https://doi.org/10.1002/jlcr.2580360212

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

Meegalla, Sanath K.; Plössl, Karl; Kung, Mei-Ping
Journal of Medicinal Chemistry, Vol. 40, Issue 1
https://doi.org/10.1021/jm960532j

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

Chiotellis, E.; Subramanian, G.; McAfee, J. G.
International Journal of Nuclear Medicine and Biology, Vol. 4, Issue 1
https://doi.org/10.1016/0047-0740(77)90039-0

Labeling Cyclic Glycoprotein IIb/IIIa Receptor Antagonists with ^99m Tc by the Preformed Chelate Approach: Effects of Chelators on Properties of [ ^99m Tc]Chelator−Peptide Conjugates
journal, January 1996

Liu, Shuang; Edwards, D. Scott; Looby, Richard J.
Bioconjugate Chemistry, Vol. 7, Issue 2
https://doi.org/10.1021/bc9500958

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Amino acid analogs for tumor imaging

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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 substantiallymore » « less
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Similar Records

Title: Amino acid analogs for tumor imaging

Abstract

Citation Formats

Radiopharmaceuticals II: Proceedings 2nd International Symposium on Radiopharmaceuticals, March 19–22, 1979, Seattle, Washington journal, December 1980

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 pilot laboratory freeze dryer journal, January 1977

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

Labeling Cyclic Glycoprotein IIb/IIIa Receptor Antagonists with 99m Tc by the Preformed Chelate Approach: Effects of Chelators on Properties of [ 99m Tc]Chelator−Peptide Conjugates journal, January 1996

Radiopharmaceuticals II: Proceedings 2nd International Symposium on Radiopharmaceuticals, March 19–22, 1979, Seattle, Washington
journal, December 1980

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 pilot laboratory freeze dryer
journal, January 1977

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

Labeling Cyclic Glycoprotein IIb/IIIa Receptor Antagonists with ^99m Tc by the Preformed Chelate Approach: Effects of Chelators on Properties of [ ^99m Tc]Chelator−Peptide Conjugates
journal, January 1996