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The Radiopharmaceutical Chemistry of the Radioisotopes of Copper

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Abstract

There are five radioisotopes of copper that are suitable for use in nuclear imaging or targeted radionuclide therapy: copper-67, copper-64, copper-62, copper-61, and copper-60. The diverse nuclear properties of these radionuclides include half-lives ranging from 10 min to 62 h and decay pathways via positron (β+) and beta-minus (β−) emission. Single-photon emission computed tomography (SPECT) as well as radionuclide therapy can be performed using copper-67, while the quartet of other radioisotopes decays via positron emission for positron emission tomography (PET). Two current foci of research into the radiopharmaceutical chemistry of copper are the creation of new coordination architectures for the radiometal and the development of relatively simple radiolabeling techniques that will lead to agents that remain stable in vivo. This chapter will discuss the production of the various radionuclides, the development of chelators for copper(II), and the applications of copper radiopharmaceuticals in both imaging and therapy.

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Abbreviations

AD:

Alzheimer’s disease

ALS:

Amyotrophic lateral sclerosis

AmBaSar:

4-((8-Amino-3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosan-1-yl)amino)benzoic acid

ATSM:

Diacetyl-bis(N 4-methylthiosemicarbazone)

Aβ:

Amyloid-β

BLIP:

Brookhaven Linac Isotope Producer

BNL:

Brookhaven National Laboratory

BTS:

Bis(thiosemicarbazone)

c(RGDfD):

cyclo(Arg-Gly-Asp-d-Phe-Asp)

c(RGDyK):

cyclo(Arg-Gly-Asp-d-Tyr-Lys)

CB-TE1A1P:

1,4,8,11-Tetraazabicyclo[6.6.2]hexadecane-4-acetic acid-11-methylphosphonic acid

CB-TE2A:

1,4,8,11-Tetraazabicyclo[6.6.2]hexadecane-4,11-diacetic acid

CT:

Computed tomography

DiamSar:

1,8-Diamino-3,6,10,13,16,19- hexaazabicyclo[6,6,6]-eicosane

DOTA:

1,4,7,10-Tetraazacyclododecane-1,4-7,10-tetraacetic acid

E 0 :

Standard reduction potentials

EDTA:

Ethylenediaminetetraacetic acid

ETS:

Ethylglyoxal bis(thiosemicarbazone)

FAZA:

1-(5-Fluoro-5-deoxy-α-D- arabinofuranosyl)-2-nitroimidazole

FMISO:

Fluoromisonidazole

FRIB:

Facility for Rare Isotope Beams

GTS:

Glyoxal-bis(thiosemicarbazone)

GTSM:

Glyoxal-bis(N 4-methylthiosemicarbazone)

h:

Hours

keV:

Kilo-electron volts (103)

LANL:

Los Alamos National Lab

mAb:

Monoclonal antibody

MeCOSar:

5-(8-methyl-3,6,10,13,16,19-hexaaza-bicyclo[6.6.6]icosan-1-ylamino)-5-oxopentanoic acid

MeV:

Mega-electron volts (106)

MicroPET:

Miniaturized positron emission tomography

min:

Minutes

MSU:

Michigan State University

NODAGA:

1-(1,3-Carboxypropyl)-4,7- dicarboxymethyl-1,4,7-triazacyclononane

NOTA:

1,4,7-Tricarboxymethyl-1,4,7- triazacyclononane

NSCL:

National Superconducting Cyclotron Laboratory

PCBA:

1-[(1,4,7,10,13-Pentaazacyclopentaadec-1-yl)methyl]benzoic acid

PCB-TE2A:

1,4,8,11-Tetraazabicyclo[6.6.3]heptadecane-4,11-diacetic acid

PEG:

Polyethylene glycol

PET:

Positron emission tomography

pH:

Potential of hydrogen

PTSM:

Pyruvaldehyde-bis(N 4- methylthiosemicarbazone)

Sar/Sarcophagine:

3,6,10,13,16,19-Hexaazabicyclo(6,6,6)eicosane

SarAr:

N 1-(4-aminophenyl)-3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane-1,8-diamine

SOD1:

Superoxide dismutase 1

SPECT:

Single-photon emission computed tomography

SSR:

Somatostatin receptor

TATE:

Octreotate

TE2A(1,4-):

1,4,8,11-Tetraazacyclotetradecane-1,4-biacetic acid

TE2A(1,8-):

1,4,8,11-Tetraazacyclotetradecane-1,8-biacetic acid

TETA:

1,4,8,11-Tetraazacyclotetradecane-1,4,8,11-tetraacetic acid

Y3-TATE:

Tyrosine-3-octreotate

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Authors and Affiliations

  1. Department of Medicine, University of Pittsburgh, Pittsburgh, PA, USA

    Xiaoxi Ling & Carolyn J. Anderson

  2. Medical Isotope Research & Production (MIRP) Program, Collider Accelerator Department, Brookhaven National Laboratory, Upton, NY, USA

    Cathy S. Cutler

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  1. Xiaoxi Ling
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  2. Cathy S. Cutler
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  3. Carolyn J. Anderson
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Correspondence to Carolyn J. Anderson .

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  1. Department of Radiology, Memorial Sloan Kettering Cancer Center, New York, NY, USA

    Jason S. Lewis

  2. Department of Radiology and Nuclear Medicine, VU University Medical Center, Amsterdam, The Netherlands

    Albert D. Windhorst

  3. Department of Chemistry, Hunter College, City University of New York, New York, NY, USA

    Brian M. Zeglis

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Ling, X., Cutler, C.S., Anderson, C.J. (2019). The Radiopharmaceutical Chemistry of the Radioisotopes of Copper. In: Lewis, J., Windhorst, A., Zeglis, B. (eds) Radiopharmaceutical Chemistry. Springer, Cham. https://doi.org/10.1007/978-3-319-98947-1_19

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