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Meeting ReportRadiopharmaceutical Chemistry: New Radiopharmaceuticals

cis-1-[4-(Hydroxymethyl)-2-cyclopenten-1-yl]-5-iodovinyluracil as a new imaging agent for HSV-TK reporter gene

Eun Jung Kim, Tae Hyun Choi, Gwang Il An, Byung Soo Kim, Soon Hyuk Ahn, Cheol Moon, Byeong Il Kim, Gi Jeong Cheon, Chang Woon Choi and Sang Moo Lim
Journal of Nuclear Medicine May 2009, 50 (supplement 2) 1949;
Eun Jung Kim
1Korea Institute of Radiological and Medical Sciences, Department of Molecular Imaging Center, Seoul, South Korea
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Tae Hyun Choi
1Korea Institute of Radiological and Medical Sciences, Department of Molecular Imaging Center, Seoul, South Korea
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Gwang Il An
1Korea Institute of Radiological and Medical Sciences, Department of Molecular Imaging Center, Seoul, South Korea
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Byung Soo Kim
1Korea Institute of Radiological and Medical Sciences, Department of Molecular Imaging Center, Seoul, South Korea
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Soon Hyuk Ahn
1Korea Institute of Radiological and Medical Sciences, Department of Molecular Imaging Center, Seoul, South Korea
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Cheol Moon
1Korea Institute of Radiological and Medical Sciences, Department of Molecular Imaging Center, Seoul, South Korea
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Byeong Il Kim
1Korea Institute of Radiological and Medical Sciences, Department of Molecular Imaging Center, Seoul, South Korea
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Gi Jeong Cheon
1Korea Institute of Radiological and Medical Sciences, Department of Molecular Imaging Center, Seoul, South Korea
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Chang Woon Choi
1Korea Institute of Radiological and Medical Sciences, Department of Molecular Imaging Center, Seoul, South Korea
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Sang Moo Lim
1Korea Institute of Radiological and Medical Sciences, Department of Molecular Imaging Center, Seoul, South Korea
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Abstract

1949

Objectives While IVDU is an effective substrate for HSV-TK, it is not suitable for in vivo study because of C-N glycocidic bond cleavage by thymidine phosphorylase. A carbocyclic IVDU analogue, ddIVDU, is synthesized and possesses greater metabolic stability due to replacement of the furanose oxygen with carbon.

Methods A carbocyclic iodonucleoside analogue, cis-1-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-5-iodovinyluracil (ddIVDU) was synthesized from cyclopentadiene and glyoxylic acid as starting materials in 10 steps. The synthetic route for precursor employed cyclopentadiene as a starting material and proceed in good yield through 9 steps which contain hetero Diels-Alder reaction and Pd(0)-catalyzed coupling reaction as key reactions. For cytotoxicity analysis, MCA and MCA-TK (HSV-TK positive) cells were treated with various concentration of IVDU, ddIVDU, and GCV. Cytotoxicity was measured by the MTS methods. For in vitro uptake study, MCA and MCA-TK cells were incubated with 1uCi of [125I]IVDU and [125I]ddIVDU. The accumulation of each agent was measured after various incubation times.

Results IVDU and GCV were more toxic than ddIVDU in MCA-TK cells. But, in MCA cells, ddIVDU was more toxic than IVDU. Cell uptake of [125I]IVDU was higher than [125I]ddIVDU in MCA-TK cell. And also, higher accumulation of [125I]ddIVDU was observed more in the acid-insoluble fraction than the acid-soluble fraction of MCA-TK cell lysates. By contrast with [125I]ddIVDU, [125I]IVDU showed high accumulation in the acid-soluble fraction.

Conclusions These results revealed that metabolic stability of ddIVDU was improved than IVDU.

  • © 2009 by Society of Nuclear Medicine
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Journal of Nuclear Medicine
Vol. 50, Issue supplement 2
May 2009
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cis-1-[4-(Hydroxymethyl)-2-cyclopenten-1-yl]-5-iodovinyluracil as a new imaging agent for HSV-TK reporter gene
Eun Jung Kim, Tae Hyun Choi, Gwang Il An, Byung Soo Kim, Soon Hyuk Ahn, Cheol Moon, Byeong Il Kim, Gi Jeong Cheon, Chang Woon Choi, Sang Moo Lim
Journal of Nuclear Medicine May 2009, 50 (supplement 2) 1949;

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cis-1-[4-(Hydroxymethyl)-2-cyclopenten-1-yl]-5-iodovinyluracil as a new imaging agent for HSV-TK reporter gene
Eun Jung Kim, Tae Hyun Choi, Gwang Il An, Byung Soo Kim, Soon Hyuk Ahn, Cheol Moon, Byeong Il Kim, Gi Jeong Cheon, Chang Woon Choi, Sang Moo Lim
Journal of Nuclear Medicine May 2009, 50 (supplement 2) 1949;
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