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An alternative and expedient synthesis of radioiodinated 4-iodophenylalanine.

Publication ,  Journal Article
Vaidyanathan, G; McDougald, D; Grasfeder, L; Zalutsky, MR; Chin, B
Published in: Appl Radiat Isot
October 2011

Radiolabeled amino acids have been used extensively in oncology both as diagnostic and therapeutic agents. In our pursuit to develop radiopharmaceuticals to target breast cancer, we were interested in determining the uptake of radioiodinated 4-iodophenylalanine, among other labeled amino acids, in breast cancer cells. In this work, we have developed an alternative method for the synthesis of this agent. The novel tin precursor, (S)-tert-butyl 2-(tert-butoxycarbonylamino)-3-(4-(tributylstannyl)phenyl)propanoate (3) was synthesized from the known, corresponding iodo derivative. Initially, the labeled 4-iodophenylalanine was synthesized from the above tin precursor in two steps with radiochemical yields of 91.6 ± 2.7% and 83.7 ± 1.7% (n=5), for the radioiodination (first) and deprotection (second) step, respectively. Subsequently, it was synthesized in a single step with an average radiochemical yield of 94.8 ± 3.4% (n=5). After incubation with MCF-7 breast cancer cells for 60 min, an uptake of up to 49.0 ± 0.7% of the input dose was seen; in comparison, the uptake of [¹⁴C]phenylalanine under the same conditions was 55.9 ± 0.5%. Furthermore, the uptake of both tracers was inhibited to a similar degree in a concentration-dependent manner by both unlabeled phenylalanine and 4-iodophenylalanine. With [¹⁴C]phenylalanine as the tracer, IC₅₀ values of 1.45 and 2.50 mM were obtained for Phe and I-Phe, respectively, and these values for [¹²⁵I]I-Phe inhibition were 1.3 and 1.0 mM. In conclusion, an improved and convenient method for the synthesis of no-carrier-added 4-[(⁎)I]phenylalanine was developed and the radiotracer prepared by this route demonstrated an amino acid transporter-mediated uptake in MCF-7 breast cancer cells in vitro that was comparable to that of [¹⁴C]phenylalanine.

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Published In

Appl Radiat Isot

DOI

EISSN

1872-9800

Publication Date

October 2011

Volume

69

Issue

10

Start / End Page

1401 / 1406

Location

England

Related Subject Headings

  • Radiopharmaceuticals
  • Phenylalanine
  • Nuclear Medicine & Medical Imaging
  • Isotope Labeling
  • Iodine Radioisotopes
  • Humans
  • Female
  • Cell Line, Tumor
  • Carbon Radioisotopes
  • Breast Neoplasms
 

Citation

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MLA
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Vaidyanathan, G., McDougald, D., Grasfeder, L., Zalutsky, M. R., & Chin, B. (2011). An alternative and expedient synthesis of radioiodinated 4-iodophenylalanine. Appl Radiat Isot, 69(10), 1401–1406. https://doi.org/10.1016/j.apradiso.2011.05.004
Vaidyanathan, Ganesan, Darryl McDougald, Linda Grasfeder, Michael R. Zalutsky, and Bennett Chin. “An alternative and expedient synthesis of radioiodinated 4-iodophenylalanine.Appl Radiat Isot 69, no. 10 (October 2011): 1401–6. https://doi.org/10.1016/j.apradiso.2011.05.004.
Vaidyanathan G, McDougald D, Grasfeder L, Zalutsky MR, Chin B. An alternative and expedient synthesis of radioiodinated 4-iodophenylalanine. Appl Radiat Isot. 2011 Oct;69(10):1401–6.
Vaidyanathan, Ganesan, et al. “An alternative and expedient synthesis of radioiodinated 4-iodophenylalanine.Appl Radiat Isot, vol. 69, no. 10, Oct. 2011, pp. 1401–06. Pubmed, doi:10.1016/j.apradiso.2011.05.004.
Vaidyanathan G, McDougald D, Grasfeder L, Zalutsky MR, Chin B. An alternative and expedient synthesis of radioiodinated 4-iodophenylalanine. Appl Radiat Isot. 2011 Oct;69(10):1401–1406.
Journal cover image

Published In

Appl Radiat Isot

DOI

EISSN

1872-9800

Publication Date

October 2011

Volume

69

Issue

10

Start / End Page

1401 / 1406

Location

England

Related Subject Headings

  • Radiopharmaceuticals
  • Phenylalanine
  • Nuclear Medicine & Medical Imaging
  • Isotope Labeling
  • Iodine Radioisotopes
  • Humans
  • Female
  • Cell Line, Tumor
  • Carbon Radioisotopes
  • Breast Neoplasms