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No-carrier-added synthesis of a 4-methyl-substituted meta-iodobenzylguanidine analogue.

Publication ,  Journal Article
Vaidyanathan, G; Affleck, DJ; Zalutsky, MR
Published in: Appl Radiat Isot
March 2005

Radioiodinated meta-iodobenzylguanidine (MIBG) is used in the diagnosis and therapy of various neuroendocrine tumors. As a part of our efforts to develop an MIBG analogue with improved characteristics for these applications, a synthesis of 3-[131I]iodo-4-methylbenzylguanidine ([131I]MeIBG) was developed. Unlabeled MeIBG and the tin precursor, N, N'-(bis-tert-butyloxycarbonyl)-N-(4-methyl-3-trimethylstannylbenzyl) guanidine were synthesized in two steps from 3-iodo-4-methylbenzylalcohol. Radioiodinated MeIBG was synthesized at a no-carrier-added level by the iododestannylation of the tin precursor in about 85% radiochemical yield. The accumulation of [131I]MeIBG (38.9+/-3.0% of input counts) by human neuroblastoma SK-N-SH cells in vitro was 87% that of [125I]MIBG (44.5+/-3.0%) and a number of Uptake-1 inhibiting conditions reduced the uptake of both tracers in this cell line to a similar degree suggesting that introduction of a methyl substituent at the 4-position of MIBG did not adversely affect its biological characteristics.

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Published In

Appl Radiat Isot

DOI

ISSN

0969-8043

Publication Date

March 2005

Volume

62

Issue

3

Start / End Page

435 / 440

Location

England

Related Subject Headings

  • Radiopharmaceuticals
  • Radionuclide Imaging
  • Nuclear Medicine & Medical Imaging
  • Neuroblastoma
  • Isotope Labeling
  • Iodine Radioisotopes
  • Humans
  • Cell Line, Tumor
  • 3211 Oncology and carcinogenesis
  • 3202 Clinical sciences
 

Citation

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Vaidyanathan, G., Affleck, D. J., & Zalutsky, M. R. (2005). No-carrier-added synthesis of a 4-methyl-substituted meta-iodobenzylguanidine analogue. Appl Radiat Isot, 62(3), 435–440. https://doi.org/10.1016/j.apradiso.2004.07.001
Vaidyanathan, G., D. J. Affleck, and M. R. Zalutsky. “No-carrier-added synthesis of a 4-methyl-substituted meta-iodobenzylguanidine analogue.Appl Radiat Isot 62, no. 3 (March 2005): 435–40. https://doi.org/10.1016/j.apradiso.2004.07.001.
Vaidyanathan G, Affleck DJ, Zalutsky MR. No-carrier-added synthesis of a 4-methyl-substituted meta-iodobenzylguanidine analogue. Appl Radiat Isot. 2005 Mar;62(3):435–40.
Vaidyanathan, G., et al. “No-carrier-added synthesis of a 4-methyl-substituted meta-iodobenzylguanidine analogue.Appl Radiat Isot, vol. 62, no. 3, Mar. 2005, pp. 435–40. Pubmed, doi:10.1016/j.apradiso.2004.07.001.
Vaidyanathan G, Affleck DJ, Zalutsky MR. No-carrier-added synthesis of a 4-methyl-substituted meta-iodobenzylguanidine analogue. Appl Radiat Isot. 2005 Mar;62(3):435–440.
Journal cover image

Published In

Appl Radiat Isot

DOI

ISSN

0969-8043

Publication Date

March 2005

Volume

62

Issue

3

Start / End Page

435 / 440

Location

England

Related Subject Headings

  • Radiopharmaceuticals
  • Radionuclide Imaging
  • Nuclear Medicine & Medical Imaging
  • Neuroblastoma
  • Isotope Labeling
  • Iodine Radioisotopes
  • Humans
  • Cell Line, Tumor
  • 3211 Oncology and carcinogenesis
  • 3202 Clinical sciences