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Meta-iodobenzylguanidine derivatives containing a second guanidine moiety.

Publication ,  Journal Article
Vaidyanathan, G; Shankar, S; Affleck, DJ; Alston, K; Norman, J; Welsh, P; LeGrand, H; Zalutsky, MR
Published in: Bioorg Med Chem
April 1, 2004

Radioiodinated meta-iodobenzylguanidine (MIBG) is used in the diagnosis and therapy of various neuroendocrine tumors. To investigate whether an additional guanidine function in the structure of MIBG will yield analogues that may potentially enhance tumor-to-target ratios, two derivatives-one with a guanidine moiety and another with a guanidinomethyl group at the 4-position of MIBG-were prepared. In the absence of any uptake-1 inhibiting conditions, the uptake of 4-guanidinomethyl-3-[(131)I]iodobenzylguanidine ([(131)I]GMIBG) by SK-N-SH cells in vitro was 1.7+/-0.1% of input counts, compared to a value of 40.3+/-1.4% for [(125)I[MIBG suggesting that guanidinomethyl group at the 4-position negated the biological properties of MIBG. On the other hand, 4-guanidino-3-[(131)I]iodobenzylguanidine ([(131)I]GIBG) had an uptake (5.6+/-0.3%) that was 12-13% that of [(125)I]MIBG (46.1+/-2.7%), and the ratio of uptake by control over DMI-treated (nonspecific) cultures was higher for [(131)I]GIBG (20.9+/-0.3) than [(125)I]MIBG itself (15.0+/-2.7). The exocytosis of [(131)I]GIBG and [(125)I]MIBG from SK-N-SH cells was similar. The uptake of [(131)I]GIBG in the mouse target tissues, heart and adrenals, as well as in a number of other tissues was about half that of [(125)I]MIBG. These results suggest that substitution of guanidine functions, especially a guanidinomethyl group, in MIBG structure may not be advantageous.

Duke Scholars

Published In

Bioorg Med Chem

DOI

ISSN

0968-0896

Publication Date

April 1, 2004

Volume

12

Issue

7

Start / End Page

1649 / 1656

Location

England

Related Subject Headings

  • Tissue Distribution
  • Molecular Structure
  • Mice
  • Medicinal & Biomolecular Chemistry
  • Iodine Radioisotopes
  • In Vitro Techniques
  • Humans
  • Guanidines
  • Drug Screening Assays, Antitumor
  • Cell Survival
 

Citation

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MLA
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Vaidyanathan, G., Shankar, S., Affleck, D. J., Alston, K., Norman, J., Welsh, P., … Zalutsky, M. R. (2004). Meta-iodobenzylguanidine derivatives containing a second guanidine moiety. Bioorg Med Chem, 12(7), 1649–1656. https://doi.org/10.1016/j.bmc.2004.01.026
Vaidyanathan, Ganesan, Sriram Shankar, Donna J. Affleck, Kevin Alston, Joseph Norman, Philip Welsh, Holly LeGrand, and Michael R. Zalutsky. “Meta-iodobenzylguanidine derivatives containing a second guanidine moiety.Bioorg Med Chem 12, no. 7 (April 1, 2004): 1649–56. https://doi.org/10.1016/j.bmc.2004.01.026.
Vaidyanathan G, Shankar S, Affleck DJ, Alston K, Norman J, Welsh P, et al. Meta-iodobenzylguanidine derivatives containing a second guanidine moiety. Bioorg Med Chem. 2004 Apr 1;12(7):1649–56.
Vaidyanathan, Ganesan, et al. “Meta-iodobenzylguanidine derivatives containing a second guanidine moiety.Bioorg Med Chem, vol. 12, no. 7, Apr. 2004, pp. 1649–56. Pubmed, doi:10.1016/j.bmc.2004.01.026.
Vaidyanathan G, Shankar S, Affleck DJ, Alston K, Norman J, Welsh P, LeGrand H, Zalutsky MR. Meta-iodobenzylguanidine derivatives containing a second guanidine moiety. Bioorg Med Chem. 2004 Apr 1;12(7):1649–1656.
Journal cover image

Published In

Bioorg Med Chem

DOI

ISSN

0968-0896

Publication Date

April 1, 2004

Volume

12

Issue

7

Start / End Page

1649 / 1656

Location

England

Related Subject Headings

  • Tissue Distribution
  • Molecular Structure
  • Mice
  • Medicinal & Biomolecular Chemistry
  • Iodine Radioisotopes
  • In Vitro Techniques
  • Humans
  • Guanidines
  • Drug Screening Assays, Antitumor
  • Cell Survival