Meta-iodobenzylguanidine derivatives containing a second guanidine moiety.

@article{Vaidyanathan2004MetaiodobenzylguanidineDC,
  title={Meta-iodobenzylguanidine derivatives containing a second guanidine moiety.},
  author={Ganesan Vaidyanathan and Sriram Shankar and Donna J. Affleck and Kevin L. Alston and Joseph Norman and Philip C. Welsh and Holly LeGrand and Michael R Zalutsky},
  journal={Bioorganic \& medicinal chemistry},
  year={2004},
  volume={12 7},
  pages={
          1649-56
        }
}
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… Expand
9 Citations
No-carrier-added synthesis of a 4-methyl-substituted meta-iodobenzylguanidine analogue.
  • G. Vaidyanathan, D. Affleck, M. Zalutsky
  • Chemistry, Medicine
  • Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine
  • 2005
TLDR
The accumulation of [131I]MeIBG by human neuroblastoma SK-N-SH cells in vitro was 87% that of [125I]MIBG, suggesting that introduction of a methyl substituent at the 4-position of MIBG did not adversely affect its biological characteristics. Expand
A 4-methyl-substituted meta-iodobenzylguanidine analogue with prolonged retention in human neuroblastoma cells
TLDR
Introduction of a methyl group at the 4-position of MIBG seems to be advantageous in terms of higher tumour retention in vitro and lower hepatic uptake in vivo, however, the slower blood clearance of MeIBG may be problematic for some applications. Expand
Synthesis and biological effects of new hybrid compounds composed of benzylguanidines and the alkylating group of busulfan on neuroblastoma cells.
TLDR
Uptake and toxicity of hybrids mBBG and pBBG in human neuroblastoma cells compared favorably to their ancestors [(131)I]-mIBG and busulfan. Expand
A tin precursor for the synthesis of no‐carrier‐added [*I]MIBG and [211At]MABG
Radioiodinated MIBG has shown considerable promise as an imaging agent for cardiac and oncologic applications, and also as a targeted radiotherapeutic for treating patients with neuroendocrineExpand
Design, synthesis, and biological evaluation of bifunctional thyrointegrin inhibitors: new anti-angiogenesis analogs
TLDR
The synthesis of compounds incorporating long-chain moieties guanidine, urea, methyl amine and, propyl amine substitutions into the core molecular framework of tetrac were undertaken and the evaluation of the anti-angiogenic bioactivity of these compounds in the CAM model revealed no loss of activity. Expand
Molecular Scaffolds as Double-Targeting Agents For the Diagnosis and Treatment of Neuroblastoma.
TLDR
A family of novel Y-shaped scaffolds has been synthesized, which have structural analogues of MIBG covalently attached at each end of the Y-structure, yielding one specific Y- shaped structure able to be engulfed by the malignant cells, and accumulates in the tumoral tissue, at significantly higher levels than the structure containing only one single targeting agent. Expand
A new targeting agent for the selective drug delivery of nanocarriers for treating neuroblastoma.
TLDR
Novel targeting agents against neuroblastoma based on the meta-iodobenzylguanidine (MIBG) moiety were synthesized and biologically evaluated for nanocarrier vectorization, resulting in the improved cellular uptake in tumoral cells. Expand
Heavy atom enhanced generation of singlet oxygen in novel indenofluorene-based two-photon absorbing chromophores for photodynamic therapy
Abstract A series of indenofluorene-based two-photon absorbing chromophores ( FL0 , FL-2BrN , FL-1IN , FL-2IN , and FL-2IS ) have been designed and synthesized for photodynamic therapy (PDT).Expand
A model of modified meta-iodobenzylguanidine conjugated gold nanoparticles for neuroblastoma treatment
127I-modified mIBG was successfully synthesized and grafted covalently to the surface of carboxylated PEG-GNPs. The particles were not toxic to the normal fibroblast cells while specificallyExpand

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