PMID: 11906271Mar 22, 2002Paper

Synthesis of the first diethylenetriaminepentahydroxamic acid (DTPH) bifunctional chelating agent

Bioconjugate Chemistry
Ahmad SafavyDonald J Buchsbaum

Abstract

Synthesis of a new pentahydroxamic acid bifunctional chelating agent (BCA), constructed on the aminoazaalkyl core of diethylenetriaminepentaacetic acid (DTPA), is reported. Rational modifications in the structure of DTPA, which could result in an enhancement of its chelation properties, add to the collection of diagnostic and therapeutic metals bound by this chelator, and might implement significant improvements in the in vivo behavior of this compound, are described. Further improvements in the stability of the ligand-metal complexes of DTPA may improve both diagnostic and therapeutic outcomes such as tumor-to-normal tissue ratios and target-delivered radioactivity. A combination of hydroxamate functions with the azaalkyl backbone of DTPA might be a suitable approach to generate such higher stabilities. This rationale may be justified by the well-known affinity of hydroxamates against different transition metals and favorable properties of DTPA as a versatile chelator. Thus, the N(4),N(alpha),N(alpha),N(epsilon),N(epsilon)-pentakis[[((N-hydroxy-N-methyl]carbonyl)methyl]-2, 6-diamino-4-azahexanoic hydrazide (5, DTPH) was designed and synthesized through a convergent synthesis and in 40.7% overall yield. Conjugation of this comp...Continue Reading

References

Feb 7, 1992·Journal of Medicinal Chemistry·T MimuraJ Matsumoto
Dec 2, 1999·Journal of Medicinal Chemistry·B BarlaamR Maciewicz
Mar 15, 2000·Journal of Clinical Oncology : Official Journal of the American Society of Clinical Oncology·M RadererI Virgolini
Jul 6, 2000·Journal of Medicinal Chemistry·C ApfelJ L Specklin

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Citations

Feb 20, 2007·Nuclear Medicine and Biology·Alexander T YordanovMichael R Zalutsky

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