The syntheses and in vivo biodistribution of novel boronated unnatural amino acids

George Kabalka, Zhongzhi Wu, M. L. Yao, N. Natarajan

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A series of boronated, unnatural amino acids were prepared and their biodistribution determined in melanoma bearing mice. The unnatural amino acids were prepared utilizing recently developed borylation. The majority of the syntheses utilize metal catalyzed additions of diboron agents to unsaturated carbonyl compounds. Biodistribution studies in mice bearing melanoma tumors indicated that all the boronated amino acids were taken up by the melanoma tumors. The data for the cyclic five-membered ring analogue, 1-amino-3-boronocyclopentanecarboxylic acid, was most striking, exhibiting a nearly 22:1 ratio of boron concentration for tumor to brain at the 2h time point, dropping to 7.3 after 6h. The tumor to blood and tumor to skin ratios were also quite high. It is important to note that all of the amino acids were synthesized as racemic and diastereomeric mixtures. Thus there is a high probability that a single enantiomer of 1-amino-3-boronocyclopentanecarboxylic acid might exhibit far higher selectivity.

Original languageEnglish (US)
Pages (from-to)1111-1115
Number of pages5
JournalApplied Radiation and Isotopes
Volume61
Issue number5
DOIs
StatePublished - Nov 1 2004

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amino acids
tumors
synthesis
mice
acids
carbonyl compounds
enantiomers
blood
brain
boron
selectivity
analogs
rings
metals

All Science Journal Classification (ASJC) codes

  • Radiation

Cite this

The syntheses and in vivo biodistribution of novel boronated unnatural amino acids. / Kabalka, George; Wu, Zhongzhi; Yao, M. L.; Natarajan, N.

In: Applied Radiation and Isotopes, Vol. 61, No. 5, 01.11.2004, p. 1111-1115.

Research output: Contribution to journalArticle

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