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Synthesis and evaluation of thymidine kinase 1-targeting carboranyl pyrimidine nucleoside analogs for boron neutron capture therapy of cancer.

Abstract：

:A library of sixteen 2nd generation amino- and amido-substituted carboranyl pyrimidine nucleoside analogs, designed as substrates and inhibitors of thymidine kinase 1 (TK1) for potential use in boron neutron capture therapy (BNCT) of cancer, was synthesized and evaluated in enzyme kinetic-, enzyme inhibition-, metabolomic-, and biodistribution studies. One of these 2nd generation carboranyl pyrimidine nucleoside analogs (YB18A [3]), having an amino group directly attached to a meta-carborane cage tethered via ethylene spacer to the 3-position of thymidine, was approximately 3-4 times superior as a substrate and inhibitor of hTK1 than N5-2OH (2), a 1st generation carboranyl pyrimidine nucleoside analog. Both 2 and 3 appeared to be 5'-monophosphorylated in TK1(+) RG2 cells, both in vitro and in vivo. Biodistribution studies in rats bearing intracerebral RG2 glioma resulted in selective tumor uptake of 3 with an intratumoral concentration that was approximately 4 times higher than that of 2. The obtained results significantly advance the understanding of the binding interactions between TK1 and carboranyl pyrimidine nucleoside analogs and will profoundly impact future design strategies for these agents.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Agarwal HK,Khalil A,Ishita K,Yang W,Nakkula RJ,Wu LC,Ali T,Tiwari R,Byun Y,Barth RF,Tjarks W

doi

10.1016/j.ejmech.2015.05.042

subject

Has Abstract

pub_date

2015-07-15 00:00:00

pages

197-209

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(15)30069-6

journal_volume

100

pub_type

杂志文章

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