Novel Carboranes with a DNA Binding Unit for the Treatment of Cancer by Boron Neutron Capture Therapy
- 7 March 2002
- journal article
- Published by Wiley in ChemBioChem
- Vol. 3 (2-3) , 219-225
- https://doi.org/10.1002/1439-7633(20020301)3:2/3<219::aid-cbic219>3.0.co;2-#
Abstract
The synthesis and biological evaluation of two ortho-carborane derivatives which contain a 5,6,7-trimethoxyindole (TMI) unit for use in boron neutron capture therapy is described. The TMI moiety is known to be the DNA-binding part of the highly potent anticancer agent duocarmycin A. The ortho-carborane derivatives were prepared from amino alkynes which were bound to a protected TMI carboxylic acid. Addition of decaborane(14) to the alkyne triple bond with subsequent removal of the tert-butoxycarbonyl (Boc) and benzyl protecting groups gave the desired product. Boron uptake from the ortho-carborane derivatives into B-16 melanoma cells was higher and faster than that observed with L-p-boronophenylalanine (BPA), which is in use in the clinic.Keywords
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