Carborane Derivatives for Nuclide Therapy and Imaging: Synthesis and Radio-labelling

This thesis describes synthesis and radiohalogenation of closo-carborane and nido-carborate derivatives for application in nuclide therapy and imaging. The work could be divided in to four sections.In the first section, the synthesis of three boronated DNA-intercalators – 1–(N-9-acridinyl-3-aminopropyl)-para-carborane-12-carboxylic acid hydrogen chloride, 1-[1-(N-9-acridinyl-3-aminopropyl)-para-carborane 12-(3-propyloxi)]-1,3-propanediol, 1-(N-9-acridinyl-3-amino-propyl)-1-ortho-carborane-2-ylmethoxy)1-3-propandiol – for potential use in BNCT, using targeted delivery is described.The second section describes the application of the Heck-reaction to 2-iodo-para-carborane, which has successfully been reacted with a number of styrene derivatives, i.e. para-phenyl, chloro, bromo, nitro, methoxy, and methyl-styrene…


1. Introduction
1.1. Chemistry of boranes and carboranes
1.1.1. General background
1.1.2. Chemical transformations of carboranes
1.2. Nuclide therapy and diagnostics
1.2.1. General background
1.2.2. Radio halogens
1.3. Targeting
1.3.1. Liposomes and drug loading
1.3.2. The two-step targeting
1.4. Boron Neutron Capture Therapy
1.4.1. Clinical trial
1.4.2. Some physical aspects of BNCT
1.4.3. Boronated compounds
2. Boron-containing DNA-intercalators (I and VI)
2.1. DNA intercalators
2.1.1. Acridines
2.2. Synthesis of some novel carborane-containing acridines
2.3.1. Synthesis of the Boronated Acridine Acid, BAA
2.3.2. Synthesis of the Boronated Acridine Diols, BAD I and II
3. TheHeckreactionappliedtocarboranechemistry
3.1. The Heck reaction
3.2. Palladium-catalysed Heck coupling of 2-iodo-para-carborane (II)
4. Radio-labelling of carborane compound
4.1. Radio-iodination of closo-carboranes using palladium catalysed isotopic exchange reactions (III)
4.2. Radio-bromination of closo-carboranes using palladium catalysed halogen
exchange reactions (IV)
4.3. Radio-bromination of the nido-carborate derivative Na+[nido-7-(para-C6H4NCS)-7,8-C2B9H11]-, NBI (V)

Author: Winberg, Karl Johan

Source: Uppsala University Library

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