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Carborane Derivatives for Nuclide Therapy and Imaging: Synthesis and Radio-labelling
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
2003 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

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, to furnish the desired trans-β-2-B-para-carborane)styrene.

In the third section, radio-iodination and radio-bromination of closo-carboranes is described. Reaction of the corresponding iodinated carborane, in the presence of palladium catalyst, [125I]iodinated and [76Br]brominated carboranes were obtained in high to excellent yields.

Section four describes a method for indirect radiolabelling of antibodies with 76Br. It was shown that NBI, a isothiocyanatobenzene derivative of dodecahydro-7,8-dicarba-nido-undecaborate anion, could be radio-brominated using oxidative conditions. The radio-brominated NBI was thereafter conjugated to anti-HER2 antibody for biological evaluation.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis , 2003. , p. 52
Series
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1104-232X ; 881
Keywords [en]
Organic chemistry
Keywords [sv]
Organisk kemi
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-3561ISBN: 91-554-5722-3 (print)OAI: oai:DiVA.org:uu-3561DiVA, id: diva2:163258
Public defence
2003-10-02, B22, BMC, Uppsala, 10:15 (English)
Opponent
Supervisors
Available from: 2003-09-09 Created: 2003-09-09 Last updated: 2009-11-23Bibliographically approved
List of papers
1. Synthesis of boronated acridine carboxylic acid as a possible agent for BNCT.
Open this publication in new window or tab >>Synthesis of boronated acridine carboxylic acid as a possible agent for BNCT.
Manuscript (Other academic)
Identifiers
urn:nbn:se:uu:diva-90779 (URN)
Available from: 2003-09-09 Created: 2003-09-09 Last updated: 2010-01-13Bibliographically approved
2. Palladium-catalysed Heck reactions of styrene derivatives and 2-I-p-carborane
Open this publication in new window or tab >>Palladium-catalysed Heck reactions of styrene derivatives and 2-I-p-carborane
2003 In: Journal of Organic Chemistry, Vol. 68, no 9, p. 3569-3573Article in journal (Refereed) Published
Identifiers
urn:nbn:se:uu:diva-90780 (URN)
Available from: 2003-09-09 Created: 2003-09-09Bibliographically approved
3. High yield [125I]-labelling of iodinated carboranes by palladium-catalysed isotopic exchange
Open this publication in new window or tab >>High yield [125I]-labelling of iodinated carboranes by palladium-catalysed isotopic exchange
Show others...
2003 In: Journal of Organometallic Chemistry, Vol. 680, p. 182-192Article in journal (Refereed) Published
Identifiers
urn:nbn:se:uu:diva-90781 (URN)
Available from: 2003-09-09 Created: 2003-09-09 Last updated: 2014-03-05Bibliographically approved
4. Radiobromination of closo-carboranes using palladium-catalyzed halogen exchange
Open this publication in new window or tab >>Radiobromination of closo-carboranes using palladium-catalyzed halogen exchange
2005 (English)In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 48, no 3, p. 195-202Article in journal (Refereed) Published
Keywords
halogen exchange, carboranes, [76Br]bromide, labelling, palladium, catalyst
National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-69999 (URN)10.1002/jlcr.914 (DOI)
Available from: 2005-04-13 Created: 2005-04-13 Last updated: 2017-11-21Bibliographically approved
5. Radio-bromination of anti-HER2/neu/erbB-2 monoclonal antibody using p-isothiocyanatobenzene derivative of the [76Br]undecahydro-bromo-7,8-dicarba-nido-undecaborate(1-).
Open this publication in new window or tab >>Radio-bromination of anti-HER2/neu/erbB-2 monoclonal antibody using p-isothiocyanatobenzene derivative of the [76Br]undecahydro-bromo-7,8-dicarba-nido-undecaborate(1-).
In: Article in journal (Refereed) Submitted
Identifiers
urn:nbn:se:uu:diva-90783 (URN)
Available from: 2003-09-09 Created: 2003-09-09 Last updated: 2014-03-05Bibliographically approved
6. Synthesis of some novel boronated acridine compounds for possible use in BNCT.
Open this publication in new window or tab >>Synthesis of some novel boronated acridine compounds for possible use in BNCT.
Show others...
Manuscript (Other academic)
Identifiers
urn:nbn:se:uu:diva-90784 (URN)
Available from: 2003-09-09 Created: 2003-09-09 Last updated: 2010-01-13Bibliographically approved

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