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Synthesis of 18F- and 76Br-labelled oligonucleotide and nucleoside derivatives
Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
1998 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

With the aim of developing synthetic routes to oligodeoxynucleotides and analogues labelled with the positron-emitting radionuclides 18F and 76Br (half-lives 1.8 and 16.2 h, respectively), a number of compounds containing amine-reactive electrophiles were synthesised and used in preparation of oligodeoxynucleotide derivatives labelled in the 5´-position. Some 76Br-labelled nucleoside derivatives, which might be useful in the preparation of oligodeoxynucleotides containing a 5-[76Br]bromouracil unit, were also synthesised.

The novel compounds 4-([18F]fluoromethyl)phenyl isothiocyanate and N-succinimidyl 4-[76Br]bromobenzoate were prepared in 13-15% and 45-60% isolated radiochemical yields, respectively. The previously reported N-succinimidyl [18F]fluorobenzoate was prepared by a modified procedure. The reactions of these compounds with oligodeoxynucleotides and phosphorothioate oligodeoxynucleotides (6- to 30-mers) modified in the 5´-position with a hexylamine group were investigated. With regard to chemical stability, an aromatic position of the halogen was found superior in the conditions of the oligodeoxynucleotide labelling reaction. Using the 18F- and 76Br-labelled succinimidyl esters, labelled oligodeoxynucleotidesand phosphorothioate oligodeoxynucleotides were obtained in 5-19% isolated radiochemical yield.

The 76Br-labelled nucleoside 5-[76Br]bromo-2´-deoxyuridine was prepared in 60% isolated radiochemical yield. The corresponding phosphoramidite derivative 5´-O-[bis(4-methoxyphenyl)-phenylmethyI]-5-[76Br]bromo-2´-deoxyuridine 3´-[(2-cyanoethyl)-bis(1-methylethyl)phosphoramidite], was synthesised in 19-24% radio-chemical yield.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis , 1998. , 38 p.
Series
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1104-232X ; 364
Keyword [en]
Chemistry
Keyword [sv]
Kemi
National Category
Chemical Sciences
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-876ISBN: 91-554-4203-X (print)OAI: oai:DiVA.org:uu-876DiVA: diva2:172083
Public defence
1998-04-29, the Svedberg Lecture Hall, Institute of Chemistry, Uppsala University, Uppsala, 10:15
Available from: 1998-04-08 Created: 1998-04-08Bibliographically approved

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