Simple quantitative radioiodination of (E)-5-(2-iodovinyl)-2′-deoxyuridine (IVDU) by exchange labelling

Verbruggen, Alfons; Julien, Chris; Clercq, Erik De; Roo, M. De

doi:10.1016/0883-2889(86)90126-7

Cited by 7 publications

(2 citation statements)

References 17 publications

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“…Several strategies have been reported for the synthesis of radiolabeled IVDU. Radiohalogen exchange has been shown to be effective for the synthesis of lower specific activity product . Similarly, carrier-added and high specific activity products have been isolated in respectable radiochemical yields using modified Hunsdiecker reactions .…”

Section: Chemistrymentioning

confidence: 99%

“…Radiohalogen exchange has been shown to be effective for the synthesis of lower specific activity product. 20 Similarly, carrier-added and high specific activity products have been isolated in respectable radiochemical yields using modified Hunsdiecker reactions. 21 Recent reports for the highly efficient radiosyntheses of labeled IVAU from vinylstannane and vinylsilane precursors under mild conditions are particularly appealing.…”

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Cellular Uptake of 2‘-Substituted Analogues of (E)-5-(2-[¹²⁵I]Iodovinyl)-2‘-deoxyuridine in Tumor Cells Transduced with the Herpes Simplex Type-1 Thymidine Kinase Gene. Evaluation as Probes for Monitoring Gene Therapy

et al. 1997

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A useful synthetic methodology was developed to synthesize and radiolabel a series of (E)-5-(2-[125I]iodovinyl)uracil nucleoside substrates for herpes simplex virus type-1 thymidine kinase (HSV-1 TK). (E)-5-(2-[125I]Iodovinyl)-2'-deoxyuridine ([125I]IVDU, 10), (E)-5-(2-[125I]iodovinyl)-2'-fluoro-2'-deoxyuridine ([125I]IVFRU, 11), (E)-5-(2-[125I]iodovinyl)-2'-fluoro-2'-deoxyarabinouridine ([125I]IVFAU, 12), and (E)-5-(2-[125I]iodovinyl)arabinouridine ([125I]IVAU, 13) were synthesized in 63-83% radiochemical yield by reaction of the unprotected (E)-5-(2-(trimethylsilyl)vinyl) precursors (6-9) with [125I]ICl. Cellular uptake of these labeled compounds (10-13) was evaluated in vitro. All compounds showed minimal uptake in the KBALB cell line. However, increased uptake was observed for all compounds in KBALB-STK cells which are transduced with a replication incompetent Moloney murine leukemia virus vector encoding the HSV-1 TK gene. The results indicate that uptake of these compounds in KBALB-STK cells is variable and highly dependent on the nature of the sugar 2'-substituent. When a fluoro (12) or a hydroxy (13) substituent is present in the arabinofuranosyl (up) configuration at the 2'-position, there is diminished cellular uptake in KBALB-STK cells relative to hydrogen (10) or fluorine (11) in the ribofuranosyl (down) configuration at the 2'-position. Our results indicate that radiolabeled IVFRU (11) is most promising for further in vivo studies.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Synthesis and Cellular Uptake of 2‘-Substituted Analogues of (E)-5-(2-[¹²⁵I]Iodovinyl)-2‘-deoxyuridine in Tumor Cells Transduced with the Herpes Simplex Type-1 Thymidine Kinase Gene. Evaluation as Probes for Monitoring Gene Therapy

et al. 1997

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An efficient, high specific activity radioiodination of 5‐(1‐hydroxy/methoxy‐2‐iodoethyl)‐2′‐deoxyuridine by isotope exchange labelling in pivalic acid melt

Iwashina

Kumar

Knaus

et al. 1990

Labelled Comp Radiopharmac

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Radioiodinated 5-(l-hydroxy-2-iodoethyl)-2'-deoxyuridine (la) and 5 -( l-methoxy-2-iodoethyl)-2'-deoxyuridine (a) were prepared from the corresponding unlabelled nucleosides (1 and 2) by isotope exchange in a pivalic acid melt.Compound la was obtained in 71.3% to 26.3% radiochemical yield with a specific activity range of 77 to 2486 GBq/mmol, and was prepared in 70.3% radiochemical yield at a specific activity of 100.6 GBq/mmol. Low temperatures and the mild reaction conditions encountered in the pivalic acid melt method, which reduce the extent of nucleoside decomposition, were essential for successful exchange radi oi odi nati on.Even under optimal conditions (7OoC; 100 min), the order in which the reagents were mixed was critical to obtain high radiochemical yields and to minimize chemical decomposition of the nucleosides.

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Inhibition of terminal N- and O-glycosylation specific for herpesvirus-infected cells: Mechanism of an inhibitor of sugar nucleotide transport across Golgi membranes

Olofsson¹,

Milla²,

Hirschberg³

et al. 1988

Virology

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Simple quantitative radioiodination of (E)-5-(2-iodovinyl)-2′-deoxyuridine (IVDU) by exchange labelling

Cited by 7 publications

References 17 publications

Synthesis and Cellular Uptake of 2‘-Substituted Analogues of (E)-5-(2-[¹²⁵I]Iodovinyl)-2‘-deoxyuridine in Tumor Cells Transduced with the Herpes Simplex Type-1 Thymidine Kinase Gene. Evaluation as Probes for Monitoring Gene Therapy

Synthesis and Cellular Uptake of 2‘-Substituted Analogues of (E)-5-(2-[¹²⁵I]Iodovinyl)-2‘-deoxyuridine in Tumor Cells Transduced with the Herpes Simplex Type-1 Thymidine Kinase Gene. Evaluation as Probes for Monitoring Gene Therapy

An efficient, high specific activity radioiodination of 5‐(1‐hydroxy/methoxy‐2‐iodoethyl)‐2′‐deoxyuridine by isotope exchange labelling in pivalic acid melt

Inhibition of terminal N- and O-glycosylation specific for herpesvirus-infected cells: Mechanism of an inhibitor of sugar nucleotide transport across Golgi membranes

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Simple quantitative radioiodination of (E)-5-(2-iodovinyl)-2′-deoxyuridine (IVDU) by exchange labelling

Cited by 7 publications

References 17 publications

Synthesis and Cellular Uptake of 2‘-Substituted Analogues of (E)-5-(2-[125I]Iodovinyl)-2‘-deoxyuridine in Tumor Cells Transduced with the Herpes Simplex Type-1 Thymidine Kinase Gene. Evaluation as Probes for Monitoring Gene Therapy

Synthesis and Cellular Uptake of 2‘-Substituted Analogues of (E)-5-(2-[125I]Iodovinyl)-2‘-deoxyuridine in Tumor Cells Transduced with the Herpes Simplex Type-1 Thymidine Kinase Gene. Evaluation as Probes for Monitoring Gene Therapy

An efficient, high specific activity radioiodination of 5‐(1‐hydroxy/methoxy‐2‐iodoethyl)‐2′‐deoxyuridine by isotope exchange labelling in pivalic acid melt

Inhibition of terminal N- and O-glycosylation specific for herpesvirus-infected cells: Mechanism of an inhibitor of sugar nucleotide transport across Golgi membranes

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Product

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Synthesis and Cellular Uptake of 2‘-Substituted Analogues of (E)-5-(2-[¹²⁵I]Iodovinyl)-2‘-deoxyuridine in Tumor Cells Transduced with the Herpes Simplex Type-1 Thymidine Kinase Gene. Evaluation as Probes for Monitoring Gene Therapy

Synthesis and Cellular Uptake of 2‘-Substituted Analogues of (E)-5-(2-[¹²⁵I]Iodovinyl)-2‘-deoxyuridine in Tumor Cells Transduced with the Herpes Simplex Type-1 Thymidine Kinase Gene. Evaluation as Probes for Monitoring Gene Therapy