5-iodo-2-deoxyuridine

Prusoff WH, Chen MS, Fischer PH, Lin TS, Shiau GT, Schinazi RF, Walker J (1979) Antiviral iodinated pyrimidine deoxyribonucleosides 5-iodo-2 -deoxyuridine 5-iodo-2 -deoxycytidine 5-iodo-5 -amino-2, 5 -dideoxyuridine, Pharmacol Ther 7 1-34... 

Harrington KJ, et al. Targeted radiosensitisation by pegylated liposome-encapsulated 3, 5 -0-dipalmitoyl 5-iodo-2 -deoxyuridine in a head and neck cancer xenograft model. Br J Cancer 2004 91 366. 

Thiazolylzinc halides have been employed as nucleophiles in Negishi couplings [12-14]. 2-Thiazolylzinc chloride was prepared by deprotonation of thiazole followed by treatment with ZnCl2. Subsequent Negishi coupling of thiazolylzinc chloride with 5-iodo-2 -deoxyuridine 8 elaborated the 5-substituted pyrimidine nucleoside 9 with the assistance of one equivalent of ZnCl2 [14]. 

Most bacterial infections can be treated successfully with antibiotics, but the development of satisfactory antiviral agents has been slow. Yet we are susceptible to many dangerous virus diseases, and viruses also take a huge toll among domestic animals and plants.3 The first antiviral drug, 5-iodo-2 -deoxyuridine (idoxuridine), was introduced in 1962 and was used for 20 years by ophthalmologists to treat serious eye infections by the herpes simplex virus (HSV). 

E. A. L. Biessen, D. M. Beuting, H. Vietsch, M. K. Bijsterbosch, and T. J. C. Van Berkel, Specific targeting of the antiviral drug 5-Iodo 2 -deoxyuridine to the parenchymal liver cell using lactosylated poly-L-lysine,. /. Hepatol. 27 806-815 (1994). 

The 5-chloro, 5-bromo and 5-iodo derivatives of uracil are base analogues of thymine and, in cellular systems, can replace the latter in DNA u >. Furthermore, 5-iodo-2 -deoxyuridine is an antiherpes agent currently used for treatment of ocular herpes keratitis. By contrast, 5-fluorouracil can replace uracil in RNA, and, together with 5-fluoro-2 -deoxyuridine, is employed in tumour chemotherapy. All the foregoing are also known mutagens, and 5-bromouracil and its deoxyriboside are widely employed in studies on mutagenesis U9). 

Gangerosa, L. R, Park, N.-H., and Hill, J. M. lontophoretic assistance of 5-iodo-2 -deoxyuridine penetration into neonatal mice skin and effect of DNA synthesis. Proc. Soc. Exp. Biol. Med. 754 439, 1977. 

SYNS ALLERGAN 211 DENDRID l-(2-DEOXY-P-d-RIBOFURANOSYL)-5-IODOURACIL l-P-d-2 -DEOXYRIBOFURANOSYL-5-IODOURACIL EMANIL HERPESIL HERPIDU HERPLEX HERPLEX LIQUIFILM IDEXUR IDOXENE IDOXURIDIN IDOXURIDINE IDU IDUCHER IDULEA IDUOCULOS IDUR IDURIDIN 5-IODODE-OXYURIDINE 5-IODO-2 -DEOXYURIDINE 5-lODOURACIL DEOXYRIBOSIDE lUDR 5-IUDR JODDEOXIURIDIN KERECID NSC-39661 OPHTHALMADINE SKStF 14287 STOXIL SYNMIOL... 

IODO-5-CHLOROXINE see CHR500 S-IODODEOXYURIDINE see DASOOO 5-IODO-2 -DEOXYURIDINE see DASOOO 4-IODO-3,5-DIMETHYI--N-(2-METHYLPHENYL)-lH-PYRAZOLE-l-ACETAMDE see IEI700 4-IODO-3,5-DIMETHYL-N-(4-METHYLPHENYL)-lH-PYRAZOLE-l-ACETAXnDE see IEI740... 

Fidler I. J. (1970). Metastasis quantitative analysis of distribution and fate of tumor emboli labeled with I-5-iodo-2 -deoxyuridine. J. Natl. Cancer Inst. 45, 773-782. 

In an attempt to exploit the mannose-6-phosphate receptor system to facilitate the uptake of nucleotides, nucleoside adducts of D-mannose-6-pyrophosphate have been prepared. P -(5-Iodo-2 -deoxyuridine)-5, P -D-... 

The third synthetic application is demonstrated by alkenylation of 5-iodouracil and 5-iodouridine [Eq.(15)]. These iodides were allowed to couple with alkenyl(difluoro)methylsilanes to afford 5-alkenyl-substituted uracils and uridines, respectively, which are potent antitumor or antiviral agents. It is noteworthy that unprotected 5-iodo-2-deoxyuridine could be converted into the corresponding cross-... 

Gronowitz and co-workers have coupled 2-tributylstannylpyridine (and three other stannyl heterocycles) with hetaryl bromides in medium yields the presence of silver oxide was found to be necessaiy to facilitate these reactions [101]. Gutierrez et al. [102] have coupled various hetaryltins with 5-iodo-2 -deoxyuridine in medium to good yields. 

A new method for the synthesis oligonucleotides containing of 5-formyl-2 -deoxyuridine has been described. The protected phosphoramidite of 5-(l,2-dihydroxyethyl)-2 -deoxyuridine (181) was prepared from 5-iodo-2 -deoxyuridine in seven steps. Following deprotection of the oligomer, subsequent oxidation of the diol with sodium periodate yielded the formyl function which could also be reduced with sodium borohydride to yield the 5-hydroxymethyl compound. An... 

The H-phosphonate derivative of a tricyclic carbazole-like 2 -deoxycytidine (183) analogue has been synthesised via a Stille biaryl coupling on 5-iodo-2 -deoxyuridine followed by cyclisation. The carbazole nucleoside was incorporated in oligonucleotides and shown to pair specifically with guanine. Duplexes resulting from the carbazole analogue and complementary RNA have elevated... 

Two novel phosphoramidite derivatives of 2 -deoxynucleosides incorporating a pyranose-modified nucleic base have been synthesised and incorporated into short DNA sequences. The galactose-modified deoxyuridine phosphoramidite (52) was synthesised via a Heck reaction between 3, 5 -0,0-bis(tcrt-butyl-dimethylsilyl)-5-iodo-2 -deoxyuridine and 2,3,4,6-tetraacetyl-l-(6-hex-1-ynyl) galacto-pyranoside. Subsequent deprotection, 5 -0-tritylation and treatment with 2-0-cyanoethyl-iV,N-diisopropyl chlorophosphine in the presence of DIPEA offered (52) which was used for solid-phase synthesis of a new type of oligo DNA-galactose conjugate." ... 

Note 5-IdUr, resistance to 5-iodo-2-deoxyuridine 6-TGr, resistance to 6-thioguanine F3Tr, resistance to trifluorothymidine CA, chromosomal aberrations B, breaks UDS, unscheduled DNA synthesis SSB, single-strand breaks CAT-Tox clones detect alterations in DNA sequence or helical structure. 

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