Synthesis and in Vitro Evaluation of 5-closo- and 5-nido-Orthocarboranyluridines as Boron Carriers

Sugar-part modified closo-carboranyluridines, 5-(o-carboran-1-yl)-2′,3′-dideoxy-3′-thiauridine 5 and 5-(o-carboran-1-yl)-2′,3′-dideoxy-2′α-phenylthiouridine 6, were synthesized. These newly synthesized closo-carboranyluridines, 5 and 6, and previously synthesized 5-(o-carboran-1-yl)uridine 1 were co...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 70; no. 12; pp. 3103 - 3110
Main Authors Imamura, Ken-ichiro, Yamamoto, Yoshinori
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.12.1997
Chemical Soc Japan
Chemical Society of Japan
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Summary:Sugar-part modified closo-carboranyluridines, 5-(o-carboran-1-yl)-2′,3′-dideoxy-3′-thiauridine 5 and 5-(o-carboran-1-yl)-2′,3′-dideoxy-2′α-phenylthiouridine 6, were synthesized. These newly synthesized closo-carboranyluridines, 5 and 6, and previously synthesized 5-(o-carboran-1-yl)uridine 1 were converted to the corresponding nido-carboranyluridines 18, 19, and 17, respectively. Water-solubility of nido-type 17 was about 100 times higher than that of its closo-counterpart 1. Water-solubilities of sugar modified nido-types 18 and 19 were about 1000 times higher than those of their closo-counterparts 5 and 6 . Cytotoxicities of the nido-types (17 and 19) were about 10 times lower than those of the corresponding closo-counterparts (1 and 6, respectively). Cellular uptake of the nido-types (17 and 19) was in the level similar to that of the closo-counterparts (1 and 6, respectively), although it is often believed that cellular uptake of hydrophilic carboranes (nido-forms) is much lower than that of lipophilic closo-carboranes.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.70.3103