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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| Published in | Bulletin of the Chemical Society of Japan Vol. 70; no. 12; pp. 3103 - 3110 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
TOKYO
The Chemical Society of Japan
01.12.1997
Chemical Soc Japan Chemical Society of Japan |
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| Abstract | 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. |
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| AbstractList | 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. 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'alpha-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 nide-type 17 was about 100 times higher than that of its close-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 close-counterparts (1 and 6, respectively). Cellular uptake of the nido-types (17 and 19) was in the level similar to that of the close-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. Abstract 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. |
| Author | Imamura, Ken-ichiro Yamamoto, Yoshinori |
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| CitedBy_id | crossref_primary_10_1039_C8NJ00819A crossref_primary_10_1016_j_bmc_2004_07_032 crossref_primary_10_1021_jm020047q crossref_primary_10_1002_chin_199817235 crossref_primary_10_1021_om800319w crossref_primary_10_1021_jm0701977 crossref_primary_10_1016_j_drudis_2017_08_009 crossref_primary_10_1021_jm0491896 crossref_primary_10_1016_S0022_328X_99_00129_1 crossref_primary_10_1021_ic000768k crossref_primary_10_1021_ic101620h crossref_primary_10_1016_S0022_328X_00_00574_X |
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| Keywords | CANCER-CELLS ACID RELATED-COMPOUNDS P-BORONOPHENYLALANINE ANALOGS INVITRO NEUTRON-CAPTURE THERAPY BIOLOGICAL PROPERTIES STEREOCHEMISTRY GLYCOSYLATION NUCLEOSIDE BASES |
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| Snippet | 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,... Sugar-part modified closo-carboranyluridines, 5-(o-carboran-1-yl)-2',3'-dideoxy-3'-thiauridine 5 and... Abstract Sugar-part modified closo-carboranyluridines, 5-(o-carboran-1-yl)-2′,3′-dideoxy-3′-thiauridine 5 and... 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,... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | Synthesis and in Vitro Evaluation of 5-closo- and 5-nido-Orthocarboranyluridines as Boron Carriers |
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