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Volumn 28, Issue 1, 2009, Pages 56-66

Facile synthesis and anti-tumor cell activity of Se-containing nucleosides

Author keywords

Anticancer activity; Methylseleno functionality; Selenium chemoprevention; Selenium modified nucleoside

Indexed keywords

2' METHYLSELENO 2' DEOXYURIDINE; 3' METHYLSELENO 3' DEOXYTHYMIDINE; 5' METHYLSELENO 5' DEOXYTHYMIDINE; ANTINEOPLASTIC AGENT; NUCLEOSIDE DERIVATIVE; SELENIUM; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

EID: 58149159370     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770802581765     Document Type: Article
Times cited : (17)

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