Selective antiproliferative activity of hydroxynaphthyl-beta-D-xylosides.
The antiproliferative activity of the 14 isomeric monoxylosylated dihydroxynaphthalenes has been tested in vitro toward normal HFL-1 and 3T3 A31 cells as well as transformed T24 and 3T3 SV40 cells. The antiproliferative effect toward HFL-1 cells was correlated with the polarity of the compounds. However, in the case of transformed T24 cells, some compounds showed a clearly different behavior resulting in a selective antiproliferative effect. No such correlation was found for normal 3T3 A31 or virus transformed 3T3 SV40 cells, nor for the free aglycon. These results suggest that the antiproliferative activity shown by naphthoxylosides is diverse in different cell lines and dependent on the nature of the aglycon. The antiproliferative effect of 2-(6-hydroxynaphthyl)-beta-D-xylopyranoside, in contrast to inactive 2-naphthyl-beta-D-xylopyranoside, on T24 cells was accompanied by increased apoptosis as indicated by a TUNEL assay.
Department of Organic Chemistry, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
Mårten
M
Jacobsson
Ulf
U
Ellervik
Mattias
M
Belting
Katrin
K
Mani
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D002240:Carbohydrate Sequence; D002460:Cell Line; D002461:Cell Line, Transformed; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D051379:Mice; D008969:Molecular Sequence Data; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D006027:Glycosides; D009284:Naphthols; C010807:xylosides