The 5-hydroxyl of myo-inositol is essential for uptake into HSDM1C1 mouse fibrosarcoma cells.
We attempted to replace the myo-inositol in cellular inositol phosphatides with 5-deoxy-myo-inositol to evaluate the role of inositol 1,4,5-trisphosphate as a second messenger. This analog, lacking a 5-hydroxyl, might be incorporated into 5-deoxyphosphatidylinositol and converted to the corresponding phosphatidylcyclitol 4-phosphate but could not be converted to phosphatidylinositol 4,5-diphosphate, the precursor of the second messenger molecule inositol 1,4,5-trisphosphate. We synthesized 5-deoxy-myo-inositol and found that this analog does not replace myo-inositol as an essential growth factor for essential fatty acid deficient HSDM1C1 mouse fibrosarcoma cells. Furthermore, [5-3H]-5-deoxy-myo-inositol was neither incorporated into the phospholipids nor accumulated in the cytoplasm of these cells. It appears that this cell line has a specific myo-inositol uptake system that excludes a potentially harmful analog of inositol.
D000818:Animals; D001692:Biological Transport; D002455:Cell Division / Q000187:drug effects; D002460:Cell Line; D005354:Fibrosarcoma / Q000378:metabolism* / Q000473:pathology; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism* / Q000494:pharmacology; D007700:Kinetics; D051379:Mice; D010743:Phospholipids / Q000096:biosynthesis; D013329:Structure-Activity Relationship; D014316:Tritium
D010743:Phospholipids; D014316:Tritium; D007294:Inositol; C046273:5-deoxyinositol