Sulfoglycolipids analogues as new molecules for tumor treatment

The sulfoglycolipids sulfoquinovosylacylglycerols(SQAG) are abundant sulfur-containing glycerolipids that are associated with photosynthetic organisms especially with a large number of marine algae. Their main structural feature is the anionic head group constituent sulfoquinovose, a derivative of glucose in which the 6-hydroxyl is replaced by a sulfonate group, -linked to the sn-3 position of a diacylglycerol1. Recently reported biological activities of SQAGs, including inhibitory effects on HIV-reverse transcriptase, and mammalian DNA polymerase, proliferation of some cancer cell lines, angiogenesis (especially when coupled with tumor radiotherapy), and apoptosis induction, make these compounds very attractive for their potential in cancer therapy. Also, extractive SQAG mixtures are known to inhibit in vitro TPA induced tumor promotion stage. To obtain new active compounds for cancer therapy by structural modification of natural SQAGs, SQAG analogues have been synthesized in which the sulfoquinovose moiety is linked to the 2 position of glycerol carrying acyl chains of different length. Similar compounds in fact, with a 6’-hydroxyl instead of a 6’-sulfonate (namely some glycoglycerolipid analogues), are known to be active as anti-tumor-promoters in TPA promoted carcinogenesis in vitro and in vivo experiments. A synthetic strategy has been used to selectively insert the proper chemical functionalities (i.e. sulfonate and acyl chains) at the desired positions of the previously prepared glucosylglycerol skeleton to obtain the target compounds. Biological evaluation of anti-tumor activities will be performed including the study of their chemopreventing potential.