Synthesis and antitumor activity of new alkyl glycoglycerolipids

Морозова, Н. Г.; Timofeev, Grigoriy A.; Timakova, A.A.; Shmendel, Elena V.; Kubasova, T. S.; Tyutyunnik, Lubava L.; Markova, Alina A.; Маслов, М. А.; Shtil, Alexander A.

doi:10.1016/j.mencom.2015.07.003

Cited by 6 publications

(2 citation statements)

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“… Synthesis of lactose ether lipid 70.3 and its analogue 70.6 featuring a carbamate function as linker [ 224 ]. …”

Section: Reviewmentioning

confidence: 99%

“…This gain of function was applied to vasorelaxation assays [223]. In 2015, the group of N. G. Morozova reported in a communication the synthesis of analogues of ohmline in which the methoxy group in position 2 of glycerol was replaced by an ethoxy group and other derivatives with a carbamate linker between the glycerol and the saccharide unit [224]. The synthesis started from the diether 70.1 that was glycosylated with a bromide glycosyl donor like hepta-acetylated lactose 70.2 in the presence of mercury salts (Figure 70).…”

Section: Saccharide Unit On Position 3 Of Glycerolmentioning

confidence: 99%

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Synthesis of ether lipids: natural compounds and analogues

Gomes,

Bauduin,

Le Roux

et al. 2023

Beilstein J. Org. Chem.

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Ether lipids are compounds present in many living organisms including humans that feature an ether bond linkage at the sn-1 position of the glycerol. This class of lipids features singular structural roles and biological functions. Alkyl ether lipids and alkenyl ether lipids (also identified as plasmalogens) correspond to the two sub-classes of naturally occurring ether lipids. In 1979 the discovery of the structure of the platelet-activating factor (PAF) that belongs to the alkyl ether class of lipids increased the interest in these bioactive lipids and further promoted the synthesis of non-natural ether lipids that was initiated in the late 60’s with the development of edelfosine (an anticancer drug). More recently, ohmline, a glyco glycero ether lipid that modulates selectively SK3 ion channels and reduces in vivo the occurrence of bone metastases, and other glyco glycero ether also identified as GAEL (glycosylated antitumor ether lipids) that exhibit promising anticancer properties renew the interest in this class of compounds. Indeed, ether lipid represent a new and promising class of compounds featuring the capacity to modulate selectively the activity of some membrane proteins or, for other compounds, feature antiproliferative properties via an original mechanism of action. The increasing interest in studying ether lipids for fundamental and applied researches invited to review the methodologies developed to prepare ether lipids. In this review we focus on the synthetic method used for the preparation of alkyl ether lipids either naturally occurring ether lipids (e.g., PAF) or synthetic derivatives that were developed to study their biological properties. The synthesis of neutral or charged ether lipids are reported with the aim to assemble in this review the most frequently used methodologies to prepare this specific class of compounds.

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“… Synthesis of lactose ether lipid 70.3 and its analogue 70.6 featuring a carbamate function as linker [ 224 ]. …”

Section: Reviewmentioning

confidence: 99%

Section: Saccharide Unit On Position 3 Of Glycerolmentioning

confidence: 99%