title: An emulsion of sulfoquinovosylacylglycerol with long-chain alkanes increases its permeability to tumor cells.
abstract: The alpha-anomer form of sulfoquinovosyl-monoacylglycerol with a saturated C18 fatty acid (alpha-SQMG-C(18:0)) is a natural sulfolipid that is a clinically promising antitumor agent. It forms vesicles, micelles or an emulsion in water, depending on several physicochemical conditions. The type of aggregate formed appears to strongly influence the bioactivity level. Thus, we investigated the nature of the aggregates in relation to their bioactivities. The structure of the alpha-SQMG-C(18:0) assembly was greatly affected by the type of additive used in the preparation. Emulsification with ethanol and n-decane might be more effective at inhibiting tumor cell growth than the micelle or vesicle preparations. alpha-SQMG-C(18:0) formed an "emulsion-like-aggregate" in ethanol containing an n-decane concentration in the range of 1.03-103 mM: . These ethanol/n-alkane/alpha-SQMG-C(18:0) aggregates inhibited cell growth in a dose-dependent manner, under optimum conditions (i.e., ethanol containing 103 mM: of n-decane or n-dodecane dispersed in phosphate-buffered saline or culture medium). Based on these data, we discuss the relationship between the molecular action of and antitumor activity by alpha-SQMG-C(18:0).
authors.affiliation: Department of Applied of Biological Science, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba-ken 278-8510, Japan.
authors.forename: Satoko
authors.initials: S
authors.lastname: Aoki
authors.forename: Keisuke
authors.initials: K
authors.lastname: Ohta
authors.forename: Kenjiro
authors.initials: K
authors.lastname: Matsumoto
authors.forename: Hideki
authors.initials: H
authors.lastname: Sakai
authors.forename: Masahiko
authors.initials: M
authors.lastname: Abe
authors.forename: Masahiko
authors.initials: M
authors.lastname: Miura
authors.forename: Fumio
authors.initials: F
authors.lastname: Sugawara
authors.forename: Kengo
authors.initials: K
authors.lastname: Sakaguchi
mesh_terms: D000473:Alkanes / Q000008:administration & dosage; D000970:Antineoplastic Agents / Q000008:administration & dosage* / Q000737:chemistry / Q000493:pharmacokinetics*; D002455:Cell Division / Q000187:drug effects; D045744:Cell Line, Tumor; D004655:Emulsions; D000431:Ethanol / Q000008:administration & dosage; D006017:Glycolipids / Q000008:administration & dosage* / Q000737:chemistry / Q000493:pharmacokinetics*; D006367:HeLa Cells; D006801:Humans; D008823:Micelles; D010539:Permeability; D012997:Solvents
chemical_list: D000473:Alkanes; D000970:Antineoplastic Agents; D004655:Emulsions; D006017:Glycolipids; D008823:Micelles; D012997:Solvents; C496611:sulfoquinovosylacylglycerol; D000431:Ethanol; C012867:decane