Chemical and biochemical studies on carbohydrate esters. IX. Antitumor effects of selectively fatty acylated products of maltose.

Abstract

Selective fatty acylation of maltose was carried out by heating an equimolar mixture of the disaccharide and an appropriate acid chloride in pyridine. The resulting crude product was chromatographed to furnish two preparations, termed maltose-[mono]- and-[high]-esters ; the former preparation was an isomeric mixture of monoesters among which the 1-, 6-, and 6'-isomers were presumably predominant, and the latter consisted of di-, tri-, and poly-esters, as indicated by gas-liquid and thin-layer chromatographies. The antitumor effects of the maltose-[mono]-esters of stearic, palmitic, myristic, lauric, and caprylic acids towards Ehrlich ascites carcinoma in mice were tested by the total packed cell volume method, by intraperitoneal injection. The stearic, palmitic, and myristic esters proved to be effective, while the lauric and caprylic esters exhibited a slight effect and no effect, respectively. The antitumor effect of the maltose-[mono]-stearate upon the same tumor was compared with that of the analogous derivative of sucrose by survival bioassay (intraperitoneal administration) at various doses. Both compounds showed similar antitumor results, giving especially marked effects at the dose of 50 mg/kg/day×5. These two compounds also exerted moderate growth-inhibitory effects against solid sarcoma 180 in mice when they were administered subcutaneously ; in the case of sucrose-[mono]-stearate, intramuscular injection was also effective. The maltose-[high]-esters of stearic, palmitic, and myristic acids failed to exert marked activity upon this solid tumor by either administration route.