Cholesterol-Undecanoate-Glucose Conjugate

Cholesterol-undecanoate-glucose conjugate is a glucose-based lipid conjugate that has been used in the generation of brain-targeted liposomes. It forms a stable, ordered bilayer with phospholipids with the glucose moiety facing outward for the purpose of being recognized by glucose transporter 1 (GLUT1) on the blood-brain barrier. Intravenous and intranasal administration of fluorescently labeled liposomes containing cholesterol-undecanoate-glucose conjugate and encapsulating the antimalarial artesunate (Cay-11817) and the methylated pyrazine ligustrazine (Cay-29658) induces increased brain fluorescence intensity and a reduced infection rate in a mouse model of P. falciparum-induced cerebral malaria when compared with fluorescently labeled non-cholesterol-undecanoate-glucose conjugate-containing liposomes encapsulating artesunate and ligustrazine.Formal Name: (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 11-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenoxy)undecanoate. Molecular Formula: C50H80O9. Formula Weight: 825.2. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml, Ethanol: 2 mg/ml. lambdamax: 225, 285 nm. SMILES: C[C@]12CC[C@H](OC(CCCCCCCCCCOC3=CC=C(O[C@H](O[C@@H]4CO)[C@H](O)[C@@H](O)[C@@H]4O)C=C3)=O)CC1=CC[C@]5([H])[C@]2([H])CC[C@@]6(C)[C@@]5([H])CC[C@]6([H])[C@@H](CCCC(C)C)C. InChi Code: InChI=1S/C50H80O9/c1-33(2)15-14-16-34(3)40-24-25-41-39-23-18-35-31-38(26-28-49(35,4)42(39)27-29-50(40,41)5)57-44(52)17-12-10-8-6-7-9-11-13-30-56-36-19-21-37(22-20-36)58-48-47(55)46(54)45(53)43(32-51)59-48/h18-22,33-34,38-43,45-48,51,53-55H,6-17,23-32H2,1-5H3/t34-,38+,39+,40-,41+,42+,43-,45-,46+,47-,48-,49+,50-/m1/s1. InChi Key: PUBVMZACKXEFKF-HZGKWGMYSA-N.