Interaction of cholesterol with synthetic sphingomyelin derivatives in mixed monolayers
| Autor: | Slotte Jp, Lotte Gronberg, Ruan Zs, Bittman R |
|---|---|
| Rok vydání: | 1991 |
| Předmět: |
1
2-Dipalmitoylphosphatidylcholine Chemical Phenomena Molecular Structure Cholesterol oxidase Chemistry Physical Cholesterol Oxidase Stereochemistry Chemistry Cholesterol technology industry and agriculture Phospholipid Biochemistry Chemical synthesis Sphingomyelins Structure-Activity Relationship chemistry.chemical_compound Membrane Liposomes Monolayer Alkoxy group lipids (amino acids peptides and proteins) Sphingomyelin |
| Zdroj: | Biochemistry. 30:10746-10754 |
| ISSN: | 1520-4995 0006-2960 |
| DOI: | 10.1021/bi00108a020 |
| Popis: | To study the structural requirements of the molecular interactions between cholesterol and sphingomyelins in model membranes, sphingomyelin derivatives were synthesized in which (a) the 3-hydroxy group was replaced with a hydrogen atom or with a methoxy, ethoxy, or tetrahydropyranyloxy group, (b) the N-acyl chain length was varied, and (c) the N-acyl chain length contained an alpha-hydroxy group. The chemical syntheses of these derivatives from DL-erythro-sphingosine are reported. The properties of these sphingomyelin derivatives were examined in monolayer membranes at the air/water interface. The mean molecular area of the pure N-stearoylsphingomyelin derivatives was determined, and the effects of cholesterol on the condensation of sphingomyelin packing in the monolayer were recorded. It was observed that replacement of the 3-hydroxy group of sphingomyelin with a hydrogen atom or its substitution with a methoxy or ethoxy group did not affect the ability of cholesterol to condense the molecular packing in monolayers. Even when a bulky tetrahydropyranyloxy group was introduced at the 3-hydroxy position of egg sphingomyelin, cholesterol was still able to condense the molecular packing of this derivative. The condensing effect of cholesterol on derivatives of N-stearoyl-SPMs was significantly larger than the comparable effect observed with 1,2-distearoyl-sn-glycero-3-phosphocholine or 1,2-dipalmitoyl-sn-glycero-3-phosphocholine. Our results with 3-hydroxysphingomyelins having differing N-acyl chain lengths (i.e., N-stearoyl, N-myristoyl, and N-lauroyl), and with 3-hydroxy-N-(alpha-hydroxypalmitoyl)sphingomyelin also indicated that cholesterol was able to induce condensation of the molecular packing.(ABSTRACT TRUNCATED AT 250 WORDS) |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|