A structural model for the cholesterol‐phosphatidylcholine complexes in bilayer membranes

Huang, Chunbo

doi:10.1007/bf02533637

Cited by 217 publications

(82 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There is almost no laurate-laurate packing. Most importantly, the packing of the laurate A and B chains with the cholesteryl groups might be relevant to the structural arrangement when cholesterol is incorporated in phospholipid bilayers (Huang, 1977). Bond lengths and angles for cholesteryl laurate molecules A and B are consistent with those found in cholesteryl acetate (Sawzik & Craven, 1979), and in related crystal structures (Craven & Guerina, 1979b;Guerina & Craven, 1979;Craven & DeTitta, 1976).…”

Section: Resultssupporting

confidence: 61%

The crystal structure of cholesteryl laurate at 298 K

Sawzik¹,

Craven²

1979

Acta Crystallogr Sect B

View full text Add to dashboard Cite

Cholesteryl laurate, C39H6802, is monoclinic, space group P2~ with cell dimensions a = 12.989 (8), b = 9.008 (5), c = 32.020 (14) A, fl = 91.36 (5) °, and Z = 4 (two molecules in the asymmetric unit, A, B). Integrated intensities with I > 2a(I) were measured with a diffractometer for 1346 reflections at room temperature. The structure was solved using Patterson rotation and translation methods. Blockdiagonal least-squares refinement gave R = 0.104. The C(17) cholesterol side chains and ester groups have almost fully extended conformations in both molecules A and B. The greatest conformational difference in the two molecules comes from a difference of 48 ° in the rotation at the ester bond. Molecular packing in the crystal structure of cholesteryl laurate is isostructural with that of cholesteryl nonanoate. The ester chains are packed with cholesteryl ring systems so as to provide a model for the molecular associations of cholesterol in biological membranes.

show abstract

Section: Resultssupporting

confidence: 61%

The crystal structure of cholesteryl laurate at 298 K

Sawzik¹,

Craven²

1979

Acta Crystallogr Sect B

View full text Add to dashboard Cite

show abstract

“…It has been proposed in the past that the sterol hydroxyl group would play an essential role in hydrogen bridge formation between sterol and phospholipid [30][31][32]. There is, however, no experimental support for a direct interaction between phospholipid and sterol.…”

Section: Discussionmentioning

confidence: 99%

The effect of the sterol oxygen function on the interaction with phospholipids

Demel

Lala

Kumari

et al. 1984

Biochimica et Biophysica Acta (BBA) - Biomembranes

View full text Add to dashboard Cite

The effect of cholesteryi ethers (namely cholesteryl methyl ether, cholesteryi ethyl ether, cholesteryl n-propyl ether, cholesteryi isopropyl ether, cholesteryi butyl ether, cholesteryl methoxymethyl ether, cholesteryl (2'-hydroxy)-3-ethyl ether) and cholesteryl ester (namely cholesteryi acetate) is tested on the interaction with phosphatidylcholines in liquid-crystalline and crystalline state. The interfacial properties of sterols are tested at the air-water interface. The cholesteryl ethers show a reduced interracial stability with increasing hydrophobicity of the ether-linked moiety. The interaction between the sterol derivatives and phospholipids in mixed monolayers is indicated by measuring the deviation from the simple addivity rule (condensing effect). An interaction is found only for cholesteryl (2'-hydroxy)-3-ethyl ether, cholesteryl methyl ether and cholesteryl ethyl ether. These sterols also reduce the glucose permeability of liposomal membranes in this order. In this respect cholesteryl (2'-hydroxy)-3-ethyl ether is as effective as cholesterol. Cholesteryl methyl ether and cholesteryl ethyl ether show 62 and 33 percent of the effect observed with cholesterol. The effect of the sterol derivatives on the gel-to-liquid-crystalline phase transition of dipalmitoylphosphatidylcholine is measured by differential scanning calorimetry. Cholesteryl methyl ether, cholesteryl ethyl ether, and cholesteryl (2'-hydroxy)-3-ethyl ether reduce the energy content of the phase transition nearly as effective as cholesterol, cholesteryl n-propyl ether has only a small effect. Although cholesteryl acetate, and cholesteryl methoxymethyl ether have no condensing or permeability-reducing effect, they have a considerable effect on the gel-to-liquid-crystalline phase transition. Cholesteryi isopropyl ether and cholesteryl butyl ether have no effect. It is concluded that a free 30-hydroxy group is not a prerequisite to observe a sterol-like effect in membranes. However, the interfacial stability and the orientation of the sterol and oxygen moiety at the sterol 3-position are important.

show abstract

“…Ergosta-8,14-dien-3,8-ol, the sterol that accumulates in treated sporidia, may not be released from the carrier protein, or if it does enter the membrane structure, the sterol may not interact effectively with the acyl hydrocarbon moieties of phospholipids due to the absence of axial hydrogens at C-9 and C-14 of the sterol nucleus (13).…”

Section: Discussionmentioning

confidence: 99%

Mode of Action of the Azasteroid Antibiotic 15-Aza-24-Methylene- d -Homocholesta-8,14-Dien-3β-ol in Ustilago maydis

Woloshuk

Sisler

Dutky

1979

Antimicrob Agents Chemother

View full text Add to dashboard Cite

Ustilago maydis sporidia treated with 0.1 μg of azasterol (15-aza-24-methylene- d -homocholesta-8,14-dien-3β-ol) per ml appeared branched and vacuolated after 6 h of incubation. Sporidial multiplication, dry weight increase, and synthesis of protein, deoxyribonucleic acid, and ribonucleic acid were only slightly or moderately inhibited during the initial 3 h of incubation. An increase of free fatty acids was observed in lipid extracts of treated sporidia after incubation for 3 h or more. Ergosterol synthesis was completely inhibited within 1 h and there was a gradual decline of ergosterol content during 6 h which was accompanied by an accumulation of the sterol intermediate ergosta-8,14-dien-3β-ol. The results indicate that toxicity of the azasterol results from specific inhibition of the reduction of the sterol C-14(15) double bond. A triarimol-tolerant strain of Cladosporium cucumerinum was tolerant to the azasterol, but an imazalil-tolerant strain of Aspergillus nidulans was not.

show abstract

A structural model for the cholesterol‐phosphatidylcholine complexes in bilayer membranes

Cited by 217 publications

References 50 publications

The crystal structure of cholesteryl laurate at 298 K

The crystal structure of cholesteryl laurate at 298 K

The effect of the sterol oxygen function on the interaction with phospholipids

Mode of Action of the Azasteroid Antibiotic 15-Aza-24-Methylene- d -Homocholesta-8,14-Dien-3β-ol in Ustilago maydis

Contact Info

Product

Resources

About