N-(2-Naphthyl)-23,24-dinor-5-cholen-22-amin-3β-ol, a fluorescent cholesterol analog

Kao, Yin J.; Soutar, Anne K.; Hong, Kong-Yi; Pownall, Henry J.; Smith, Louis C.

doi:10.1021/bi00606a036

Cited by 29 publications

(15 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The absence of anisotropy changes rules out aggregation of dehydroergosterol below 5 mol % dehydroergosterol. This interpretation is also consistent with data reported by others (Kao et al, 1978) using another fluorescent sterol analogue, N-(2-naphthy1)-23,24-dinor-5-cholen-22-amin-3/3-01. The fluorescent properties of this fluorescent sterol were also solvent polarity sensitive.…”

Section: Discussionsupporting

confidence: 93%

A fluorescence study of dehydroergosterol in phosphatidylcholine bilayer vesicles

Schroeder¹,

Barenholz²,

Gratton³

et al. 1987

Biochemistry

View full text Add to dashboard Cite

Section: Discussionsupporting

confidence: 93%

A fluorescence study of dehydroergosterol in phosphatidylcholine bilayer vesicles

Schroeder¹,

Barenholz²,

Gratton³

et al. 1987

Biochemistry

View full text Add to dashboard Cite

“…Moreover, cholesterol decreases lipid chain mobility, thus reducing structural defects and therefore the space in wlfich water molecules can be accommodated [23]. Kao et al [24] have shown that the presence of cholesterol reduces the apparent polarity of the hydrocarbon region of the phospholipid bilayer. In unsaturated phosphatidylcholine, Davenport et al [25] have shown that DPH is located in the central part of the bilayer.…”

Section: Discussionmentioning

confidence: 99%

Effect of cholesterol on membrane microheterogeneity: a study using 1,6-diphenyl-1,3,5-hexatriene fluorescence lifetime distributions

Fiorini

Gratton

Curatola

1989

Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metaboli

View full text Add to dashboard Cite

“…Among cholesterol analogs with attached reporter groups, derivatives with N-(7nitrobenz-2-oxa-1,3-diazol-4-yl) (N-NBD) [9], 1-pyrenylmethoxycarbonyl [10] or 3pyrenylamino [11] fluorophores in the side chain have been developed. However, because the lifetime of the NBD fluorophore depends on the medium polarity and pH in a complex way, and the lifetime of the pyrenyl excited state is quite long, these probes are not well suited to studies where fluorescence anisotropy is to be measured in membranes.…”

Section: Introductionmentioning

confidence: 99%

New fluorescent cholesterol analogs as membrane probes

Grechishnikova

Bergström

Johansson

et al. 1999

Biochimica et Biophysica Acta (BBA) - Biomembranes

View full text Add to dashboard Cite

New fluorescent cholesterol analogs, (22E, 20R)-3beta-hydroxy-23-(9-anthryl)-24-norchola-5,22-die ne (R-AV-Ch), and the 20S-isomer (S-AV-Ch) were synthesized, their spectral and membrane properties were characterized. The probes bear a 9-anthrylvinyl (AV) group instead of C22-C27 segment of the cholesterol alkyl chain. Computer simulations show that both of the probes have bulkier tail regions than cholesterol and predict some perturbation in the packing of membranes, particularly for R-AV-Ch. In monolayer experiments, the force-area behavior of the probes was compared with that of cholesterol, pure and in mixtures with palmitoyloleoyl phosphatidylcholine (POPC) and N-stearoyl sphingomyelin (SSM). The results show that pure R-AV-Ch occupies 35-40% more cross-sectional area than cholesterol at surface pressures below film collapse (0-22 mN/m); whereas S-AV-Ch occupies nearly the same molecular area as cholesterol. Isotherms of POPC or SSM mixed with 0.1 mol fraction of either probe are similar to isotherms of the corresponding mixtures of POPC or SSM with cholesterol. The probes show typical AV absorption (lambda 386, 368, 350 and 256 nm) and fluorescence (lambda 412-435 nm) spectra. Steady-state anisotropies of R-AV-Ch and S-AV-Ch in isotropic medium or liquid-crystalline bilayers are higher than the values obtained for other AV probes reflecting hindered intramolecular mobility of the fluorophore and decreased overall rotational rate of the rigid cholesterol derivatives. This suggestion is confirmed by time-resolved fluorescence experiments which show also, in accordance with monolayer data, that S-AV-Ch is better accommodated in POPC-cholesterol bilayers than R-AV-Ch. Model and natural membranes can be labeled by either injecting the probes via a water-soluble organic solvent or by co-lyophilizing probe and phospholipid prior to vesicle production. Detergent-solubilization studies involving 'raft' lipids showed that S-AV-Ch almost identically mimicked the behavior of cholesterol and that of R-AV-Ch was only slightly inferior. Overall, the data suggest that the AV-labeled cholesterol analogs mimic cholesterol behavior in membrane systems and will be useful in related studies.

show abstract

N-(2-Naphthyl)-23,24-dinor-5-cholen-22-amin-3β-ol, a fluorescent cholesterol analog

Cited by 29 publications

References 45 publications

A fluorescence study of dehydroergosterol in phosphatidylcholine bilayer vesicles

A fluorescence study of dehydroergosterol in phosphatidylcholine bilayer vesicles

Effect of cholesterol on membrane microheterogeneity: a study using 1,6-diphenyl-1,3,5-hexatriene fluorescence lifetime distributions

New fluorescent cholesterol analogs as membrane probes

Contact Info

Product

Resources

About