کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1357428 981251 2016 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Incorporation of fluorophore–cholesterol conjugates into liposomal and mycobacterial membranes
ترجمه فارسی عنوان
ترکیب کلیه های فلوروفورا کلسترول به غشاهای لیپوزوم و میکروسکوپیک
کلمات کلیدی
فلورسانس، قاچاق کلسترول، حمل و نقل غشاء، بیماری سل
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
چکیده انگلیسی

Fluorescently-labeled steroids that emit intense blue light in nonpolar solvent (λem (CH2Cl2) ≈ 440 nm, ΦF = 0.70) were prepared by treating cholesteryl chloroformate with 4-amino-1,8-naphthalimides. The lipid portion of the conjugates embeds into liposomal membrane bilayers in minutes, leaving the fluorophore exposed to the external aqueous environment. This causes a 40-nm red-shift in λem and significant quenching. DFT optimizations predict the conjugates to be about 30 Å long when fully extended, but rotation about the linker group can bring the compounds into an ‘L’-shape. Such a conformation would allow the cholesteryl anchor to remain parallel to the acyl chains of a membrane while the fluorescent group resides in the interfacial region, instead of extending beyond it. When incubated with Mycobacterium smegmatis mc2 155, a bacterial species known to use natural cholesterol, the labeled steroids support growth and can be found localized in the membrane fraction of the cells using HPLC. These findings demonstrate stable integration of fluorescent cholesterols into bacterial membranes in vivo, indicating that these compounds may be useful for evaluating cholesterol uptake in prokaryotic organisms.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry - Volume 24, Issue 5, 1 March 2016, Pages 1045–1049
نویسندگان
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