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    Area of Science:

    • Cell Biology
    • Biophysics
    • Medicinal Chemistry

    Background:

    • Understanding subcellular cholesterol trafficking is crucial for cell biology and medicine.
    • Existing fluorescent cholesterol analogs have limitations in mimicking natural cholesterol behavior.

    Purpose of the Study:

    • To develop and characterize novel fluorescent cholesterol analogs (CNDs) based on a bifunctional 1,8-naphthalimide scaffold.
    • To investigate the structure-function relationships of CNDs, focusing on head group and linker modifications.
    • To evaluate the ability of CNDs to mimic natural cholesterol behavior at molecular and cellular levels.

    Main Methods:

    • Synthesis of CNDs with varying head groups and linkers.
    • Solvatochromic behavior assessment in organic solvents and model membranes.
    • All-atom molecular dynamics simulations to compare CNDs with cholesterol in membranes.
    • Investigation of probe partitioning in giant unilamellar vesicles.
    • Evaluation of cellular uptake, distribution, and subcellular localization in mouse fibroblasts and astrocytes.

    Main Results:

    • CNDs were categorized into neutral, charged, and hydroxyl-containing groups.
    • Molecular dynamics simulations and membrane partitioning studies revealed how CNDs interact with model membranes.
    • Cellular uptake and distribution varied by cell type and were influenced by head group modifications.
    • CNDs demonstrated distinct spectral, biophysical, and cellular targeting features.

    Conclusions:

    • The modular design of CNDs allows for facile creation of fluorescent cholesterol probes with tunable properties.
    • These CNDs serve as a valuable toolkit for investigating subcellular cholesterol distribution and trafficking.
    • The findings contribute to a better understanding of cholesterol dynamics in biological systems.