Fluorescent sterol probes for intracellular transport, imaging, and therapeutics

Article Chemistry, Medicinal

Steroid-Quinoline Hybrids for Disruption and Reversion of Protein Aggregation Processes

Helio M. T. Albuquerque et al.

Summary: Reversing protein aggregation within cells is crucial in fighting protein-misfolding disorders, and a new family of cholesterol-quinoline hybrids has been found to effectively inhibit and disaggregate protein aggregation.

ACS MEDICINAL CHEMISTRY LETTERS (2022)

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Article Multidisciplinary Sciences

Sterolight as imaging tool to study sterol uptake, trafficking and efflux in living cells

Jarmila Kralova et al.

Summary: Understanding the subcellular localization and transport pathways of cholesterol is crucial for treating cholesterol-related diseases. However, reliable tools to monitor these processes are currently lacking. This study introduces Sterolight, a BODIPY-labelled sterol, as a suitable probe for visualizing cholesterol/lipid trafficking. The study reveals key mechanisms involved in the intracellular transport of Sterolight and highlights its potential applications in studying sterol biology.

SCIENTIFIC REPORTS (2022)

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Article Spectroscopy

BODIPY-Ethynylestradiol molecular rotors as fluorescent viscosity probes in endoplasmic reticulum

Diego Martinez-Bourget et al.

Summary: Fluorescent molecular rotors (FMRs), known for their ability to sense changes in viscosity, have been explored as potential viscosity probes. This study presents two potential BODIPY FMRs based on an ethynylestradiol spindle and evaluates their potential as FMRs through various experiments including photophysical characterization, SXRD studies, TD-DFT computations, and confocal microscopy imaging in MCF-7 cells.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY (2022)

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Review Biochemistry & Molecular Biology

Photoaffinity labeling approaches to elucidate lipid-protein interactions

Weizhi Yu et al.

Summary: In this review, recent advances in understanding the mechanisms of diazirine photocrosslinking are summarized, and an overview of the latest applications of photoaffinity labeling in revealing the interactions between diverse types of lipids and specific members of the proteome is provided.

CURRENT OPINION IN CHEMICAL BIOLOGY (2022)

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Review Biochemistry & Molecular Biology

Recent advances in estrogen receptor-targeted probes conjugated to BODIPY dyes

Linlin Gai et al.

Summary: This review focuses on the synthesis methods, optical properties, and biological activity of BODIPY fluorescent probes conjugated to estrogen receptors, providing new strategies for designing fluorescent probes targeting estrogen receptors.

STEROIDS (2022)

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Article Biochemistry & Molecular Biology

Rhenium(I) conjugates as tools for tracking cholesterol in cells

Joanna Lazniewska et al.

Summary: Cholesterol is crucial for maintaining the integrity and fluidity of cell membranes, and it serves as a precursor for the production of steroid hormones, bile acids, and vitamin D. Understanding the storage and trafficking of cholesterol within cells is essential for studying normal cell physiology and disease mechanisms.

METALLOMICS (2022)

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Article Biochemistry & Molecular Biology

Cholesterol interaction attenuates scramblase activity of SCRM-1 in the artificial membrane

Muhasin Koyiloth et al.

Summary: Phospholipid (PL) scramblases are transmembrane proteins mediating bidirectional phospholipid translocation, with a saturable cholesterol-binding domain identified in SCRM-1. Interaction with cholesterol affects scramblase activity, potentially due to the binding of cholesterol, as demonstrated by deletion and mutation studies. The C-terminal helix of SCRM-1 is crucial for membrane insertion, and the scrambling activity is modulated by cholesterol binding in the lipid bilayer.

BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES (2021)

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Article Biochemistry & Molecular Biology

Synthesis and biological evaluation of cationic TopFluor cholesterol analogues

Michal Jurasek et al.

Summary: New cationic analogues of BODIPY-Cholesterol have been discovered, with faster internalization and slightly different intracellular localization levels compared to traditional TF-Chol, showing potential for monitoring cholesterol changes in cells.

BIOORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Design, Synthesis, and Evaluation of a Luminescent Cholesterol Mimic

Emily M. Work et al.

Summary: The novel 15-azasterol has been designed and synthesized as a luminescent cholesterol mimic for monitoring cholesterol trafficking. It exhibits a brightness similar to 32-times greater than widely used probes, along with resistance to photobleaching and a large Stokes-like shift of approximately 150-200 nm. Experimental and computational studies have revealed the photophysical properties of the probe, indicating an intersystem crossing to the triplet excited state with subsequent phosphorescent decay. Additionally, molecular dynamics simulations demonstrate the structural similarity of the probe to cholesterol in its binding mode to NPC proteins.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Biochemistry & Molecular Biology

Induction of Endoplasmic Reticulum Stress-Mediated Apoptosis by Aminosteroid RM-581 Efficiently Blocks the Growth of PC-3 Cancer Cells and Tumors Resistant or Not to Docetaxel

Rene Maltais et al.

Summary: RM-581, an aminosteroid derivative, acts as an endoplasmic-reticulum stress inducer with potent anticancer activities in androgen-independent prostate cancer cells. It efficiently blocks cell proliferation and shows synergistic effects with docetaxel, while not inducing cell resistance. In vivo studies in a PC-3 xenograft tumor model demonstrate superior blockade compared to docetaxel. Additionally, RM-581 is effective in stopping cell progression in docetaxel-resistant cells and leads to alterations in gene markers and intratumoral levels of cholesterol and fatty acids.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2021)

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Article Biochemistry & Molecular Biology

Direct observation of nystatin binding to the plasma membrane of living cells

Maria Szomek et al.

Summary: Nystatin is a widely used antifungal drug that inhibits yeast infections and endocytic processes in mammalian cells. Through spectroscopic methods, its interaction with model membranes has been thoroughly investigated.

BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES (2021)

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Article Biochemistry & Molecular Biology

Spectrally and Time-Resolved Fluorescence Imaging of 22-NBD-Cholesterol in Human Peripheral Blood Mononuclear Cells in Chronic Kidney Disease Patients

Ingrid Lajdova et al.

Summary: The study investigated the interaction of the fluorescent probe 22-NBD-cholesterol with PBMC membranes, revealing its distribution in membranes and changes influenced by statin treatment in CKD patients. This suggests that 22-NBD-cholesterol could be used as a tool to study lipid metabolism changes in CKD patients undergoing statin treatment.

MOLECULES (2021)

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Article Biochemistry & Molecular Biology

Direct and specific binding of cholesterol to the mitochondrial translocator protein (TSPO) using PhotoClick cholesterol analogue

Elias Georges et al.

Summary: The study demonstrated the direct binding of PhotoClick cholesterol to TSPO, with this interaction occurring at physiologically relevant sites. Excess cholesterol was found to reduce the photolabelling of TSPO.

JOURNAL OF BIOCHEMISTRY (2021)

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Article Chemistry, Medicinal

Turning a Quinoline-based Steroidal Anticancer Agent into Fluorescent Dye for its Tracking by Cell Imaging

Rene Maltais et al.

Summary: RM-581, a potent aminosteroid derivative with cytotoxic activity against cancer cells, was modified to create a fluorescent probe RM-581-Fluo, which was found to accumulate in the endoplasmic reticulum of breast cancer cells, providing a new tool for investigating its mechanism of action.

ACS MEDICINAL CHEMISTRY LETTERS (2021)

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Article Biochemistry & Molecular Biology

Validation of Trifluoromethylphenyl Diazirine Cholesterol Analogues As Cholesterol Mimetics and Photolabeling Reagents

Kathiresan Krishnan et al.

Summary: Cholesterol analogues containing aliphatic diazirine or TPD groups were used as photoaffinity labeling reagents to study cholesterol binding sites on GLIC. The probes showed differences in photolabeling efficiencies and residues identified, indicating complementary information provided by the two classes of probes. Photoaffinity labeling using these reagents in mammalian cell membranes revealed differences in the pattern of labeled proteins, highlighting their utility in future studies of cholesterol biology.

ACS CHEMICAL BIOLOGY (2021)

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Article Chemistry, Physical

Rational design and bioimaging application of cholesterol conjugated fluorescence probe for Cu2+ detection

Chunli Zhong et al.

Summary: A new cholesterol-conjugated fluorescent probe Chol-6RN was designed for Cu2+ detection, showing improved sensitivity, linear correlation, and detection limit compared to the control probe Chol-RN. The probe was found to have negligible cytotoxicity in HeLa cells and demonstrated better sensitivity for Cu2+ detection in live cells.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY (2021)

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Article Biochemistry & Molecular Biology

3-Hexanoyl-7-nitrobenz-2-oxa-1,3-diazol-4-yl-cholesterol (3-NBD-cholesterol) is a versatile cholesterol tracer

ShuaiShuai Hu et al.

Summary: The research shows that 3-NBD-cholesterol can effectively trace cholesterol dynamics in cellular systems and exhibits versatility in different cell models and extracellular vesicles. The application of this tracer provides a new tool for studying cholesterol dynamics in cells.

STEROIDS (2021)

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Article Cell Biology

Enhanced enzymatic production of cholesteryl 6MODIFIER LETTER PRIME-acylglucoside impairs lysosomal degradation for the intracellular survival of Helicobacter pylori

Sasikala Muthusamy et al.

Summary: The study revealed that CAG enhances the internalization of H. pylori in host cells, disrupts autophagy flux, and reduces lysosomal biogenesis.

JOURNAL OF BIOMEDICAL SCIENCE (2021)

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Article Chemistry, Organic

Stress-responsive rhodamine bioconjugates for membrane-potential-independent mitochondrial live-cell imaging and tracking

Tarushyam Mukherjee et al.

Summary: By utilizing sterol-modified rhodamine, live-cell imaging of mitochondria without dependence on a membrane potential has been achieved. The sterol probes are highly biocompatible, exhibiting improved brightness, impressive contrast, and background-free tracking of mitochondrial dynamics. This study opens up possibilities for developing different sterol markers to understand cellular responses and functions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Cellular delivery of dinucleotides by conjugation with small molecules: targeting translation initiation for anticancer applications

Natalia Kleczewska et al.

Summary: Targeting cap-dependent translation initiation is a potential approach for developing novel anti-cancer therapies. Synthetic cap analogs are potent antagonists of eIF4E and delivery into cells can be facilitated by small molecule ligands like cholesterol, which also enhances interactions with eIF4E and shows cytotoxic effects towards cancer cells.

CHEMICAL SCIENCE (2021)

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Review Chemistry, Multidisciplinary

NBD-based synthetic probes for sensing small molecules and proteins: design, sensing mechanisms and biological applications

Chenyang Jiang et al.

Summary: The review focuses on NBD-based synthetic probes as advanced chemical tools for biomolecular sensing, discussing detection mechanisms, selectivity, design strategies, and biological applications of these important constructs, as well as highlighting self-assembled NBD-based probes and outlining future directions for NBD-based chemosensors. The comprehensive review aims to facilitate the development of future probes for investigating and understanding different biological processes and aid the development of potential theranostic agents.

CHEMICAL SOCIETY REVIEWS (2021)

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Article Biochemistry & Molecular Biology

Direct and specific binding of cholesterol to the mitochondrial translocator protein (TSPO) using PhotoClick cholesterol analogue

Elias Georges et al.

Summary: The study demonstrates that the translocator protein TSPO competitively interacts with a clickable photoreactive cholesterol analogue, displaying high affinity. Photo-reactive cholesterol can saturably label TSPO and be specifically detected through immunoprecipitation under specific conditions.

JOURNAL OF BIOCHEMISTRY (2021)

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Article Spectroscopy

A novel cholesterol conjugated fluorescence probe for Cu2+ detection and bioimaging in living cells

Jia Ting et al.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY (2020)

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Article Biochemistry & Molecular Biology

New 20-hydroxycholesterol-like compounds with fluorescent NBD or alkyne labels: Synthesis, in silico interactions with proteins and uptake by yeast cells

Yaroslav Faletrov et al.

CHEMISTRY AND PHYSICS OF LIPIDS (2020)

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Article Biochemistry & Molecular Biology

Imaging mitochondria and plasma membrane in live cells using solvatochromic styrylpyridines

Tarushyam Mukherjee et al.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY (2020)

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Article Chemistry, Inorganic & Nuclear

Deep-Red-Fluorescent Zinc Probe with a Membrane-Targeting Cholesterol Unit

Jin Ju Kim et al.

INORGANIC CHEMISTRY (2020)

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Article Biochemistry & Molecular Biology

Fabrication of deoxycholic acid tethered α-cyanostilbenes as smart low molecular weight gelators and AIEE probes for bio-imaging

Devesh S. Agarwal et al.

STEROIDS (2020)

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Review Chemistry, Analytical

Advances in the development of fluorescence probes for cell plasma membrane imaging

Chaolong Liu et al.

TRAC-TRENDS IN ANALYTICAL CHEMISTRY (2020)

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Article Multidisciplinary Sciences

Influence of fluorophore and linker length on the localization and trafficking of fluorescent sterol probes

Jarmila Kralova et al.

SCIENTIFIC REPORTS (2020)

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Article Biochemistry & Molecular Biology

Organization and dynamics of NBD-labeled lipids in lipid bilayer analyzed by FRET using the small membrane fluorescent probe AHBA as donor

Cassia Alessandra Marquezin et al.

BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES (2019)

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Review Biochemistry & Molecular Biology

Membrane Lipid Composition: Effect on Membrane and Organelle Structure, Function and Compartmentalization and Therapeutic Avenues

Doralicia Casares et al.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2019)

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Article Chemistry, Organic

Luminescent conjugates between dinuclear rhenium complexes and 17-ethynylestradiol: synthesis, photophysical characterization, and cell imaging

Matteo Proverbio et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

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Article Biochemistry & Molecular Biology

MemBright: A Family of Fluorescent Membrane Probes for Advanced Cellular Imaging and Neuroscience

Mayeul Collot et al.

CELL CHEMICAL BIOLOGY (2019)

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Article Chemistry, Medicinal

Design, Synthesis, and Evaluation of Orally Bioavailable Quinoline-Indole Derivatives as Innovative Multitarget-Directed Ligands: Promotion of Cell Proliferation in the Adult Murine Hippocampus for the Treatment of Alzheimer's Disease

Zhiren Wang et al.

JOURNAL OF MEDICINAL CHEMISTRY (2018)

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Article Chemistry, Multidisciplinary

Rational Design and Facile Synthesis of a Highly Tunable Quinoline-Based Fluorescent Small-Molecule Scaffold for Live Cell Imaging

Joomyung V. Jun et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Medicine, Research & Experimental

A Novel Estrogen Receptor α-Targeted Near-Infrared Fluorescent Probe for in Vivo Detection of Breast Tumor

Chu Tang et al.

MOLECULAR PHARMACEUTICS (2018)

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Article Multidisciplinary Sciences

Cholesterol-pyrene as a probe for cholesterol distribution on ordered and disordered membranes: Determination of spectral wavelengths

Claudia Almeida et al.

PLOS ONE (2018)

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Article Spectroscopy

Cholesterol: Revisiting its fluorescent journey on 200th anniversary of Chevruel's cholesterine

Arunima Chaudhuri et al.

BIOMEDICAL SPECTROSCOPY AND IMAGING (2017)

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Article Multidisciplinary Sciences

Crystal structures of translocator protein (TSPO) and mutant mimic of a human polymorphism

Fei Li et al.

SCIENCE (2015)

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Review Biochemistry & Molecular Biology

Roles and regulation of phospholipid scramblases

Karthik M. Kodigepalli et al.

FEBS LETTERS (2015)

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Article Biochemistry & Molecular Biology

Estrogen receptors alpha (ERα) and beta (ERβ): Subtype-selective ligands and clinical potential

Ilaria Paterni et al.

STEROIDS (2014)

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Review Biochemistry & Molecular Biology

Insights into the mechanisms of sterol transport between organelles

Bruno Mesmin et al.

CELLULAR AND MOLECULAR LIFE SCIENCES (2013)

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Article Biochemistry & Molecular Biology

FLIM studies of 22-and 25-NBD-cholesterol in living HEK293 cells: Plasma membrane change induced by cholesterol depletion

Pavel Ostasov et al.

CHEMISTRY AND PHYSICS OF LIPIDS (2013)

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Review Biochemical Research Methods

Fluorescence microscopy-A historical and technical perspective

Malte Renz

CYTOMETRY PART A (2013)

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Article Chemistry, Medicinal

A Fluorescent Styrylquinoline with Combined Therapeutic and Diagnostic Activities against Alzheimer's and Prion Diseases

Matteo Staderini et al.

ACS MEDICINAL CHEMISTRY LETTERS (2013)

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Article Cell Biology

Role of ORPs in Sterol Transport from Plasma Membrane to ER and Lipid Droplets in Mammalian Cells

Maurice Jansen et al.

TRAFFIC (2011)

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Review Multidisciplinary Sciences

Lipid Rafts As a Membrane-Organizing Principle

Daniel Lingwood et al.

SCIENCE (2010)

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Article Biophysics

A Novel Fluorescent Probe That Senses the Physical State of Lipid Bilayers

Hirotaka Sasaki et al.

BIOPHYSICAL JOURNAL (2009)

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Article Cardiac & Cardiovascular Systems

Caveolin-1 and regulation of cellular cholesterol homeostasis

Philippe G. Frank et al.

AMERICAN JOURNAL OF PHYSIOLOGY-HEART AND CIRCULATORY PHYSIOLOGY (2006)

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Article Biochemistry & Molecular Biology

Oxidation of unsaturated phospholipids in membrane bilayer mixtures is accompanied by membrane fluidity changes

JW Borst et al.

BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS (2000)

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Fluorescent sterol probes for intracellular transport, imaging, and therapeutics

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