A curcumin-based molecular probe for near-infrared fluorescence imaging of tau fibrils in Alzheimer's disease

Park, Kwang‐Su; Seo, Yujin; Kim, Mi Kyoung; Kim, Kyungdo; Kim, Yun Kyung; Choo, Hyunah; Chong, Youhoon

doi:10.1039/c5ob01847a

Cited by 48 publications

(44 citation statements)

References 22 publications

(24 reference statements)

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“…The enhanced stable fluorescence of CUASL can be used as bioimaging tool for the diagnostic purpose. Curcumin and its analogues have been established as a fluorescent biomarker for confocal imaging [ 39 ] by uptake studies inside mammalian cells [ 40 – 44 ]. Curcumin is not yet reported as a biomarker for bacterial cells.…”

Section: Introductionmentioning

confidence: 99%

Photophysical studies on curcumin-sophorolipid nanostructures: applications in quorum quenching and imaging

Vasudevan

Prabhune

2018

R. Soc. open sci.

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Sophorolipid biosurfactants are biodegradable, less toxic and FDA approved. The purified acidic form of sophorolipid is stimuli-responsive with self-assembling properties and used for solubilizing hydrophobic drugs. This study encapsulated curcumin (CU) with acidic sophorolipid (ASL) micelles and analysed using photophysical studies like UV-visible spectroscopy, photoluminescence (PL) spectroscopy and time-correlated single photon counting (TCSPC). TEM images have revealed ellipsoid micelles of approximately 100 nm size and were confirmed by dynamic light scattering. The bacterial fluorescence uptake studies showed the uptake of formed CUASL nanostructures into both Gram-positive and Gram-negative bacteria. They also showed quorum quenching activity against Pseudomonas aeruginosa. The results have demonstrated this system has potential theranostic applications.

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Section: Introductionmentioning

confidence: 99%

Photophysical studies on curcumin-sophorolipid nanostructures: applications in quorum quenching and imaging

Vasudevan

Prabhune

2018

R. Soc. open sci.

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“…It is worth mentioning that near-infrared fluorescence imaging has become a powerful tool to improve the diagnosis of diseases and also for monitoring biological activities as it represents a non-invasive imaging tool [ 39 ]. Therefore, both compounds resemble the set of fluorescent tools or dyes with imaging application reported in the literature [ 5 , 9 , 11 , 32 , 36 ].…”

Section: Resultsmentioning

confidence: 99%

“…a Molar extinction coefficient (ε) and b quantum yield (Φ) were determined at room temperature. Quinine sulfate is reference (Φr = 0.55 in H 2 SO 4 1N) [ 37 ], * taken from reference [ 5 ].…”

Section: Figures Scheme and Tablesmentioning

confidence: 99%

Non-Cytotoxic Dibenzyl and Difluoroborate Curcuminoid Fluorophores Allow Visualization of Nucleus or Cytoplasm in Bioimaging

et al. 2020

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Curcumin, the most important secondary metabolite isolated from Curcuma longa, is known for its numerous purported therapeutic properties and as a natural dye. Herein, based on curcumin’s intrinsic fluorescence, a search for improved curcumin-based fluorophores was conducted. Within the set of semi-synthetic curcumin derivatives i.e. mono (1), di (2), tri (3), tetra (4) benzylated and dibenzyl-fluoroborate (5), the fluorescence properties of 2 and 5 in solution outstood with a two-fold quantum yield compared to curcumin. Furthermore, all benzylated derivatives showed a favorable minimal cytotoxic activity upon screening at 25 μM against human cancer and non-tumoral COS-7 cell lines, with a reduction of its cytotoxic effect related to the degree of substitution. Fluorophores 2 and 5 are versatile bioimaging tools, as revealed by Confocal Fluorescence Microscopy (CFM), and showed permeation of living cell membranes of astrocytes and astrocytomas. When 2 is excited with a 405- (blue) or 543-nm (green) laser, it is possible to exclusively and intensively visualize the nucleus. However, the fluorescence emission fades as the laser wavelength moves towards the red region. In comparison, 5 allows selective visualization of cytoplasm when a 560-nm laser is used, showing emission in the NIR region, while it is possible to exclusively observe the nucleus at the blue region with a 405-nm laser.

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“…Park et al [119] developed curcumin-based NIR fluorescent probe of tau fibrils, bystructurally modifying the curcumin scaffold. As prerequisite, the curcumin derivative ought to preserve its binding affinity to the tau fibrils, and as a consequence, the probe should present significant fluorescent properties.…”

Section: Imaging Probes For Tau Tangles Detectionmentioning

confidence: 99%

Curcumin in Health and Diseases: Alzheimer’s Disease and Curcumin Analogues, Derivatives, and Hybrids

Chainoglou

Hadjipavlou‐Litina

2020

IJMS

103

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Worldwide, Alzheimer’s disease (AD) is the most common neurodegenerative multifactorial disease influencing the elderly population. Nowadays, several medications, among them curcumin, are used in the treatment of AD. Curcumin, which is the principal component of Curcuma longa, has shown favorable effects forsignificantly preventing or treating AD. During the last decade, the scientific community has focused their research on the optimization of therapeutic properties and on the improvement of pharmacokinetic properties of curcumin. This review summarizes bibliographical data from 2009 to 2019 on curcumin analogues, derivatives, and hybrids, as well as their therapeutic, preventic, and diagnostic applications in AD. Recent advances in the field have revealed that the phenolic hydroxyl group could contribute to the anti-amyloidogenic activity. Phenyl methoxy groups seem to contribute to the suppression of amyloid-β peptide (Aβ42) and to the suppression of amyloid precursor protein (APP) andhydrophobic interactions have also revealed a growing role. Furthermore, flexible moieties, at the linker, are crucial for the inhibition of Aβ aggregation. The inhibitory activity of derivatives is increased with the expansion of the aromatic rings. The promising role of curcumin-based compounds in diagnostic imaging is highlighted. The keto-enol tautomerism seems to be a novel modification for the design of amyloid-binding agents. Molecular docking results, (Q)SAR, as well as in vitro and in vivo tests highlight the structures and chemical moieties that are correlated with specific activity. As a result, the knowledge gained from the existing research should lead to the design and synthesis ofinnovative and multitargetedcurcumin analogues, derivatives, or curcumin hybrids, which would be very useful drug and tools in medicine for both diagnosis and treatment of AD.

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A curcumin-based molecular probe for near-infrared fluorescence imaging of tau fibrils in Alzheimer's disease

Cited by 48 publications

References 22 publications

Photophysical studies on curcumin-sophorolipid nanostructures: applications in quorum quenching and imaging

Photophysical studies on curcumin-sophorolipid nanostructures: applications in quorum quenching and imaging

Non-Cytotoxic Dibenzyl and Difluoroborate Curcuminoid Fluorophores Allow Visualization of Nucleus or Cytoplasm in Bioimaging

Curcumin in Health and Diseases: Alzheimer’s Disease and Curcumin Analogues, Derivatives, and Hybrids

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