A triterpene oleanolic acid conjugate with 3-hydroxyflavone derivative as a new membrane probe with two-color ratiometric response

Türkmen, Zeynep; Klymchenko, Andrey S.; Oncul, Sule; Duportail, Guy; Topcu, Gülaçtı; Demchenko, Alexander P.

doi:10.1016/j.jbbm.2005.03.008

Cited by 17 publications

(8 citation statements)

References 42 publications

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“…They are especially significant for sphingomyelin bilayers due to their capability of forming very rigid structures, “rafts”, with cholesterol molecules. We produced sphingomyelin bilayers with embedded functional 3HC dyes, and observed dramatic changes in florescence color upon incorporation of cholesterol molecules into these bilayer structures [32]. These experiments were reproduced with the application of a number of different dyes and the results of one of them are depicted in Fig.…”

Section: Protein Labeling and Incorporation Into Nanostructuresmentioning

confidence: 92%

Visualization and sensing of intermolecular interactions with two‐color fluorescent probes

Demchenko

2006

FEBS Letters

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We developed a new generic fluorescence sensing technology based on the change of relative intensities between two well-separated emission bands of the novel functional 3-hydroxychromone (3HC) dyes. A greatly enhanced self-calibrating wavelength-ratiometric response is obtained to all major types of non-covalent interactions that can be used in sensingto polarity, hydrogen bonding ability and to local electrostatic fields. This technology may find a broad range of applications -from homogeneous assays in solutions to microarrays, microfluidic devices, nanosensors and whole cell imaging systems. It allows transforming micelles or phospholipid vesicles into nanosensor devices. In cellular research a high sensitivity to membrane potentials can be obtained and the membrane changes during apoptosis detected.

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Section: Protein Labeling and Incorporation Into Nanostructuresmentioning

confidence: 92%

Visualization and sensing of intermolecular interactions with two‐color fluorescent probes

Demchenko

2006

FEBS Letters

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“…By comparison with published spectral data, the isolated triterpenoids were determined as arjunic acid (1), rosamultic acid (2), haptadienic acid (3), 1β-hydroxyeuscaphic acid (4), euscaphic acid (5), tormentic acid (6), pomolic acid 7, ursolic acid (8), and oleanolic acid (9), respectively (l " Fig. 1) [23][24]. HPLC analysis also demonstrated that the EtOAc-soluble fraction was triterpenoid-rich (l " Fig.…”

mentioning

confidence: 99%

Lipopolysaccharide-Induced Nitric Oxide and Prolyl Oligopeptidase – Inhibitory Activities of Triterpenoids from Sanguisorba officinalis

Zhang

et al. 2016

PMIO

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!Lipopolysaccharide-induced nitric oxide and the protease prolyl oligopeptidase (EC 3.4.21.26) have been proposed as targets for the treatment of cognitive disturbances such as dementia. In this study, nine triterpenoids isolated from the roots of Sanguisorba officinalis, including arjunic acid (1), rosamultic acid (2), haptadienic acid (3), 1β-hydroxyeuscaphic acid (4), euscaphic acid (5), tormentic acid (6), pomolic acid (7), ursolic acid (8), and oleanolic acid (9), were tested in vitro for their inhibitory activities on lipopolysaccharide-induced nitric oxide in N9 microglia cells and on prolyl oligopeptidase. Among them, 7 exhibited the strongest inhibitory activity on lipopolysaccharide-induced nitric oxide (IC 50 , 21.9 µM), while 8 and 9 exhibited a significant prolyl oligopeptidase inhibitory activity (IC 50 18.1 and 24.0 µM, respectively). The results could provide a clue that these triterpenoids are responsible for the reported neuro-protective effect of S. officinalis. Key wordsSanguisorba officinalis · Rosaceae · triterpenoids · lipopolysaccharide-induced nitric oxide · prolyl oligopeptidaseThe dried roots of Sanguisorba officinalis L. (Rosaceae) are used in traditional Chinese medicine for the treatment of disorders such as bleeding, burns, ulcerative colitis, and chronic intestinal infections, due to their hemostatic, anti-infective, antibacterial, and anti-inflammatory activities [1][2][3][4][5][6][7][8]. Previous chemical investigations of S. officinalis revealed the existence of triterpenes, triterpenoids, saponins and polyphenols [3][4][5][6]. Moreover, S. officinalis and its active component (catechin) have been reported to possess potential neuroprotective effects and antioxidant activities [3][4][5][6][7][8]. Our interest in the constituents possibly responsible for these beneficial properties inspired us to undertake a further biological investigation of S. officinalis. Nitric oxide (NO) released by N9 microglia (stimulated by lipopolysaccharide; LPS) is known as a neurotoxic factor and has a great influence on the cell viability of microglia. Microglia, the resident macrophage-like cells in the brain, have been proposed to play a pivotal role in the immune surveillance of the central nervous system [9]. Furthermore, lines of evidence showed that microglia-mediated neuroinflammation contributes to the pathology of both acute pathologies such as stroke or traumatic brain injury and chronic neurodegenerative diseases [10][11][12]. The protease prolyl oligopeptidase (POP; EC 3.4.21.26) has been proposed to play an important role in the neuropeptide metabolism and to be a target for the treatment of cognitive disturbances such as dementia [13][14][15]. It has been postulated that specific POP inhibitors could protect nerve cells, prevent memory loss, and enhance cognition [16][17][18]. Therefore, POP inhibitors have been developed as candidate drugs for the treatment of various clinical conditions of the brain [19]. Some natural POP inhibitors, especially triterpenoids from medical pl...

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“…3-HF emission is governed by an excited-state intramolecular proton transfer (ESIPT) process and these probes demonstrate very strong solvatochromism and electrochromism [72][73][74]. These 3-HF fluorophores thus exhibit dual band fluorescence emission which is sensitive to environmental factors, and as a sensor/probe they have a clear advantage over single band fluorophores [75][76][77][78][79][80]. One of these bands originates from the normal excited state (N*), and the other is due to the ESIPT reaction product tautomer (T*).…”

Section: Water Sorptionmentioning

confidence: 99%

Fluorescence Analysis of Thermoresponsive Polymers

Morris

Ryder

2015

Reviews in Fluorescence

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The use of microscale thin polymer films is widespread in biomedical science and engineering, with applications in areas such as tissue engineering, drug delivery, microfluidic devices, bio-adhesion mediators, and bio-actuators. Much attention is devoted to the use of functional polymers that display stimuliresponsive behavior with the intention of providing "smart" coatings. One potential example is the use of thin thermoresponsive polymer films as drug eluting coatings on medical devices, where not only does the polymer function as a drug reservoir but it also acts as a biocompatibility modulator to improve device performance.Often these thin polymer coatings have to be applied to complex geometries, which can cause problems for in-situ analysis. Another important consideration is the fact that these films have large surface area to mass ratios and thus water uptake can be significant. This is serious because coating stability, device efficacy, and long-term storage are influenced by the physiochemical properties of the polymer which are modulated by water content. Thus, there is a need for a rapid, non-contact, non-destructive, analytical method capable of analyzing thermoresponsive polymers in solution, and in-situ of the solid-state on medical devices. Fluorescence spectroscopy based methods can deal with both sample types and provide additional benefits in terms of high sensitivity and low probe concentrations, which provide for minimal sample disruption. This article gives a brief overview of the application of various fluorescence methods for the physicochemical characterization of thermoresponsive polymers such as poly (N-isopropylacrylamide), PNIPAm.

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A triterpene oleanolic acid conjugate with 3-hydroxyflavone derivative as a new membrane probe with two-color ratiometric response

Cited by 17 publications

References 42 publications

Visualization and sensing of intermolecular interactions with two‐color fluorescent probes

Visualization and sensing of intermolecular interactions with two‐color fluorescent probes

Lipopolysaccharide-Induced Nitric Oxide and Prolyl Oligopeptidase – Inhibitory Activities of Triterpenoids from Sanguisorba officinalis

Fluorescence Analysis of Thermoresponsive Polymers

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