WO2013039307A2 - Composé fluorescent à haut rendement et son procédé de préparation - Google Patents

Composé fluorescent à haut rendement et son procédé de préparation Download PDF

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WO2013039307A2
WO2013039307A2 PCT/KR2012/007133 KR2012007133W WO2013039307A2 WO 2013039307 A2 WO2013039307 A2 WO 2013039307A2 KR 2012007133 W KR2012007133 W KR 2012007133W WO 2013039307 A2 WO2013039307 A2 WO 2013039307A2
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group
heteroatom
formula
alkoxy
alkyl
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PCT/KR2012/007133
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English (en)
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WO2013039307A3 (fr
Inventor
Seong Keun Kim
Seung Bum Park
Il Seung Yang
Eun Ha Kim
Jun Hee Kang
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Snu R&Db Foundation
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Priority claimed from KR1020120083374A external-priority patent/KR101294993B1/ko
Application filed by Snu R&Db Foundation filed Critical Snu R&Db Foundation
Priority to US14/344,585 priority Critical patent/US10787607B2/en
Publication of WO2013039307A2 publication Critical patent/WO2013039307A2/fr
Publication of WO2013039307A3 publication Critical patent/WO2013039307A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00—Radiation therapy
    • A61N5/06—Radiation therapy using light
    • A61N5/0613—Apparatus adapted for a specific treatment
    • A61N5/062—Photodynamic therapy, i.e. excitation of an agent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a new fluorescent compound having high efficiency, a method for preparing the same, and its use.
  • Luminescence means the emission of light having a wavelength which correspond to the energy difference when a substance is converted to a stable state having low energy from an unstable state having high energy.
  • Various sources of energy such as light, chemical reactions, heat, electricity, cathode-emitted electron or the like may be used. Said difference sources of energy produce different types of light emission such as photo-, chemi-, thermo-, electro-, cathodo-luminecence, or the like.
  • Luminescence can be classified as fluorescence and phosphorescence. Fluorescence refers to the phenomenon that a substance emits light only when the substance is irradiated, and phosphorescence refers to the phenomenon that a substance continuously emits a light even after the irradiation to the substance is ended.
  • a substance emitting fluorescence is referred to as a fluorescent element or a fluorescent substance.
  • Such fluorescent substance can be divided into a single-photon absorption fluorescent substance which absorbs only one photon under a strong laser to emit the fluorescence and a multi-photon absorption fluorescent substance which absorbs a plurality of photons to emit the fluorescence.
  • the present invention relates to a new fluorescent compound simultaneously having a single-photon absorption fluorescent feature as well as a multi-photon absorption fluorescent feature, in particular, 2-photon absorption fluorescent feature.
  • the present invention was completed by finding a new fluorescent compound of ( E )-4-(6,8-dihydroxynaphthalen-2-yl)but-3-en-2-one (hereinafter, referred to as resveratrone ) having a high single-photon absorptive efficiency and/or 2-photon absorptive efficiency after a photochemical reaction of a conventionally known resveratrol which is frequently found in peanuts, grapes, berries and the like.
  • resveratrone a new fluorescent compound of ( E )-4-(6,8-dihydroxynaphthalen-2-yl)but-3-en-2-one
  • the purpose of the present invention is to provide a new fluorescent compound with high efficiency having single-photon absorptive characteristics and/or two-photon absorptive characteristics.
  • the purpose of the present invention is to provide a method of preparing the above fluorescent compound.
  • the purpose of the present invention is to provide the use of the fluorescent compound having single-photon absorptive characteristics and/or two-photon absorptive characteristics.
  • the present invention provides resveratrone [(E)-4-(6,8-dihydroxynaphthalen-2-yl)but-3-en-2-one] and its derivatives as a new fluorescent compound and a method for preparing the same by a photochemical reaction of resveratrol and its derivatives which are not fluorescent.
  • R is naphthyl group ( ), anthracenyl group ( ) or phenalenyl group ( ),
  • naphthyl, anthracenyl or phenalenyl group can be each independently substituted with at least one substituent selected from the group consisting of hydroxy; halogen; straight-chain or branched C 1 -C 10 alkyl; C 3 -C 6 cycloalkyl; straight-chain or branched C 1 -C 6 alkoxy; C 2 -C 6 heterocycloalkyl comprising N, O and/or S as heteroatom; phenyl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of halogen atom, amino group, nitrile group, nitro group, C 1 -C 10 alkyl group, C 2 -C 10 alkenyl group, C 1 -C 10 alkoxy group, C 3 -C 6 cyclaoalkyl group, C 2 -C 6 heterocycloalkyl group comprising N, O or S as heteroatom, C 6 -C 16 aryl group, and C
  • each of R 1 is independently hydrogen atom; halogen, straight-chain or branched C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, straight-chain or branched C 1 -C 6 alkoxy; C 2 -C 6 heterocycloalkyl comprising N, O and/or S as heteroatom; phenyl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of halogen atom, amino group, nitrile group, nitro group, C 1 -C 10 alkyl group, C 2 -C 10 alkenyl group, C 1 -C 10 alkoxy group, C 3 -C 6 cyclaoalkyl group, C 2 -C 6 heterocycloalkyl group comprising N, O or S as heteroatom, C 6 -C 16 aryl group, and C 5 -C 15 heteroaryl group comprising N, O and/or S as heteroatom;
  • R 4 is substituted or unsubstituted phenyl group ( ) or substituted or unsubstituted naphthyl group ( ),
  • said phenyl or naphthyl group can be each independently substituted with at least one substituent selected from the group consisting of hydroxy; halogen; straight-chain or branched C 1 -C 10 alkyl; C 3 -C 6 cycloalkyl; straight-chain or branched C 1 -C 6 alkoxy; C 2 -C 6 heterocycloalkyl comprising N, O and/or S as heteroatom; phenyl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of halogen atom, amino group, nitrile group, nitro group, C 1 -C 10 alkyl group, C 2 -C 10 alkenyl group, C 1 -C 10 alkoxy group, C 3 -C 6 cyclaoalkyl group, C 2 -C 6 heterocycloalkyl group comprising N, O or S as heteroatom, C 6 -C 16 aryl group, and C 5 -C 15 heteroaryl
  • a display element comprising the organic fluorescent compound of (3).
  • the new fluorescent compound of the present invention has single-photon absorptive characteristics and/or two-photon absorptive characteristics as well as no or little toxicity according to a cytotoxicity test.
  • Fig. 1 is a graph showing emission spectra of the reactant compounds and the fluorescent compound finally produced of the present invention (wherein the highly fluorescent species is denoted by X).
  • Fig. 2 is a graph showing a single-photon emission spectrum (left) and a two-photon emission spectrum (right) of the fluorescent compound of the present invention.
  • Fig. 3 is graph showing a change of single-photon emission spectra of the fluorescent compound finally of the present invention.
  • Fig. 4 is a photograph showing two-photon emission of the fluorescent compound of the present invention.
  • Fig. 5 is a HPLC graph for the reaction products obtained after different durations of exposure to UV irradiation (wherein the highly fluorescent species is denoted by X).
  • Fig. 6 is a graph showing the comparison of the intensity versus wavelength of the fluorescent compounds which have been produced in the presence of ascorbic acid and in the absence of ascorbic acid, respectively.
  • Fig. 7 is a graph showing the comparison of the intensity versus wavelength of the fluorescent compounds which have been produced under N 2 atmosphere (N 2 purging) and not, respectively.
  • Fig. 8 is a graph showing an excitation spectrum of the reactant compound and an emission spectrum of the fluorescent compound finally produced in Example 10 of the present invention.
  • Fig. 9 is a graph showing an excitation spectrum of the reactant compound and an emission spectrum of the fluorescent compound finally produced in Example 11 of the present invention.
  • Fig. 10 is a graph showing an excitation spectrum of the reactant compound and an emission spectrum of the fluorescent compound finally produced in Example 12 of the present invention.
  • Fig. 11 is a graph showing an excitation spectrum of the reactant compound and an emission spectrum of the fluorescent compound finally produced in Example 13 of the present invention.
  • Fig. 12 is the photo images showing the result of Cytomorphology Test for a blank test (Control), a fluorescent compound of the present invention (Resveratrone) and a comparative compound(a commercial anticancer agent, Etoposide ).
  • Fig. 13 is a graph showing the result of Blue Exclusion Test for a blank test (Control), a fluorescent compound of the present invention (Resveratrone) and a comparative compound ( Etoposide ).
  • Fig. 14 is a graph showing the result of Western Blotting Test for a blank test (Control), a fluorescent compound of the present invention (Resveratrone) and a comparative compound ( Etoposide ).
  • the present invention provides a new fluorescent compound represented by the following formula 1:
  • R is naphthyl group ( ), anthracenyl group ( ) or phenalenyl group ( ),
  • naphthyl, anthracenyl or phenalenyl group can be each independently substituted with at least one substituent selected from the group consisting of hydroxy; halogen; straight-chain or branched C 1 -C 10 alkyl; C 3 -C 6 cycloalkyl; straight-chain or branched C 1 -C 6 alkoxy; C 2 -C 6 heterocycloalkyl comprising N, O and/or S as heteroatom; phenyl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of halogen atom, amino group, nitrile group, nitro group, C 1 -C 10 alkyl group, C 2 -C 10 alkenyl group, C 1 -C 10 alkoxy group, C 3 -C 6 cyclaoalkyl group, C 2 -C 6 heterocycloalkyl group comprising N, O or S as heteroatom, C 6 -C 16 aryl group, and C
  • each of R 1 is independently hydrogen atom; halogen, straight-chain or branched C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, straight-chain or branched C 1 -C 6 alkoxy; C 2 -C 6 heterocycloalkyl comprising N, O and/or S as heteroatom; phenyl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of halogen atom, amino group, nitrile group, nitro group, C 1 -C 10 alkyl group, C 2 -C 10 alkenyl group, C 1 -C 10 alkoxy group, C 3 -C 6 cyclaoalkyl group, C 2 -C 6 heterocycloalkyl group comprising N, O or S as heteroatom, C 6 -C 16 aryl group, and C 5 -C 15 heteroaryl group comprising N, O and/or S as heteroatom; preferably, selected from the group consisting of hydrogen
  • the present invention provides a fluorescent compound represented by any one of the following formulae 2 ⁇ 6:
  • R 2 and R 3 are each independently selected from a group consisting of hydrogen atom; hydroxy; halogen; straight-chain or branched C 1 -C 10 alkyl; C 3 -C 6 cycloalkyl; straight-chain or branched C 1 -C 6 alkoxy; C 2 -C 6 heterocycloalkyl comprising N, O and/or S as heteroatom; phenyl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of halogen atom, amino group, nitrile group, nitro group, C 1 -C 10 alkyl group, C 2 -C 10 alkenyl group, C 1 -C 10 alkoxy group, C 3 -C 6 cyclaoalkyl group, C 2 -C 6 heterocycloalkyl group comprising N, O or S as heteroatom, C 6 -C 16 aryl group, and C 5 -C 15 heteroaryl group comprising N, O and/or S as heteroatom
  • the present invention provides a method of preparing a fluorescent compound represented by formula 1 above.
  • a fluorescent compound represented by formula 1 above is prepared via a method comprises a step of dissolving a compound represented by the following Formula 7, a compound represented by the following Formula 8 or a mixture thereof in water, an organic solvent or mixture thereof and a step of subjecting to a UV irradiation:
  • R 4 is substituted or unsubstituted phenyl group ( ) or substituted or unsubstituted naphthyl group ( ),
  • said phenyl or naphthyl group can be each independently substituted with at least one substituent selected from the group consisting of hydroxy; halogen; straight-chain or branched C 1 -C 10 alkyl; C 3 -C 6 cycloalkyl; straight-chain or branched C 1 -C 6 alkoxy; C 2 -C 6 heterocycloalkyl comprising N, O and/or S as heteroatom; phenyl group which is unsubstituted or substituted with at least one substituent selected from the group consisting of halogen atom, amino group, nitrile group, nitro group, C 1 -C 10 alkyl group, C 2 -C 10 alkenyl group, C 1 -C 10 alkoxy group, C 3 -C 6 cyclaoalkyl group, C 2 -C 6 heterocycloalkyl group comprising N, O or S as heteroatom, C 6 -C 16 aryl group, and C 5 -C 15 heteroaryl
  • organic solvent which can be used in the present invention
  • protic solvents such as ethanol, methanol, n-propanol, iso-propanol, n-butanol, DMSO (dimethyl sulfoxide), EA (ethyl ester), THF (tetrahydrofuran) and the like, which can be used alone or as a mixture thereof.
  • Ethanol, methanol, n-propanol, iso-propanol, n-butanol or DMSO are preferable, and DMSO is most preferable.
  • the reaction mixture can additionally include an antioxidant such as, for example, ascorbic acid, polyphenols, glutathione, N-acetylcystein, -tocopherol, butylated hydroxyanisole (BHA), catechin, quercetin, uric acid, bilirubin, glucose, flavonoid or the like, which can be added alone or as mixture thereof, after dissolving a compound represented by Formula 7, a compound represented by Formula 8 or a mixture thereof in water or an organic solvent, and before subjecting to an UV irradiation.
  • an antioxidant such as, for example, ascorbic acid, polyphenols, glutathione, N-acetylcystein, -tocopherol, butylated hydroxyanisole (BHA), catechin, quercetin, uric acid, bilirubin, glucose, flavonoid or the like, which can be added alone or as mixture thereof, after dissolving a compound represented by Formula 7, a compound represented by Formula 8 or a mixture thereof
  • the reaction in order to improve the yield of the product, the reaction can be conducted under N 2 atmosphere (N 2 purging).
  • the reaction temperature at the photochemical reaction can be selected from -10 ⁇ 100 °C, particularly 0 and 60 °C, preferably between 10 and 40 °C, and more preferably between 20 and 30 °C.
  • the wavelength of UV ray to be irradiated can be selected from 100 ⁇ 500 nm, preferably 200 ⁇ 400 nm, and more preferably 250 ⁇ 450 nm.
  • the irradiation time can be selected from 5 second ⁇ 50 minutes, particularly 6 second ⁇ 40 minutes, preferably 8 seconds ⁇ 30 minutes, and more preferably 10 seconds ⁇ 20 minutes.
  • the reaction temperature, UV wavelength and irradiation time is not strictly limited to the above ranges and can be easily modified according to the purpose.
  • the fluorescent compound of the present invention prepared by the above method has high efficiency single-photon absorptive characteristics and/or two-photon absorptive characteristics ( see Figs. 2 ⁇ 4).
  • the fluorescent compound of the present invention can be utilized in an organic fluorescent element including a fluorescent compound as well as in a display element including an organic fluorescent elements.
  • the display element can be a plasma display panel, a cathode-ray tube (CRT), a lamp, or the like.
  • the fluorescent compound according to the present invention does not have toxicity to a cell which can be verified by a cytotoxicity test ( see Figs. 12 ⁇ 14 and Test Examples 1 ⁇ 3). Thus, it can be used as an organic fluorescent element directed to a specific target in cells.
  • the fluorescent compound according to the present invention can be usefully utilized in the field of a spectrometer, a two-photon absorptive storing device, a laser micro processing apparatus, a photo dynamic therapy apparatus or the like.
  • HRMS high-resolution mass spectrometry
  • LTQ orbitrab high-resolution mass spectrometry
  • HRMS analysis is conducted using a High-Resolution Liquid Chromatography/Tandem Mass Analysis equipment located at the National Instrumentation Center for Environmental Management of Seoul National University.
  • UV absorption of the final fluorescent compound is determined by using a UV-VISIBLE spectrophotometer (Perkin Elmer, USA). Maximum values of excitation and emission are determined by using a fluorescent spectrophotometer (PTI, USA).
  • the absolute quantum yield is determined by using an absolute PL quantum yield measurement system (QE-1000, Otsuka Electronics, Japan).
  • the relative quantum yield is determined by measuring the absorbance and emission intensity for each five concentrations for one solvent, determining the slope of said measured values, and comparing the slope with that of rhodamin 6G (the quantum yield of rhodamin 6G in ethanol is 0.95).
  • trans -Resveratrol and trans -pterostilbene are commercially available (from sigma-Aldlich and TCI, respectively). Other solvents and organic samples are purchased in the market and used without any additional purification unless there is any other description. Distilled water is completed by ion exchange and filtration.
  • the fluorescent compound is obtained from trans -resveratrol in the same manner as Example 1. Quantum yields of each organic solvent are shown in Table 1.
  • the fluorescent compound is obtained from trans -resveratrol in the same manner as Example 1.
  • the emission spectra of the obtained compound is shown in Fig. 3, wherein the time of 0 min, 2 min and 4 min means the UV irradiation, thus the spectrum at 0 min is for the reactant ( trans -pterostilbene).
  • the final compound prepared from a non-fluorescent compound of trans -pterostilbene is a fluorescent compound.
  • the fluorescent compound is obtained from trans -resveratrol in the same manner as Example 1.
  • Fig. 6 shows each graph of intensity versus wavelength of the final product obtained with adding ascorbic acid and the final product obtained without adding ascorbic acid. As can be seen in Fig. 6, it can be understood that the intensity of the final product obtained with adding ascorbic acid is higher than that obtained without adding ascorbic acid.
  • the fluorescent compound is obtained from trans -resveratrol in the same manner as Example 1.
  • Fig. 7 shows each graph of intensity versus wavelength of the final product obtained with conducting under N 2 atmosphere and the final product obtained without conducting under N 2 atmosphere. As can be seen in Fig. 7, it can be understood that the intensity of the final product obtained with conducting under N 2 atmosphere is higher than that obtained without conducting under N 2 atmosphere.
  • a cell line is cultured for a certain period of time (about 72 hours) and then a cytotoxicity test is conducted.
  • a cytotoxicity test is conducted as a control group.
  • a blank test is conducted in the same manner as above without adding any compound including the test compound and the comparative compound.
  • a test compound Resveratrone, the fluorescent compound obtained in Example 1
  • a comparative compound Etoposide , a commercial anticancer agent
  • Fig. 12 shows each microscopic photo image of the resulting breast epithelial cells after cultured in a blank test (control group, left) and in the presence of the test fluorescent compound ( Resveratrone, center) or the comparative compound ( Etoposide , right), respectively.
  • the comparative compound ( Etoposide ) results to a remarkable reduction in the number of cells in comparison with the control group, while the test compound ( Resveratrone ) has no significant difference from the control group.
  • test compound ( Resveratrone ) of the present invention has no or little cell toxicity and very high stability in comparison with the commercial anticancer agent ( Etoposide ).
  • Fig. 13 is a graph showing the result of Blue Exclusion Test for the control group (blank), the test compound (resveratrone) and the comparative compound (etoposide), respectively.
  • the test compound (left side) results to a number of cells similar to that of the control group in both test concentrations (1 ⁇ M and 10 ⁇ M), while the comparative compound (right side) results to a remarkably reduced number of cells in both test concentrations (1 ⁇ M and 10 ⁇ M).
  • test compound ( Resveratrone ) of the present invention has no or little cell toxicity and a very high stability in comparison with the commercial anticancer agent ( Etoposide ).
  • a breast epithelial cell line is cultured in a blank test (control group) and in the presence of a test compound ( Resveratrone ), respectively, and an osteosarcoma cell line (U2OS) is cultured in the presence of a comparative compound ( Etoposide ).
  • the degree of cell extinction is evaluated by examining the degree of expression of extinction and damage of a specific factor by using Western Blotting Test and the result is shown in Fig. 14.
  • the blank test left side, Control group , concentration of 0 ⁇ M
  • the test compound center side, Resveratrone , three concentrations of 1, 10 and 100 ⁇ M
  • the comparative compound (right side, Etoposide , concentration of 10 ⁇ M) shows a significantly remarkable peak at 17kDa, 19kDa and 89kDa positions which result from cell extinction and damage, by which it can be understood that a lot of cells are extinguished and/or damaged.
  • test compound ( Resveratrone ) of the present invention has no or little cell toxicity.
  • the new fluorescent compound of the present invention can be usefully utilized in the field of organic fluorescent element, display element, spectrometer, two-photon absorptive storing device, laser micro processing apparatus, photo dynamic therapy apparatus and the like.

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  • Engineering & Computer Science (AREA)
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Abstract

Cette invention concerne une resvératrone fluoresccente, [(E)-4-(6,8-dihydroxynaphthalén-2-yl)but-3-én-2-one] et ses dérivés de Formule 1 et un procédé pour les préparer par réaction photochimique du resvératrol et de ses dérivés de Formule 7 ou de Formule 8 qui ne sont pas fluorescents. Les nouveaux composés fluorescents selon l'invention ont des caractéristiques d'absorption à un photon et/ou des caractéristiques d'absorption à deux photons ainsi qu'une toxicité nulle ou faible selon un essai de cytotoxicité qui leur permettent d'être utilisés de manière utile dans le domaine des éléments fluorescents organiques, des éléments d'affichage, des spectromètres, des dispositifs de stockage par absorption à deux photons, des appareils de microtraitement par laser, des appareils de thérapie photodynamiques et autres.
PCT/KR2012/007133 2011-09-16 2012-09-05 Composé fluorescent à haut rendement et son procédé de préparation WO2013039307A2 (fr)

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KR20110093191 2011-09-16
KR10-2011-0093191 2011-09-16
KR10-2012-0083374 2012-07-30
KR1020120083374A KR101294993B1 (ko) 2011-09-16 2012-07-30 고효율 형광 화합물 및 그의 제조 방법

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10787607B2 (en) 2011-09-16 2020-09-29 Snu R&Db Foundation High efficiency fluorescent compound and method for preparing the same

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KR20090041632A (ko) * 2007-10-24 2009-04-29 한국생명공학연구원 생체분자 표지용 수용성 광변색 화합물 및 이를 이용한생체분자의 검출방법
US20100081724A1 (en) * 2007-01-30 2010-04-01 Andre Arigony Souto Process of obtainment of trans-resveratrol and/or emodin and nutraceuticcal compositions containing them

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US20100081724A1 (en) * 2007-01-30 2010-04-01 Andre Arigony Souto Process of obtainment of trans-resveratrol and/or emodin and nutraceuticcal compositions containing them
KR20090041632A (ko) * 2007-10-24 2009-04-29 한국생명공학연구원 생체분자 표지용 수용성 광변색 화합물 및 이를 이용한생체분자의 검출방법

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KIM, H. M. ET AL.: 'Two-Photon Fluorescent Turn-On Probe for Lipid Rafts in Live Cell and Tissue' JOURNAL OF THE AMERICAN CHEMICAL SOCIETY vol. 130, no. 13, 2008, pages 4246 - 4247 *
KIM, S. ET AL.: 'Photochemical generation of a new, highly fluorescent compound from non-fluorescent resveratrol' CHEMICAL COMMUNICATIONS vol. 48, no. 32, 24 February 2012, pages 3839 - 3841 *
LEMHADRI, M. ET AL.: 'Palladium-catalyzed Heck reactions of alk-1-en-3-ones with aryl bromides: a very simple access to (E)-1-arylalk-1-en-3-ones' SYNTHESIS vol. 6, 2009, pages 1021 - 1035 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10787607B2 (en) 2011-09-16 2020-09-29 Snu R&Db Foundation High efficiency fluorescent compound and method for preparing the same

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