- OXAZINE-BASED WATER-SOLUBLE FLUOROPHORE COMPOUNDS FOR IN VIVO NERVE IMAGING
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This invention provides novel oxazine-based, water soluble fluorophore compounds useful in in vivo nerve imaging, as well as compositions comprising them and methods for their use.
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Page/Page column 36-38
(2021/07/10)
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- NERVE-SPECIFIC FLUOROPHORE FORMULATIONS FOR DIRECT AND SYSTEMIC ADMINISTRATION
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Nerve-specific fluorophore formulations of Formula (I) for direct or systemic administration are described. The formulations can be used in fluorescence-guided surgery (FGS) to aid in nerve preservation during surgical interventions.
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Page/Page column 24-26
(2021/08/13)
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- NEAR-INFRARED NERVE-SPARING FLUOROPHORES
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Provided are far red to near-infrared nerve-sparing fluorescent compounds, compositions comprising them, and methods of their use in medical procedures.
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Page/Page column 41-42
(2020/02/17)
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- NERVE-SPECIFIC FLUOROPHORE FORMULATIONS FOR DIRECT AND SYSTEMIC ADMINISTRATION
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Nerve-specific fluorophore formulations for direct or systemic administration are described. The formulations can be used in fluorescence-guided surgery (FGS) to aid in nerve preservation during surgical interventions.
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Paragraph 0150; 0152
(2020/03/02)
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- Structural modifications of nile red carbon monoxide fluorescent probe: Sensing mechanism and applications
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Carbon monoxide (CO) is a cell-signaling molecule (gasotransmitter) produced endogenously by oxidative catabolism of heme, and the understanding of its spatial and temporal sensing at the cellular level is still an open challenge. Synthesis, optical properties, and study of the sensing mechanism of Nile red Pd-based CO chemosensors, structurally modified by core and bridge substituents, in methanol and aqueous solutions are reported in this work. The sensing fluorescence "off-on" response of palladacycle-based sensors possessing low-background fluorescence arises from their reaction with CO to release the corresponding highly fluorescent Nile red derivatives in the final step. Our mechanistic study showed that electron-withdrawing and electron-donating core substituents affect the rate-determining step of the reaction. More importantly, the substituents were found to have a substantial effect on the Nile red sensor fluorescence quantum yields, hereby defining the sensing detection limit. The highest overall fluorescence and sensing rate enhancements were found for a 2-hydroxy palladacycle derivative, which was used in subsequent biological studies on mouse hepatoma cells as it easily crosses the cell membrane and qualitatively traces the localization of CO within the intracellular compartment with the linear quantitative response to increasing CO concentrations.
- Klán, Petr,Madea, Dominik,Martínek, Marek,Muchová, Lucie,Váňa, Ji?í,Vítek, Libor
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p. 3473 - 3489
(2020/03/25)
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- Acrylamide-Coumarin-Benzaldehyde as a Turn-on Fluorescent Probe Providing an Enhanced Water Solubility for Detection of Cysteine and Homocysteine
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We presented an acrylamide conjugated coumarin (1) as a fluorescent probe for detection of cysteine (Cys) and homocysteine (Hcy). Probe 1 is composed of coumarin as a fluorophore, acrylamide as a reactive site to Cys/Hcy, and benzaldehyde for improvement of the water solubility. To Cys/Hcy, the acrylamide group of 1 readily undergoes Michael addition resulting in a strong fluorescence at 420 nm through an inhibition of photo-induced electron transfer (PET). The turn-on fluorescence change of 1 was observed for Cys and Hcy, but not seen for other biologically abundant thiols (e.g., glutathione, H2S), reactive oxygen and nitrogen species, anions, and metal ions. Moreover, 1 can give strong fluorescence upon the addition of Cys and Hcy in wide pH range and their limits of detection for Cys and Hcy turned out to be 17.25 and 8.69 μM, respectively.
- Chang, Min Jung,Joo, Jin Hui,Lee, Min Hee
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p. 539 - 543
(2019/05/07)
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- Tuning thiol addition to squaraines by ortho-substitution and the use of serum albumin
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Tuning the reactivity of squaraine dyes toward nucleophilic addition of thiols was investigated. A series of water soluble, aniline-derived squaraines were synthesized with various ortho substitutions to the squaraine ring. As hypothesized, we found that placing moderately electron donating groups in the ortho position conveyed intermediate reactivity to thiols between the essentially non-reactive hydroxyl-substituted squaraines and very reactive non-substituted squaraines. Furthermore, serum albumin was tested for its influence on the addition of thiols to the squaraines. The dyes bind in the hydrophobic cavities of the protein, and thus we expected serum albumin to affect the squaraines' reactivity. Rather than a protective effect by the protein, we found a cooperative effect for thiol addition.
- Diehl, Katharine L.,Bachman, J. Logan,Anslyn, Eric V.
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p. 316 - 324
(2017/03/02)
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- Synthesis and photophysical studies of new benzo[a]phenoxazinium chlorides as potential antifungal agents
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A set of four new benzo[a]phenoxazinium chlorides possessing ethyl, propyl, decyl and tetradecyl groups at the 9-amino function of the heterocycle along with a propyl group at the 5-amino position was efficiently synthesized. These compounds displayed fluorescence with maximum emission wavelengths of 673 and 685?nm, in anhydrous ethanol and water. All the benzo[a]phenoxazines were evaluated against the yeast Saccharomyces cerevisiae in a broth microdilution assay. It was found that their antifungal activity depended on the variation in the lengths of the aliphatic chains. The highest MIC activity of 1.56?μM was obtained for compound 7 comprising a di-alkylated propyl substituent at 9-amino position and a propyl chain at the 5-amino position of the heterocycle core.
- Leit?o, M. Inês P.S.,Raju, B. Rama,Naik, Sarala,Coutinho, Paulo J.G.,Sousa, Maria Jo?o,Gon?alves, M. Sameiro T.
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supporting information
p. 3936 - 3941
(2016/08/09)
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- Biomaker for mitochondrial target and hyperthermia using the same
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The present invention relates to a marker for a mitochondrial target and a hyperthermo-treating method using the same, represented by Chemical formula 1 or Chemical formula 2. According to the present invention, when near-infrared ray is irradiated, a temperature of mitochondria is increased to allow the mitochondria to become extinct, thereby inhibiting a tumor.(AA) Compound of [Chemical formula3] + 2.0 W/cm^2(BB) Compound of [Chemical formula3] + 6.0 W/cm^2(CC,FF) Compound of [Chemical formula3] + 10 W/cm^2(EE) Compound of [Chemical formula3] + 6 W/cm^2COPYRIGHT KIPO 2016
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Paragraph 0058; 0059; 0061; 0063
(2017/05/16)
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- BODIPY-Coumarin Conjugate as an Endoplasmic Reticulum Membrane Fluidity Sensor and Its Application to ER Stress Models
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An endoplasmic reticulum (ER) membrane-selective chemosensor composed of BODIPY and coumarin moieties and a long alkyl chain (n-C18) was synthesized. The emission ratio of BODIPY to coumarin depends on the solution viscosity. The probe is localized to the ER membrane and was applied to reveal the reduced ER membrane fluidity under ER stress conditions.
- Lee, Hoyeon,Yang, Zhigang,Wi, Youngjin,Kim, Tae Woo,Verwilst, Peter,Lee, Yun Hak,Han, Ga-In,Kang, Chulhun,Kim, Jong Seung
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p. 2474 - 2480
(2015/12/24)
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- Enhanced NIR radiation-triggered hyperthermia by mitochondrial targeting
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Mitochondria are organelles that are readily susceptible to temperature elevation. We selectively delivered a coumarin-based fluorescent iron oxide nanoparticle, Mito-CIO, to the mitochondria. Upon 740 nm laser irradiation, the intracellular temperature of HeLa cells was elevated by 2.1 °C within 5 min when using Mito-CIO, and the treatment resulted in better hyperthermia and a more elevated cytotoxicity than HeLa cells treated with coumarin iron oxide (CIO), which was missing the mitochondrial targeting unit. We further confirmed these results in a tumor xenograft mouse model. To our knowledge, this is the first report of a near-infrared laser irradiation-induced hyperthermic particle targeted to mitochondria, enhancing the cytotoxicity in cancer cells. Our present work therefore may open a new direction in the development of photothermal therapeutics.
- Jung, Hyo Sung,Han, Jiyou,Lee, Jae-Hong,Lee, Ji Ha,Choi, Jong-Min,Kweon, Hee-Seok,Han, Ji Hye,Kim, Jong-Hoon,Byun, Kyung Min,Jung, Jong Hwa,Kang, Chulhun,Kim, Jong Seung
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p. 3017 - 3023
(2015/03/18)
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- A self-calibrating bipartite viscosity sensor for mitochondria
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A self-calibrating bipartite viscosity sensor 1 for cellular mitochondria, composed of coumarin and boron-dipyrromethene (BODIPY) with a rigid phenyl spacer and a mitochondria-targeting unit, was synthesized. The sensor showed a direct linear relationship between the fluorescence intensity ratio of BODIPY to coumarin or the fluorescence lifetime ratio and the media viscosity, which allowed us to determine the average mitochondrial viscosity in living HeLa cells as ca. 62 cP (cp). Upon treatment with an ionophore, monensin, or nystatin, the mitochondrial viscosity was observed to increase to ca. 110 cP.
- Yang, Zhigang,He, Yanxia,Lee, Jae-Hong,Park, Nayoung,Suh, Myungkoo,Chae, Weon-Sik,Cao, Jianfang,Peng, Xiaojun,Jung, Hyosung,Kang, Chulhun,Kim, Jong Seung
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supporting information
p. 9181 - 9185
(2013/07/26)
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- Anticancer drug release from a mesoporous silica based nanophotocage regulated by either a one- or two-photon process
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An excellent mesoporous silica nanoparticle (MSN) based drug deliver system (DDS) was reported for regulated anticancer drug release upon the irradiation of either one- or two-photon excitation. In this system, the coumarin grafted on MSN acted as both the "phototrigger" for the drug release and fluorescence group for cell luminescence imaging. External light manipulations such as changing irradiation wavelength, intensity, and time can regulate the release of the anticancer drug precisely. Biological studies in vitro suggest that the drug carrier can effectively deliver the anticancer drug into intracellular environs and, hence, promote the drug action to kill the cancer cells upon irradiation. We envision that the good biocompatibility, cellar uptake property, and efficient photoregulated drug release will be of great benefit to future controlled release in vivo biomedical applications.
- Lin, Qiuning,Huang, Qi,Li, Chunyan,Bao, Chunyan,Liu, Zhenzhen,Li, Fuyou,Zhu, Linyong
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supporting information; experimental part
p. 10645 - 10647
(2010/11/16)
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- Water-soluble nile blue derivatives: syntheses and photophysical properties
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Four water-soluble 2-hydroxy-Nile Blue derivatives, 1a, 1b, 2a, and 2b, were prepared by condensation reactions performed under relatively mild conditions (90°C, N,N-dimethylformamide with no added acid). These fluorescent probes had more favorable fluorescence characteristics than two known water-soluble Nile Blue derivatives. Specifically, they were superior to the known dyes with respect to their quantum yields in aqueous media and the sharpness of their fluorescence emissions. Concentration-dependant UV absorption and fluorescence emission studies indicated that the dyes did not aggregate in aqueous solution at concentrations of less than 1-4 μM. The new water-soluble materials 1a, 1b, 2a, and 2b emit in a desirable region of the fluorescence spectrum (A = 670-675 nm). Overall they are potentially interesting for labeling biomolecules in aqueous environments.
- Jose, Jiney,Ueno, Yuichiro,Burgess, Kevin
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supporting information; experimental part
p. 418 - 423
(2009/06/19)
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- A practical and one-pot procedure for the synthesis of 3-amino-2- cyclohexen-1-one from 3-aminophenol
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A simple, totally catalytic, and environmentally benign process for the synthesis of 3-amino-2-cyclohexen-1-one using 10% Pd/C-catalyzed hydrogenation has been developed.
- Sajiki, Hironao,Ikawa, Takashi,Hirota, Kosaku
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p. 219 - 220
(2012/12/24)
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- Substituted 4H-chromenes and analogs as activators of caspases and inducers of apoptosis and the use thereof
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The present invention is directed to substituted 4H-chromenes and analogs thereof, represented by the general Formula I: 1wherein R1-R5, A, Y and Z are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.
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- Process for producing N,N-disubstituted aminophenol
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A process for producing N,N-disubstituted aminophenol which comprises the steps of: obtaining a reaction mixture containing N-substituted aminophenol by reacting a dihydric phenol and an amine; subjecting said reaction mixture to heat treatment so as to thermally decompose quaternary ammonia salt contained in said reaction mixture into a dihydric phenol and an amine, and removing at least said amine by distillation; separating high-boiling impurities by distillation to separate N-substituted aminophenol; and subjecting said separated N-substituted aminophenol to reduction alkylation using an aldehyde compound. According to the present invention, high-purity N,N-disubstituted aminophenol can be obtained in a high yield at high selectivity, and a reduction catalyst can be used repeatedly because its activity can be maintained at a high level and yet it can retain high activity for a long period of time.
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- Method of producing N-alkylaminophenols
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N-alkyl amino phenols, such as N-ethyl-m-amino phenol are produced in high yield and with high purity by reacting a divalent phenol, such as resorcinol, with an alkylamine, such as ethylamine, in the absence of catalyst and solvent, at a temperature of 120°-210° C. under elevated pressure in an inert gas atmosphere. In a first embodiment, the resulting reaction mixture is acidified to convert the N-alkylaminophenol to its water soluble salt and the resulting aqueous layer is separated from the oily layer. The aqueous layer is rendered alkaline to liberate N-alkylaminophenol as an oily layer. The N-alkyl-aminophenol oily layer is then separated from the aqueous layer and distilled. In an alternative embodiment, the reaction mixture resulting from the reaction between the divalent phenol and alkylamine is combined with an aqueous solution of an alkali to convert unreacted phenol to its water soluble salt while the product N-alkylaminophenol remains in an oily phase which is separated from the aqueous phase. An organic solvent is used as an extractant. The recovered N-alkylaminophenol organic solution is then distilled to recover N-alkylaminophenol. Purities of the recovered N-alkylaminophenol in excess of 95% can be achieved.
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- The autorecycling oxidation of benzylamine by synthetic 8-hydroxy-5-deazaflavin derivatives
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Various 8-hydroxy-5-deazaflavin derivatives were synthesized as the model compounds of coenzyme F420. These compounds oxidized benzylamine to benzaldehyde more efficiently than the corresponding 8-unsubstituted 5-deazaflavin.
- Hirayama,Kawase,Kimachi,Tanaka,Yoneda
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p. 1255 - 1259
(2007/10/02)
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- Hydroxylation directe d'anilines en aminophenols
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Anilines react with hydrogen peroxide in SbF5-HF to give aminophenols.The formation of the products can be accounted for by the reaction of the electrophile H3O2+ on the anilinium ions.For compounds 1a-4a, the reaction yields three possible aminophenols, the meta isomer being the major product.The process is more selective with ortho toluidine 5a and para toluidine 6a, giving aminophenol(s) 5c (42percent)) and 5e (21percent), and 6c (71percent), respectively.With meta toluidine 7a, only aminophenol 7d (35percent) can be isolated from the complex reaction mixture, ring substitution pattern of the substrate favoring para hydroxylation.
- Jacquesy, Jean-Claude,Jouannetaud, Marie-Paule,Morellet, Guy,Vidal, Yves
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p. 625 - 629
(2007/10/02)
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- DIRECT CONVERSION OF ANILINES INTO AMINOPHENOLS
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Hydroxylation of anilines by hydrogen peroxide in SbF5-HF yields the three possible aminophenols, the meta isomer being the major product.The reaction implies attack of protonated hydrogen peroxide H3O2(1+) on the N-protonated substrate.
- Jacquesy, Jean-Claude,Jouannetaud, Marie-Paule,Morellet, Guy,Vidal, Yves
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p. 1479 - 1482
(2007/10/02)
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