- An upconversion nanoparticle with orthogonal emissions using dual nir excitations for controlled two-way photoswitching
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Developing multicolor upconversion nanoparticles (UCNPs) with the capability of regulating their emission wavelengths in the UV to visible range in response to external stimuli can offer more dynamic platforms for applications in high-resolution bioimaging, multicolor barcoding, and driving multiple important photochemical reactions, such as photoswitching. Here, we have rationally designed single-crystal core-shell-structured UCNPs which are capable of orthogonal UV and visible emissions in response to two distinct NIR excitations at 808 and 980 nm. The orthogonal excitation- emission properties of such UCNPs, as well as their ability to utilize low-power excitation, which attenuates any local heating from the lasers, endows the UCNPs with great potential for applications in materials and biological settings. As a proof of concept, the use of this UCNP for the efficient regulation of the two-way photoswitching of spiropyran by using dual wavelengths of NIR irradiation has been demonstrated.
- Zhang, Yixiao,Pasquale, Nicholas,Lee, Ki-Bum
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Read Online
- Microwave synthesis of quaternary ammonium salts
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The microwave synthesis of several quaternary ammonium salts is described. The synthesis provides comparable or better yields than published methods with reduced reaction times and in the absence of solvent.
- Winstead, Angela J.,Fleming, Nicole,Hart, Krystal,Toney, Deveine
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Read Online
- Efficient Synthesis of Chiral Indolines using an Imine Reductase from Paenibacillus lactis
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An enzymatic process for the efficient asymmetric reduction of 3H-indoles as well as 3H-indole iodides was developed for the first time. Using a new imine reductase identified from Paenibacillus lactis (PlSIR), various chiral indolines were facilely synthesized in good yields and excellent enantiopurities (up to >99% ee) under mild reaction conditions.
- Li, Hao,Luan, Zheng-Jiao,Zheng, Gao-Wei,Xu, Jian-He
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Read Online
- Multiplex cancer cell detection by SERS nanotags with cyanine and triphenylmethine Raman reporters
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SERS nanotags have been prepared to accomplish the multiplex detection of cancer cells. Herein we evaluated the adequacy of lipoic acid-containing cyanine derivatives (Cy3LA and Cy5LA) to function as multiplex partners with a triphenylmethine Raman reporter (B2LA) under a single excitation wavelength. SERS experiments enabled the multiplex recognition of two different cancer cells with antibody-conjugated nanotags that were derivatized with optimized cyanine and triphenylmethine reporters.
- Maiti, Kaustabh Kumar,Samanta, Animesh,Vendrell, Marc,Soh, Kiat-Seng,Olivo, Malini,Chang, Young-Tae
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Read Online
- Acridinium-conjugated aromatic heterocycles as highly potent FtsZ inhibitors: Design, synthesis, and biological evaluation
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The epidemic of multidrug resistance (MDR) is a serious threat to public health, and new classes of antibiotics with novel mechanisms of action are in critical need. We rationally designed and efficiently synthesized three series of new chemical entities with potential antibacterial activity targeting filamenting temperature-sensitive mutant Z (FtsZ). Evaluation of these compounds against a panel of Gram-positive bacteria including MDR and vancomycin-resistant Enterococcus?strains indicated that most compounds showed enhanced antibacterial efficacy, comparable or even superior to the reference drugs. The newly synthesized compounds proved to be substrates of the Escherichia coli efflux pump AcrB, thus affecting the activity. Their structure–activity relationships?were summarized in detail. The most potent compound 10f quickly eliminated bacteria in a bactericidal mode, with low susceptibility to induce bacterial resistance. Further mechanistic studies with the BsFtsZ protein revealed that 10f functioned as an effective FtsZ inhibitor through altering the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which leads to inhibition of cell division and cell death. Besides, 10f not only displayed no obvious cytotoxicity to mammalian cells but also had a high efficacy in a murine model of bacteremia in vivo. Regarded as a whole, our findings highlight 10f as a promising new FtsZ-targeting bactericidal agent.
- Chen, Weijin,Guo, Ting,Ma, Shutao,Ma, Yangchun,Song, Di,Zhang, Nan,Zhang, Shenyan
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- O-nitrophenyl ethanol derivative as well as preparation method and application thereof
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The invention discloses an o-nitrophenethyl alcohol derivative and a preparation method and application thereof, the structural formula of the o-nitrophenethyl alcohol derivative is shown in the specification, and R is C1-C18 alkyl. The invention provides
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Paragraph 0045; 0062-0065
(2021/04/17)
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- Co-delivery of Cu(I) chelator and chemotherapeutics as a new strategy for tumor theranostic
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Chelating Cu from tumors has been verified as an effective and promising strategy for cancer therapy through antiangiogenesis. However, systematic removal Cu by injecting with Cu chelators will result unavoidable side effects, since Cu is indispensable to the body. In this work, a micelle targeting to tumors' newborn vessels based on a polypeptide was developed to co-load DOX and Probe X, which can go through an “OFF-to-ON” procedure to report the Cu+-capture events in vivo in a real-time way by giving near infrared (NIR) fluorescence and photoacoustic signal. By co-delivering antiangiogenesis and chemotherapeutic reagents, the tumor can be significantly suppressed, meanwhile with a low systematic toxicity. Hopefully, this work can offer new insights in designing sophisticated antitumor strategy.
- Chen, Hongyi,Chen, Qinjun,Chu, Yongchao,Guo, Qin,Guo, Zhongyuan,Jiang, Chen,Jiang, Liping,Li, Chao,Liu, Peixin,Sun, Tao,Yu, Haijun,Zhang, Guangping,Zhang, Yiwen,Zhang, Yujie,Zhou, Wenxi
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p. 483 - 496
(2020/03/03)
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- N-alkylated linear heptamethine polyenes as potent non-azole leads against Candida albicans fungal infections
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In this study, eighteen heptamethine dyes were synthesised and their antifungal activities were evaluated against three clinically relevant yeast species. The eighteen dyes were placed within classes based on their core subunit i.e. 2,3,3-trimethylindolenine (5a-f), 1,1,2-trimethyl-1H-benzo[e]indole (6a-f), or 2-methylbenzothiazole (7a-f). The results presented herein imply that the three families of cyanine dyes, in particular compounds 5a-f, show high potential as selective scaffolds to treat C. albicans infections. This opens up the opportunity for further optimisation and investigation of this class compounds for potential antifungal treatment.
- Critchley, Megan E.,Lawrence, Clare L.,McKenna, Sean T.,Okoh, Adeyi Okoh,Smith, Robert B.,Vishwapathi, Vinod
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supporting information
(2020/07/21)
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- A near-infrared cyanine dye preparation method (by machine translation)
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The invention discloses a having excellent light stability of the near-infrared cyanine dye preparation method and use, the dye of the formula I as shown in the structural formula, R1 Hydrogen, methyl, in any one of a carboxyl group; R2 Hydrogen, methyl, alkoxy in any one of; X- Is iodine ion, bromide ion in any one of; n=1 - 5 is any integer. The dye through chemical bonding will be blocked piperidine structure unit introduced into the cycloheptane boeki indole cyanine in the mother's body, such that the resulting dye has good light stability, in the near-infrared region with absorption and emission, and has good photosensitive, photo-thermal characteristic, so that the fabric is colored, near-infrared fluorescence imaging, the photodynamic treatment, heat treating the field have good application prospect. (by machine translation)
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Paragraph 0076; 0081; 0082; 0083
(2019/01/14)
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- Tumour target probe compound, and synthesis and applications thereof
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The invention discloses a tumour target probe compound, and a preparation method, and applications thereof. The tumour target probe compound is represented by formula I, wherein R1 and R2 are used forrepresenting the same or different groups independently selected from C1-6 straight chain alkyl, C1-6 straight chain alkyl carboxyl, sulfonic acid group, or C1-6 straight chain alkyl ester groups, and X is used for representing halogen. It is confirmed by animal in vivo experiments that the tumour target probe compound possesses excellent tumour targeting effect, is capable of emitting fluorescence steadily and continuously, and can be used in tumour focus early stage diagnosis.
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Paragraph 0032; 0034; 0038; 0058; 0078; 0093; 0096; 0097
(2018/07/30)
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- Probe for early diagnosis of tumor as well as synthesis and application of probe
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The invention discloses an NQO (quinone oxidoreductase) response type near infrared fluorescence probe compound related to early diagnosis of tumor. The structure of the compound is represented as theformula (I), wherein R1 and R2 are the same or different, and R1 and R2 are independently selected from C1-6 linear alkyl, C1-6 linear alkyl carboxyl, sulfonyl or C1-6 linear alkyl ester; X is halogen. The primary cell confocal experiment of the compound proves that the compound has good NQO response capacity, can produce strong fluorescence easy to detect, and can be applied to early detection of tumor.
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Paragraph 0033; 0035; 0037; 0042; 0047; 0052
(2018/09/12)
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- Red-Fluorescent activatable probes for the detection of hydrogen peroxide in living cells
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Many inflammatory processes are associated with an increase in the production of reactive oxygen species (ROS). Chemical probes that specifically detect ROS are potentially useful tools for the early diagnosis of inflammatory diseases as well as cancer. Herein we have developed a library of coumarin hybrids by condensation of various heterocyclic quaternary salts to a 7-hydroxycoumarin scaffold. From our library we identified one benzothiazole-coumarin hybrid as a red-fluorescent compound with emission maxima around 620 nm and a strong fluorogenic response. Furthermore, we proved that this scaffold is suitable for the preparation of activatable probes, such as by modification with a boronate group for selective sensing of hydrogen peroxide (H2 O2 ). In vitro assays confirmed the reactivity and subsequent emission of our probe upon incubation with H2 O2 with good selectivity over different ROS and reactive nitrogen species (RNS) as well as minimal toxicity in cells. Finally cell imaging experiments were performed in murine macrophages and validated the utility of the activatable probe for the detection of H2 O2 in living cells.
- Garcia-Guzman, Claudia,Fernandez, Antonio,Avlonitis, Nicolaos,Bradley, Mark,Vendrell, Marc
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p. 353 - 361
(2016/07/06)
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- Cyanine dye for laveling biomolecule and preparation method thereof
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The present invention relates to a cyanine dye represented by [Chemical Formula 1] for labeling a biomolecule and a method for producing the same. [Chemical Formula 1] In [Chemical Formula 1], each of Y, Z, R_1, R_1andprime;, R_2, R_2andprime;, R_3, l and m is the same as defined in the specification.(AA) MarkerCOPYRIGHT KIPO 2015
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Paragraph 0231-0234
(2016/12/22)
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- A microwave-assisted and environmentally benign approach to the synthesis of near-infrared fluorescent pentamethine cyanine dyes
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A time-efficient and eco-conscious microwave methodology was developed and applied to synthesize a systematic library of pentamethine cyanine dyes and their corresponding precursors. The synthesis outlined herein drastically reduced the reaction pathway for pentamethine carbocyanine dye syntheses from days to min, as well as producing increased yields (89-98%) to the conventional heating method (18-64%). Twelve examples of pentamethine cyanine dyes were synthesized by means of microwave-assisted organic synthesis which provided excellent yield in expedited reaction time and were obtained using facile isolation methods. Furthermore, three cyanines were prepared with a novel methylene dioxy heterocyclic structure which imparted an approximately 40 nm bathochromic shift compared to unsubstituted counterparts; these results were shown to be in agreement with DFT calculations and HOMO-LUMO energy differences.
- Owens, Eric A.,Bruschi, Nicholas,Tawney, Joseph G.,Henary, Maged
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- A microwave-assisted and environmentally benign approach to the synthesis of near-infrared fluorescent pentamethine cyanine dyes
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A time-efficient and eco-conscious microwave methodology was developed and applied to synthesize a systematic library of pentamethine cyanine dyes and their corresponding precursors. The synthesis outlined herein drastically reduced the reaction pathway for pentamethine carbocyanine dye syntheses from days to min, as well as producing increased yields (89-98%) to the conventional heating method (18-64%). Twelve examples of pentamethine cyanine dyes were synthesized by means of microwave-assisted organic synthesis which provided excellent yield in expedited reaction time and were obtained using facile isolation methods. Furthermore, three cyanines were prepared with a novel methylene dioxy heterocyclic structure which imparted an approximately 40 nm bathochromic shift compared to unsubstituted counterparts; these results were shown to be in agreement with DFT calculations and HOMO-LUMO energy differences.
- Owens, Eric A.,Bruschi, Nicholas,Tawney, Joseph G.,Henary, Maged
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- A macrophage uptaking near-infrared chemical probe CDnir7 for in vivo imaging of inflammation
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Visualization of macrophages in live animals has been of great interest for a better understanding of inflammation. We developed a near infrared (NIR) probe CDnir7 that can selectively detect macrophages and visualize inflammation in vivo using the IVIS spectrum, Fluorescence Molecular Tomography (FMT) and Multi-Spectral Optoacoustic Tomography (MSOT). This journal is the Partner Organisations 2014.
- Kang, Nam-Young,Park, Sung-Jin,Ang, Xiao Wei Emmiline,Samanta, Animesh,Driessen, Wouter H. P.,Ntziachristos, Vasilis,Vasquez, Kristine O.,Peterson, Jeffrey D.,Yun, Seong-Wook,Chang, Young-Tae
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supporting information
p. 6589 - 6591
(2014/06/10)
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- N-Alkylated 2,3,3-trimethylindolenines and 2-methylbenzothiazoles. Potential lead compounds in the fight against Saccharomyces cerevisiae infections Dedication in memory of the late Derek Bennett 17-07-1931 to 05-04-2013.
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The synthesis of a variety of N-alkylated 2,3,3-trimethylindolenines and 2-methylbenzothiazoles is reported herein. Their potential as antifungal agents is evaluated by preliminary screening against Saccharomyces cerevisiae (S. cerevisiae), Schizosaccharomyces pombe (S. pombe), and Candida albicans (C. albicans). Statistical analyses illustrate a strong relationship between chain length and growth inhibition for S. cerevisiae and S. pombe (p 0.0001 in every case). Of particular interest is the activity of both sets of compounds against S. cerevisiae, as this is emerging as an opportunistic pathogen, especially in immunosuppressed and immunocompromised patients. Bioassays were set up to compare the efficacy of our range of N-alkylated compounds against classic antifungal agents; Amphotericin B and Thiabendazole.
- Tyler, Andrew R.,Okoh, Adeyi Okoh,Lawrence, Clare L.,Jones, Vicky C.,Moffatt, Colin,Smith, Robert B.
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supporting information
p. 222 - 227
(2013/07/27)
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- PROCESS FOR DYE PRODUCTION
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The present invention relates to a process for the production of certain compounds, especially dye compounds defined in general by Formula I: The invention provides a one-step method in which a compound of Formula II or a reactive intermediate derived in situ therefrom is reacted in situ with a compound of Formula III (optionally in the presence of a compound of Formula IV) to produce compounds of Formula I in excellent yield, and in a manner which avoids undesirable by- product formation.
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Paragraph 00121
(2013/08/15)
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- Design strategy for a near-infrared fluorescence probe for matrix metalloproteinase utilizing highly cell permeable boron dipyrromethene
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Near-infrared (NIR) fluorescence probes are especially useful for simple and noninvasive in vivo imaging inside the body because of low autofluorescence and high tissue transparency in the NIR region compared with other wavelength regions. However, existi
- Myochin, Takuya,Hanaoka, Kenjiro,Komatsu, Toru,Terai, Takuya,Nagano, Tetsuo
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supporting information; experimental part
p. 13730 - 13737
(2012/10/08)
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- Solid-state fluorescence of squarylium dyes
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An N-butyl indolenine squarylium dye could include toluene and p-xylene and exhibited the solid-state fluorescence in near-infrared region (F max=761 nm) in crystalline form due to inhibition of π/π-interactions between the fluorophores.
- Matsui, Masaki,Fukushima, Masato,Kubota, Yasuhiro,Funabiki, Kazumasa,Shiro, Motoo
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scheme or table
p. 1931 - 1935
(2012/04/10)
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- Ultrasensitive near-infrared Raman reporters for SERS-based in vivo cancer detection
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Of good report: Synthesis and screening of an 80-member tricarbocyanine library identified CyNAMLA-381 as a near-IR surface-enhanced Raman spectroscopy (SERS) reporter with good signal stability and higher sensitivity than the standard. Encapsulation of CyNAMLA-381 on gold nanoparticles and conjugation to an antibody afforded SERS nanotags with excellent sensitivity, stability, and tumor specificity in xenograft models (see picture). Copyright
- Samanta, Animesh,Maiti, Kaustabh Kumar,Soh, Kiat-Seng,Liao, Xiaojun,Vendrell, Marc,Dinish,Yun, Seong-Wook,Bhuvaneswari, Ramaswamy,Kim, Hyori,Rautela, Shashi,Chung, Junho,Olivo, Malini,Chang, Young-Tae
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supporting information; experimental part
p. 6089 - 6092
(2011/08/05)
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- DEVELOPMENT OF PHOTOSTABLE NEAR-IR CYANINE DYES FOR IN VIVO IMAGING
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A compound of structural formula (I). The values and alternative values are as defined herein. The invention also includes biosensors comprising nanoparticles functionalized with a compound of structural formula (I). Also described is a method for labeling a biomolecule using a compound of structural formula (I) and a method of detecting a target biomolecule using a compound of structural formula (I) or a biosensor of the invention.
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Page/Page column 44
(2011/10/13)
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- Development of photostable near-infrared cyanine dyes
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With the emerging interest in optical in vivo imaging, there is an increasing demand of photostable near-infrared (NIR) dyes. Herein we report the rational design of an amine tricarbocyanine structure with improved photostability (CyNA) and its combinatorial derivatization to render CyNA-414 as a NIR-fluorescent dye with stronger emission intensity and higher photostability than the NIR standard IndoCyanine Green (ICG).
- Samanta, Animesh,Vendrell, Marc,Das, Rajkumar,Chang, Young-Tae
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supporting information; experimental part
p. 7406 - 7408
(2010/11/18)
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- Synthesis and characterization of heptamethine NIR absorbing cyanine dye compounds
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In this work, new heptamethine near infrared (NIR) absorbing cyanine dye compounds were designed and synthesized by the reaction of bis-aldehyde, (1-formyl-3-hydroxymethylene)cyclohexene with benzindole derivatives. These dyes contained different Nalkyl c
- Shin, Joung-Il,Park, Soo-Youl,Shin, Seung-Rim,Jun, Kun,Youn, Hye-Soo,An, Kyoung-Lyong,Son, Young-A
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experimental part
p. 621 - 625
(2011/10/30)
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