- Croconaine rotaxane for acid activated photothermal heating and ratiometric photoacoustic imaging of acidic pH
-
Absorption of 808 nm laser light by liposomes containing a pH sensitive, near-infrared croconaine rotaxane dye increases dramatically in weak acid. A stealth liposome composition permits acid activated, photothermal heating and also acts as an effective nanoparticle probe for ratiometric photoacoustic imaging of acidic pH in deep sample locations, including a living mouse.
- Guha, Samit,Shaw, Gillian Karen,Mitcham, Trevor M.,Bouchard, Richard R.,Smith, Bradley D.
-
-
Read Online
- Synthesis, characterization, and UV–visible study of some new photochromic formyl-containing 1′,3′,3′-trimethylspiro[chromene-2,2′-indoline] derivatives
-
The spiropyran derivatives can exist in two forms, the closed-ring spiropyran form and the open-ring merocyanine (MC) form. The SP form could be converted into the MC form upon UV irradiation. In this work, some 1′,3′,3′-trimethylspiro[chromene-2,2′-indoline] derivatives containing the nitro and formyl groups are synthesized via the reaction of 1,3,3-trimethyl-2-methylene-5-nitroindoline with the corresponding salicylaldehyde derivatives. These compounds have different photochromic behaviors. The synthesized photochromic molecules are characterized by the FT-IR, 1H-NMR, and 13C-NMR spectroscopic techniques. In order to investigate the photochromic properties of these compounds, the UV–visible spectroscopic analyses of their methanolic solutions before and after exposure to a UV lamp (in the spectral range of 360–400?nm) are studied. Graphic abstract: [Figure not available: see fulltext.].
- Sepehr, Zeinalabedin,Nasr-Isfahani, Hossein,Mahdavian, Ali Reza,Amin, Amir Hossein
-
p. 3061 - 3067
(2021/05/27)
-
- Heptamethine nitroindole cyanine dye, preparation method and application thereof
-
The invention discloses a heptamethine nitro indocyanine dye, a preparation method and application thereof, and belongs to the field of polymethine indocyanine dyes and preparation thereof, wherein the structural formula of the heptamethine nitro indocyanine dye is represented by a formula (I). The preparation method comprises the following steps: 1) carrying out a heating reaction on raw materials containing a 2,3,3-trimethyl-nitroindole derivative and a nucleophilic substituted compound under a vacuum condition to obtain an organic ammonium salt; and 2) carrying out a heating reaction on a solution containing the organic ammonium salt obtained in the step 1) and a cycloalkene derivative under a closed condition. The dye has near-infrared light absorption and fluorescence development properties, and can be used as a probe auxiliary agent; and the preparation method has the advantages of short synthesis route, environment-friendly solvent, simple process, avoidance of noble metal catalysis, high yield, high purity and the like, is high in applicability, and can be used for synthesizing products of various structure types.
- -
-
Paragraph 0155-0156
(2020/09/23)
-
- PH reversible activation type photo-thermal/photodynamic/fluorescent integrated probe molecule
-
The invention discloses a pH reversible activation type photo-thermal/photodynamic/fluorescent integrated probe molecule, and belongs to the technical field of biological medicines. A pH-responsive asymmetric cyanine structure is used as a core unit, and through structural modification and introduction of halogen and other heavy atoms into a conjugated system, a photo-thermal/photodynamic/fluorescent integrated probe molecule capable of being specifically activated by a tumor weakly acidic microenvironment is constructed. The photo-thermal/photodynamic/fluorescent integrated probe has good stability, a good photo-thermal effect and excellent active oxygen generation capacity, and has huge potential in tumor treatment.
- -
-
Paragraph 0054-0058; 0059
(2020/09/08)
-
- Effects of Substituents on Metastable-State Photoacids: Design, Synthesis, and Evaluation of their Photochemical Properties
-
Recently, metastable-state photoacids have been widely used to control proton transfer in numerous chemical and biological processes as well as applications with visible light. Generally, substituents have a great influence on the photochemical properties of molecules, which will further affect their applications. Yet, the effects of substituents on metastable-state photoacids have not been studied systematically. In this work, 16 metastable-state photoacid derivatives were designed and synthesized on the basis of substituents having a large range of σ–π electron–donor–acceptor capabilities. The effects of substituents on the color display [or maximum absorption band(s)], solubility, pKa values, dark/photoacidity, photosensitivity, and relaxation kinetic(s) were investigated in detail. This study will be helpful for the targeted design and synthesis of promising photoacids and the application of their photocontrolled proton-release processes in functional materials/devices.
- Liu, Junning,Tang, Wenqi,Sheng, Lan,Du, Zhen,Zhang, Ting,Su, Xing,Zhang, Sean Xiao-An
-
supporting information
p. 438 - 445
(2019/01/08)
-
- A highly sensitive fluorescent probe that quantifies transthyretin in human plasma as an early diagnostic tool of Alzheimer's disease
-
The development of sensitive and reliable fluorescent probes for the early diagnosis of Alzheimer's disease (AD) is highly challenging and plays an important role in achieving effective treatments. Herein, we designed and synthesized an indole-based fluorophore for TTR in human plasma, an important hallmark of AD pathogenesis. This robust and simple fluorescent method allows quantification of TTR in the complex biological matrix.
- Lim, Hye Rim,Kim, Seo Yun,Jeon, Eun Hee,Kim, Yun Lan,Shin, Yu Mi,Koo, Tae-Sung,Park, Sung Jean,Hong, Ki Bum,Choi, Sungwook
-
supporting information
p. 10424 - 10427
(2019/09/07)
-
- Analysis of Bisulfite Via a Nitro Derivative of Cyanine-3 (NCy3) in the Microfluidic Channel
-
NCy3, a derivative of Cyanine 3 with a nitro substituent, showed a high reactivity to bisulfite in aqueous media, instantly leading to ratiometric change of absorption spectra and significant fluorescence quenching. Applied in the microfluidic channel, NCy3 functionalize as a sensitive approach for quantitative detection of bisulfite, particularly for samples with a small volume.
- Houtwed, Haley A.,Xie, Meng,Ahmad, Aatiya,Masters, Cody D.,Davison, Melissa M.,Kounovsky-Shafer, Kristy,Cao, Haishi
-
p. 523 - 529
(2019/06/11)
-
- Photooxidation of oxazolidine molecular switches: Uncovering an intramolecular ionization facilitated cyclization process
-
Photooxidation of oxazoline (OXA) molecular switches through media-induced intramolecular ionization is reported. The formation of the photooxidation product occurs by attack of the flexible donor group (-CH2CH2OH) to the adjacent CC with 1O2 as the oxidant. The novel seven-membered ring sub-structure of the photooxidation product was inferred by HRMS, IR and 1H NMR spectroscopy. Additionally, acid released from solvent photolysis was found to affect the product formation and efficiency of the photooxidation.
- Chen, Qiaonan,Sheng, Lan,Du, Jiahui,Xi, Guan,Zhang, Sean Xiao-An
-
supporting information
p. 5094 - 5097
(2018/05/26)
-
- Two near-infrared highly sensitive cyanine fluorescent probes for pH monitoring
-
Two near-infrared (NIR) pH-activated heptamethine indocyanine probes with quaternary ammonium unit were designed and synthesized. The absorption and emission titrations indicate that cationic structure improves the cyanine dye's aqueous solubility and these two probes exhibit highly sensitive response to pH in acid condition. Their fluorescence intensities both gradually increase about 25-fold from pH 7.60 to 3.00 with pKa values of 4.72 and 4.45 respectively, which are suitable for studying acidic organelles in living cells. Moreover, their fluorescence intensities are linearly proportional to pH values in the range of 5.50–4.00. These results are probably attributed to the protonation of the indole nitrogen atoms, which are verified by 1H NMR spectra. Furthermore, these two probes can achieve real-time imaging of cellular pH and detection of pH in situ in living HeLa cells due to their excellent properties, including good reversibility, desirable photostability, high selectivity, low cytotoxicity and remarkable membrane permeability.
- Hou, Jing-Ru,Jin, Di,Chen, Bo,Si, Lei-Lei,Jin, Yue-Hua,Chen, Li-Gong,Yan, Xi-Long,Wang, Bo-Wei,Li, Yang
-
p. 1681 - 1687
(2017/07/27)
-
- Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines
-
Spiropyrans and spirooxazines represent an important class of photochromic compounds with a wide variety of applications. In order to effectively utilize and design these photoswitches it is desirable to understand how the substituents affect photochromic properties, and how the different structural motifs compare under identical conditions. In this work a small library of photoswitches was synthesized in order to comparatively evaluate the effect of substituent modifications and structure on photochromism. The library was designed to modify positions that were believed to have the greatest effect on C-O bond lability and therefore the photochromic properties. Herein we report a comparative analysis of the UV and visible light responses of 30 spiropyrans, spiroindolinonaphthopyrans, and spirooxazines. The influence of gadolinium(III) binding was also investigated on the library of compounds to determine its effect on photoswitching. Both assays demonstrated different trends in substituent and structural requirements for optimal photochromism.
- Balmond, Edward I.,Tautges, Brandon K.,Faulkner, Andrea L.,Or, Victor W.,Hodur, Blanka M.,Shaw, Jared T.,Louie, Angelique Y.
-
p. 8744 - 8758
(2016/10/14)
-
- Efficient Synthesis of Chiral Indolines using an Imine Reductase from Paenibacillus lactis
-
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
-
supporting information
p. 1692 - 1696
(2015/06/02)
-
- LABELS, THEIR PRODUCTION PROCESS AND THEIR USES
-
Labels are disclosed capable of forming a covalent or non-covalent bond with a target molecule, particularly a biological molecule. The structure of these labels may consist of a dye covalently bound by one or more carbons on its chemical structure to one or more [FUNC] group(s), and optionally one or more [SOL] group(s). The structure of these labels allow selection of dyes from a wide variety of different excitation and emission wavelengths and allow easy functionalization of the dye without appreciably altering its spectral characteristics or its solubility characteristics.
- -
-
Page/Page column 14; 18
(2012/03/10)
-
- New 3H-indole synthesis by fischer's method. Part I.
-
Methyl indolenines (4a-c) and (5a-c) were prepared in high yield by a Fischer indole synthesis reaction of o,m-tolylhydrazine hydrochlorides (1a-b) with isopropyl methyl ketone (2) and 2-methylcyclohexanone (3) in acetic acid at room temperature. o,pNitrophenylhydrazines (1c-d) were reacted with 2-methylcyclohexanone (3) in acetic acid at reflux to give nitroindolenines (5d-e), while the attempted reactions of o,pnitrohydrazines with isopropyl methyl ketone (2) in acetic acid were not successful. Compounds (1c-d) were reacted with isopropyl methyl ketone (2) in acetic acid/HCl to give 2,3,3-trimethyl-5-nitro-indolenine (4e) and 2,3,3-trimethyl-7-nitroindolenine (4d). Copyright
- Sajjadifar, Sami,Vahedi, Hooshang,Massoudi, Abdolhossien,Louie, Omid
-
scheme or table
p. 2491 - 2498
(2010/07/10)
-
- Two-way molecular switches with large nonlinear optical contrast
-
To optimize the nonlinear optical (NLO) contrast, a series of indolinooxazolidine derivatives with electron-withdrawing substituents in the para position on the indolinic residue have been synthesized. Their linear and nonlinear optical properties have been characterized by UV-visible absorption and hyper-Rayleigh scattering measurements, as well as by ab initio calculations. The two-way photo- or pH-triggered switching mechanism has been demonstrated by comparing the absorption spectra of the zwitterionic and protonated open forms (POF). Hyper-Rayleigh measurements have revealed that the second-order NLO contrast between the closed indolinooxazolidine and the open it-conjugated colored forms remain very large upon substitution. Theory and measurements show that for the POFs the amplitude of the first hyperpolarizability follows the Hammett parameters of the withdrawing groups. However, because the measurements are performed in resonance, to recover this behavior, elaborate procedures including homogeneous and inhomogeneous broadenings, as well as single-mode vibronic structures are necessary to extrapolate to the static limit.
- Mancois, Fabien,Pozzo, Jean-Luc,Pan, Jianfeng,Adamietz, Frederic,Rodriguez, Vincent,Ducasse, Laurent,Castet, Frederic,Plaquet, Aurelie,Champagne, Benoit
-
experimental part
p. 2560 - 2571
(2009/12/03)
-
- Synthesis of some new substituted photochromic N,N′-bis(spiro[1- benzopyran-2,2′-indolyl])diazacrown systems with substituent control over ion chelation
-
The reversible photochemical ion chelation of the newly synthesised substituted N,N′-bis(spiro[1-benzopyran-2,2′-indolyl])diazacrown systems 15a-c and the subsequent molecular electronic control of this process using appropriately placed substituent groups on the spiro-benzopyran skeleton is reported. The principle of molecular electronic control of ion chelation is demonstrated by comparing the behaviour of the newly synthesised nitro-substituted and pyrido-annulated spiro-benzopyran system 9b with that of the unsubstituted compound 9a. Electronic substituent control over ion chelation is then exemplified for the new N,N′-bis(5′-nitrospiro[1- benzopyran-2,2′-indolyl])diazacrown system 15c and further exemplified for the corresponding 5′-trifluoromethyl derivative 15b, which contains the photochemically more robust trifluoromethyl group. The crown system 15a, unsubstituted in the spiro-indole moiety, is also reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Roxburgh, Craig J.,Sammes, Peter G.
-
p. 1050 - 1056
(2007/10/03)
-
- Synthesis and structure of indoline spiropyrans of the coumarin series
-
New indoline spiropyrans of the coumarin series were synthesized by the condensation of indoline and hydroxyformylcoumarin derivatives. Spiropyrans, viz., derivatives of 8-formyl-7-hydroxy-4-methylcoumarin and 5-formyl-6-hydroxy-4-methylcoumarin, under irradiation are transformed into open forms, which are recyclized in the dark. The compounds formed by the condensation of the indoline derivatives with 3-formyl-4-hydroxycoumarin have an open structure of the merocyanine dyes and are transformed into spiro forms neither in the dark nor under irradiation with the visible light.
- Traven,Miroshnikov,Chibisova,Barachevsky,Venidiktova,Strokach
-
p. 2417 - 2424
(2007/10/03)
-
- ENERGY TRANSFER ASSAY METHOD AND REAGENT
-
Disclosed is a non-fluorescent cyanine dye that may be used as an acceptor in fluorescence energy transfer assays involving the detection of binding and/or cleavage events in reactions involving biological molecules, and assay methods utilising such dyes. The non-fluorescent cyanine dye is a compound of formula (I), wherein the linker group Q contains at least one double bond and forms a conjugated system with the rings containing X and Y; groups R, R, Rand Rare attached to the rings containing X and Y, or optionally, are attached to atoms of the Zand Zring structures; Zand Zeach represent a bond or the atoms necessary to complete one or two fused aromatic rings each ring having five or six atoms, selected from carbon atoms and, optionally, no more than two oxygen, nitrogen and sulphur atoms; at least one of groups R, R, R, R, R, Rand Ris a target bonding group; any remaining groups R, R, R, Rand Rgroups are independently selected from the group consisting of hydrogen, C1-C4 alkyl, OR, COOR, nitro, amino, acylamino, quaternary ammonium, phosphate sulphonate and sulphate, where Ris selected from H and C1-C4 alkyl; any remaining Rand Rare selected from C1-C10 alkyl which may be unsubstituted or substituted with phenyl, the phenyl being optionally substituted by up to two substituents selected from carboxyl, sulphonate and nitro groups; characterised in that at least one of the groups R, R, R, R, R, Rand Rcomprises a substituent which reduces the fluorescence emission of said dye such that it is essentially non-fluorescent.
- -
-
-
- Cyanine Borate Salts That Form Penetrated Ion Pairs in Benzene Solution: Synthesis, Properties, and Structure
-
A series of cyanine borate salts were prepared and studied by laser spectroscopy, fluorescence spectroscopy, NMR spectral methods, and computer modeling.Analysis of the chemical, physical, and spectral properties of these salts shows that, in benzene solution, they form penetrated ion pairs.The center-to-center distance between the ions is less than the sum of the individual ionic radii.We call such structures penetrated ion pairs.Penetration affects the properties of the cyanine dyes in unique ways that are described.
- Murphy, Sean,Yang, Xiquiang,Schuster, Gary B.
-
p. 2411 - 2422
(2007/10/02)
-
- SYNTHESE DE QUELQUES SPIRO ET SPIRO PHOTOCHROMIQUES. APPLICATION DE LA METHODOLOGIE DE LA RECHERCHE EXPERIMENTALE
-
Some spiro I and spiro II substituted by different groups were synthesized in order to evaluate their photochromic properties and to optimize the preparation of spiroheterocyclic systems.In addition, some spiro III were also prepared as reference compounds.Their physical and spectroscopic characteristics (UV, 1H and 13C) were determined.A study using the experimental design methodology allowed to point out the most important factors for improving the reaction yields. KEYWORDS: Photochromism, spirooxazines, spiropyrans, synthesis, 1H NMR, experimental design methodology.
- Pottier, E.,Sergent, M.,Luu, R. Phan Tan,Guglielmetti, R.
-
p. 719 - 740
(2007/10/02)
-
- THE STRUCTURE OF SOME HYDROXYALKYL DERIVATIVES OF 2-METHYLENE-3,3-DIMETHYLINDOLINE
-
2-Methylene-1-(ω-hydroxyalkyl)-3,3-dimethylindolines occur both in solution and in the solid state in the form of cyclic tautomers.By contrast 2-formylmethylene-1-(2-hydroxyethyl)-3,3-dimethylindoline is not susceptible to cyclization in solution or in the solid state.
- Bartnik, Romuald,Mloston, Grzegorz,Lesniak, Stanislaw
-
p. 1957 - 1961
(2007/10/02)
-
- PHOTOCHROMISM. SYNTHESIS AND PROPERTIES OF INDOLINOSPIROBENZOTHIOPYRANS
-
Novel photochromic compounds, indolinospirobenzothiopyrans, were prepared and their properties in polymer films were examined.The absorption bands of the colored form lie around 100 nm deeper in the long-wave region of the spectrum than are the case with the common spiropyrans.
- Arakawa, Sei'ichi,Kondo, Hirofumi,Seto, Jun'etsu
-
p. 1805 - 1808
(2007/10/02)
-
- Investigation of the Quasi-Liquid Crystal Structure
-
Quasi-lipid crystals, a metastable mesophase of thermochromic spiropyrans containing mesogenic groups, were investigated by different methods.Miscibility studies, X-ray diffraction, and UV-visible and FT-IR spectroscopy indicate that the material behaves basically as a nematic mesophase.Comparison of data of the present work with that obtained earlier by optical and ESR investigation of the behavior of fluorescent and paramagnetic probes results in the formulation of a structural model for quasi-liquid crystals.
- Shvartsman, Felix P.,Cabrera, Ivan R.,Weis, Alexander L.,Wachtel, Ellen J.,Krongauz, Valeri A.
-
p. 3941 - 3946
(2007/10/02)
-