- Supramolecular Dimerization and [2 + 2] Photocycloaddition Reactions of Crown Ether Styryl Dyes Containing a Tethered Ammonium Group: Structure-Property Relationships
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Molecular self-assembly is an effective strategy for controlling the [2 + 2] photocycloaddition reaction of olefins. The geometrical properties of supramolecular assemblies are proven to have a critical effect on the efficiency and selectivity of this photoreaction both in the solid state and in solution, but the role of other factors remains poorly understood. Convenient supramolecular systems to study the structure-property relationships are pseudocyclic dimers spontaneously formed by styryl dyes containing a crown ether moiety and a remote ammonium group. New dyes of this type were synthesized to investigate the effects of structural and electronic factors on the quantitative characteristics of supramolecular dimerization and [2 + 2] photocycloaddition in solution. Variable structural parameters for the styryl dyes were the size and structure of macrocyclic moiety, the nature of heteroaromatic residue, and the length of the ammonioalkyl group attached to this residue. Quantum chemical calculations of the pseudocyclic dimers were performed in order to interpret the relationships between the structure of the ammonium dyes and the efficiency of the supramolecular photoreaction. One of the dimeric complexes was obtained in the crystalline state and studied by X-ray diffraction. The results obtained demonstrate that the photocycloaddition in the pseudocyclic dimers can be dramatically affected by the electronic structure of the styryl moieties, as dependent on the electron-donating ability of the substituents on the benzene ring, and by the conformational flexibility of the pseudocycle, which determines the mobility of the olefinic bonds. The significance of electronic factors is highlighted by the fact that the photocycloaddition quantum yield in geometrically similar dimeric structures varies from ≤10-4 to 0.38. The latter value is unusually high for olefins in solution.
- Ushakov, Evgeny N.,Vedernikov, Artem I.,Lobova, Natalia A.,Dmitrieva, Svetlana N.,Kuz'Mina, Lyudmila G.,Moiseeva, Anna A.,Howard, Judith A.K.,Alfimov, Michael V.,Gromov, Sergey P.
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Read Online
- Nanoaggregate Probe for Breast Cancer Metastasis through Multispectral Optoacoustic Tomography and Aggregation-Induced NIR-I/II Fluorescence Imaging
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An activatable nanoprobe for imaging breast cancer metastases through near infrared-I (NIR-I)/NIR-II fluorescence imaging and multispectral optoacoustic tomography (MSOT) imaging was designed. With a dihydroxanthene moiety serving as the electron donor, quinolinium as the electron acceptor and nitrobenzyloxydiphenylamino as the recognition element, the probe can specifically respond to nitroreductase and transform into an activated D-π-A structure with a NIR emission band extending beyond 900 nm. The activated nanoprobe exhibits NIR emission enhanced by aggregation-induced emission (AIE) and produces strong optoacoustic signal. The nanoprobe was used to detect and image metastases from the orthotopic breast tumors to lymph nodes and then to lung in two breast cancer mouse models. Moreover, the nanoprobe can monitor the treatment efficacy during chemotherapeutic course through fluorescence and MSOT imaging.
- Ouyang, Juan,Sun, Lihe,Wu, Shuizhu,Zeng, Cheng,Zeng, Fang,Zeng, Zhuo
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Read Online
- A dual-analytes responsive fluorescent probe for discriminative detection of ClO? and N2H4 in living cells
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Hydrazine (N2H4) and ClO? are very harmful for public health, hence it is important and necessary to monitor them in living cells. Herein, we rationally designed and synthesized a dual-analytes responsive fluorescent sensor PTMQ for distinguishing detection of N2H4 and ClO?. PTMQ underwent N2H4-induced double bond cleavage, affording colorimetric and green fluorescence enhancement with good selectivity and a low detection limit (89 nM). On the other hand, PTMQ underwent ClO?-induced sulfur oxidation and displayed red fluorescence lighting-up response towards ClO? with good selectivity, rapid response (2H4 and ClO? in living cells.
- Bao, Guang-Ming,Hu, Xichao,Rodrigues, Jo?o,Sheng, Ruilong,Wu, Xiaoli,Zhu, Beitong
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Read Online
- Distinguishing normal and inflammatory models by viscosity changes with sensitively mitochondrial-trackable fluorescent probe
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Biological microenvironment plays a momentous role in the regulation of various vital activities, and its abnormal changes are often closely related to some diseases. Viscosity, as an indispensable part of microenvironment parameters, has always been one
- Geng, Chen,Hao, Xinya,Lin, Weiying,Song, Wenhui,Zhan, Jingting
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supporting information
(2021/08/19)
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- Ratio type viscosity fluorescent probe and preparation method and application thereof
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The invention discloses a ratio type viscosity fluorescent probe which has the following structural formula: the ratio type viscosity fluorescent probe can reduce interference of background and impurities, and has good sensitivity during viscosity detection; the cell viscosity detection reagent is simple, rapid and sensitive, has low toxicity to cells, and the probe has a wide application prospect in the field of biomolecule detection. The invention also provides a preparation method and application of the ratio type viscosity fluorescent probe. The ratio type viscosity fluorescent probe can be used for viscosity determination in a solution system or a biological system.
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Paragraph 0047; 0056-0059
(2021/06/09)
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- Quinoline hydrogen peroxide fluorescent probe and preparation method thereof
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The invention provides a quinoline hydrogen peroxide fluorescent probe and a preparation method thereof, and belongs to the field of organic dye synthesis. The quinoline hydrogen peroxide probe prepared by the method is a black solid in appearance, and th
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Paragraph 0034-0036; 0048-0050; 0055-0057; 0062-0064
(2020/10/04)
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- Synthesis and antileishmanial evaluation of thiazole orange analogs
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Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.
- Abdelhameed, Ahmed,Liao, Xiaoping,McElroy, Craig A.,Joice, April C.,Rakotondraibe, Liva,Li, Junan,Slebodnick, Carla,Guo, Pu,Wilson, W. David,Werbovetz, Karl A.
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supporting information
(2019/11/28)
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- Preparation method of quinoline heptamethine cyanine dye
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The invention relates to near infrared quinoline type heptamethine cyanine dye and a preparation method thereof and belongs to the field of chemical organic dye synthesis. Synthetic near infrared dyehas the advantages of excellent optical performance such as in a near infrared region 2, large compound Stokes shift, high photostability, few synthesis step and convenience for purification. The mostobvious characteristics of the dye include high absorptivity in the near infrared zone 2, excellent penetrability to environment and biological tissue and high quantum yield in an organic solvent like dichloromethane. The dye can be used in the field of biomolecular marking and fluorescence imaging. A probe preparation method is simple and easy to implement, low in cost, good in economic benefitand suitable for industrial production.
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Paragraph 0002
(2018/09/11)
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- A Far-Red Fluorescent DNA Binder for Interaction Studies of Live Multidrug-Resistant Pathogens and Host Cells
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Transgene expression of green fluorescent protein (GFP) has facilitated the spatiotemporal investigation of host–pathogen interactions; however, introduction of the GFP gene remains challenging in drug-resistant bacteria. Herein, we report a novel far-red fluorescent nucleic acid stain, 6-TramTO-3, which efficiently labels bacteria through a DNA binding mode without affecting growth and viability. Exemplarily, we stained Klebsiella pneumoniae, a major threat to hospitalized patients, and deciphered divergent interaction strategies of antibiotic-resistant and antibiotic-sensitive Klebsiella strains with immune cells. 6-TramTO-3 constitutes an off-the-shelf reagent for real-time analysis of bacterial infection, including strains for which the use of genetically encoded reporters is not feasible. Eventually, our approach may aid the development of strategies to combat a major worldwide health threat: multidrug-resistant bacteria.
- Schulte, Leon N.,Heinrich, Benedikt,Janga, Harshavardhan,Schmeck, Bernd T.,Vázquez, Olalla
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supporting information
p. 11564 - 11568
(2018/09/10)
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- A study on the AMACR catalysed elimination reaction and its application to inhibitor testing
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α-Methylacyl-CoA racemase (AMACR; P504S) catalyses a key step in the degradation of branched-chain fatty acids and is important for the pharmacological activation of Ibuprofen and related drugs. Levels of AMACR are increased in prostate and other cancers,
- Yevglevskis, Maksims,Lee, Guat L.,Sun, Jenny,Zhou, Shiyi,Sun, Xiaolong,Kociok-K?hn, Gabriele,James, Tony D.,Woodman, Timothy J.,Lloyd, Matthew D.
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p. 612 - 622
(2016/01/12)
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- The fluorescent dye, synthesis method and use thereof (by machine translation)
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The present invention provides a category of cyanine dyes having the following general structural Formula I, wherein X is defined as C(CH3)2, O, S or Se; m is an integer from 1 to 18, R1 and R2 are each independently chosen from H, C1-18alkyl, OR7, C1-6alkyl-OR7 or halogen; R3 is pyrrolyl, imidazolyl, piperidinyl, piperazinyl, morpholinyl, guanidino, NHR5 or N(R6)2; R4 is C1-18alkyl, benzyl or (CH2)mR3; R5 is saturated and/or unsaturated, straight-chained and/or branched-chained C1-18alkyl, hydroxy alkyl, mercapto-alkyl, amino alkyl, acyl, phenyl, naphthyl or benzyl; R6 is a C2-18alkyl; R7 is H or a C1-18alkyl; Y? is an anion. The mentioned compounds can be applied to staining biological samples, to the fields of nucleic acids labeling, blood cell analysis, clinical diagnosis, immunological assays and etc.
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Paragraph 0077
(2016/10/09)
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- The third-order nonlinear optical properties of charge flowable trimethine cyanine with quinolone groups
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Organic molecules with charge flow abilities gain much attention in third-order nonlinear optical materials. To evaluate the hypothesis of terminal donor and/or acceptor groups participating organic resonance structures for third-order nonlinear optical materials, conjugated double bonds structures with terminal amino groups are selected in this paper. The trimethine cyanine dye with quinolone skeleton (3a) was synthesized, it shows strong reverse saturable absorption and nonlinear refraction in dimethyl formamide solution at 532 nm. Then, its derivative compound (3b) with long alkyl chains was synthesized in order to improve the film forming performance, the spinning coating thin film exhibits strong reverse saturable absorption with the third-order nonlinear susceptibilities χI(3)=3.42×10-8esu and χ( 3)=3.23×10-9esu under nanosecond and picosecond laser beams respectively. The results validate that the organic compounds with terminal donor and/or acceptor groups participating resonance structures have potential value for the design of the third-order nonlinear optical materials.
- Miao, Jia-Tao,Wu, Xing-Zhi,Sun, Ru,Song, Ying-Lin,Ge, Jian-Feng
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- Synthesis of quaternary heterocyclic salts
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The microwave synthesis of twenty quaternary ammonium salts is described. The syntheses feature comparable yields to conventional synthetic methods reported in the current literature with reduced reaction times and the absence of solvent or minimal solvent.
- Winstead, Angela J.,Nyambura, Grace,Matthews, Rachael,Toney, Deveine,Oyaghire, Stanley
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p. 14306 - 14319
(2014/01/06)
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- An effective minor groove binder as a red fluorescent marker for live-cell DNA imaging and quantification
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Seeing red: DEAB-TO-3 shows a large fluorescence enhancement upon binding to native DNA and a distinct selectivity for double-stranded DNA over total RNA. As a red fluorescent live-cell-permeant DNA minor groove binder, DEAB-TO-3 is promising for highly sensitive DNA detection in vitro and nucleus-specific imaging and DNA quantification in vivo (see picture). Copyright
- Peng, Xiaojun,Wu, Tong,Fan, Jiangli,Wang, Jingyun,Zhang, Si,Song, Fengling,Sun, Shiguo
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supporting information; experimental part
p. 4180 - 4183
(2011/07/07)
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- Delocalized cationic azo dyes containing a thiazole moiety
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Several new delocalized cationic azo dyes incorporating a bathochromic thiazole moiety have been prepared in moderate to good yields. The synthesis involved the Knoevenagel condensation of an intermediate azo compound, bearing a terminal formyl group, with methylenic bases generated in situ from benzoazolium and quinolinium salts. All dyes display strong absorption around 700 nm and have shown negative solvatochromic behaviour.
- Salvador, Maria A.,Reis, Lucinda V.,Almeida, Paulo,Santos, Paulo F.
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p. 299 - 303
(2008/09/16)
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- Dyeing method using a specific cationic derivative and a compound selected among a specific aldehyde, a specific ketone, a quinone and a di-imino-isoindoline or 3-amino-isoindolone derivative
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Compositions, methods, and kits for dyeing at least one keratin fiber, comprising at least one specific cationic compound and at least one compound chosen from specific aldehydes, specific ketones, quinones, diiminoisoindoline derivatives, and 3-aminoisoindolone derivatives, with the proviso that the inventive compositions do not comprise an oxidizing agent.
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