- Naphthalimide Scaffold Provides Versatile Platform for Selective Thiol Sensing and Protein Labeling
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Reversible thiol modifications are fundamental of cellular redox regulation. Specific thiol detection, including thiol sensing and protein thiols labeling, is critical to study such modifications. We reported the discovery of 4-methylsulfonyl-N-n-butyl-1,8-naphthalimide (MSBN), a highly selective fluorogenic probe for thiols based on the 1,8-naphthalimide scaffold. Thiols react with MSBN nearly quantitatively via nucleophilic aromatic substitution to replace the methylsulfonyl group and restore the quenched fluorescence (>100-fold increase). MSBN was employed to selectively image thiols in live cells and specifically label protein thiols with a turn-on signal to determine diverse reversible protein thiol modifications. In addition, we introduced a bulky group into the MSBN as a mass tag to create a probe MSBN-TPP, which readily discriminates the reduced thioredoxin from the oxidized one. The specific reaction of MSBN with thiols and the easy manipulation of the naphthalimide unit enable MSBN a versatile scaffold in developing novel probes for thiol-based protein bioconjugation and studying various thiol modifications.
- Zhou, Pengcheng,Yao, Juan,Hu, Guodong,Fang, Jianguo
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- Influence of electron donors in fluorescent NLOphoric D-π-A derivatives with acenaphthene rotor: Photophysical, viscosity, and TD-DFT studies
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The novel fluorescent NLOphoric push-pull fluorophores (2a-c) constituted by the different N-substituted donors linked via π-bridge as a spacer to 1,1′-dicyanomethylidene group as an acceptor with acenaphthene rotor were synthesized and characterized. These dyes exhibit positive absorption and emission solvatochromism in solvents of different polarities. Solvent polarity plots viz. Lippert-Mataga, McRae, and Weller models provide the validation of charge transfer (CT) characteristics whereas, the Rettig model furnishes an alternative relaxation channel due to twisting around the σ-bonds between donor and acceptor on photoexcitation leading to the twisted intramolecular charge transfer (TICT) state in 2a-c. Viscosity induced emission studies show 4.40, 8.78, and 5.63 fold increase in the emission intensity for dyes 2a, 2b, and 2c respectively which recommends the titled dyes as a fluorescent molecular rotor (FMR). Density Functional Theory (DFT) calculations [(B3LYP/6-311++G(d,p)] give complete information of structural as well as electronic properties of dyes 2a-c. The large difference in dipole moment (ca. 7.92–20.0 D) results in a strong non-linear optical (NLO) properties. The NLO properties were estimated theoretically as well as spectroscopically in solvents of different polarities. The computed values for these dyes show high first-order hyperpolarizability (β) in the range of 210–577 × 10?3° esu and second-order hyperpolarizability (γ) in the range of 506-2,325 × 10-36 esu.
- Mohbiya, Dhanraj R.,Mallah, Ramnath R.,Sekar, Nagaiyan
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- Homocondensation of 1,3-di(5-acenaphthenyl)but-2-ene-1-one
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Homocondensation of 1,3-di(5-acenaphthenyl)but-2-en-1-one obtained by dimerization of 5-acetylacenaphthene leads to 1,3,5-tri(5-acenaphthenyl)benzene. No alternative product, 1,3,5,7-tetra(5-acenaphthenyl)cyclooctatetraene, was formed.
- Khotina, I. A.,Kovalev, A. I.
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p. 1994 - 1996
(2021/11/05)
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- Aromatic heterocyclic modified naphthalimide derivative as well as preparation method and application thereof
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The invention discloses an aromatic heterocyclic modified naphthalimide derivative, which has a structural general formula as shown in I, a skeleton is novel, the derivative has high efficiency and low toxicity, and good inhibitory activity on tumor cells. The invention also discloses a preparation method of the compound, which comprises the following steps: by using naphthalimide as a raw material, respectively introducing active groups imidazopyridine and aminothiazole into the parent naphthalene ring to synthesize a new aromatic heterocyclic modified naphthalimide pharmacophore, modifying with a polyamine chain, designing and synthesizing a series of naphthalimide derivatives modified with imidazopyridine and aminothiazole. The compound retains the antitumor activity of naphthalimide and also has the characteristics of imidazopyridine and aminothiazole, the biological activity of original molecules is improved, and the antitumor activity of target molecules is improved. The invention also provides an application of the compound in preparation of antitumor drugs, and the compound shows good development potential.
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Paragraph 0044; 0047
(2021/01/29)
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- Naphthalimide-polyamine conjugate as well as preparation method and application thereof
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The invention discloses a naphthalimide-polyamine conjugate, which has a structural general formula as shown in I, a novel skeleton, high efficiency, low toxicity and good inhibitory activity for tumor cells. The invention also discloses a preparation method of the conjugate. Firstly, 3-amino groups with toxic and side effects of amonafide are removed, a phenylpyrazole structure fragment is introduced to the naphthalimide parent naphthalene ring, and a naphthalimide side chain with a polyamine chain is modified, acetyltransferase in vivo is prevented from acetylating the amino groups on the naphthalene ring of amonafideand, and toxic and side effects are reduced; and further by introducing a low-toxicity phenyl pyrazole active structure fragment, the naphthalimide polyamine conjugate witha novel skeleton, high efficiency and low toxicity is synthesized; and secondly, quinazoline with low toxicity is introduced to replace hydrogen atoms of amonafide 3-amino, so that the naphthalimide polyamine conjugate with anti-tumor activity and low toxicity is obtained. The invention also discloses an application of the conjugate in preparation of antitumor drugs, and good development potentialis realized.
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Paragraph 0021; 0044-0047
(2021/02/10)
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- Combining viscosity-restricted intramolecular motion and mitochondrial targeting leads to selective tumor visualization
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We report a novel fluorescent molecular conjugate, V-M1, enabling an accurate visualization of tumor tissues. The emission wavelength of V-M1 exceeds 650 nm, which is well within the near-infrared therapeutic window. Tumor accumulation of this cationic dye allows the visualization of cancerous cells as a function of mitochondrial viscosity.
- Jiang, Dewei,Kim, Jong Seung,Li, Mingle,Verwilst, Peter,Yu, Le,Zhang, Jun Feng,Zhou, Ying
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supporting information
p. 6684 - 6687
(2020/07/03)
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- Palladium catalyzed decarboxylative acylation of arylboronic acid with ethyl cyanoacetate as a new acylating agent: Synthesis of alkyl aryl ketones
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Palladium catalyzed acylation of arylboronic acid containing various functional groups was performed efficiently by ethyl cyanoacetate/substituted ethyl cyanoacetate as the acylating agent in aqueous triflic acid medium. The alkyl aryl ketones were obtained in good to excellent yields, first by addition of arylboronic acid to the nitrile group of ethyl cyanoacetate and their derivatives, followed by in situ decarboxylation of the resulting β-ketoester.
- Yousuf, Md,Das, Tuluma,Adhikari, Susanta
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p. 8763 - 8770
(2015/11/10)
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- Synthesis and enantiomer separation of 5-(1-(3,5-Dinitrobenzoylamino)pent-4-enyl)acenaphthene
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A new racemic (±) 5-(1-(3,5-dinitrobenzoylamino)pent-4-enyl)-acenaphthene was synthesized and successfully separated into enantiomers on chiral HPLC. The synthetic approach to the 5-(1-(3,5- dinitrobenzoylamino)pent-4-enyl)acenaphthene is via Friedel-Crafts acylation reaction to the acenaphthyl ring, α-H substituent reaction to the ketone, deoxidization reaction to the ketone and amidation reaction to the amidocyanogen. The chemical structure of this compound was characterized by FT-IR and 1H NMR.
- Xu, Chao,Luo, Wen-Feng,Li, Li-Jun,Yao, Shun,Song, Hang
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experimental part
p. 3923 - 3928
(2010/11/16)
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- Reduction of diaryl alkenes by hypophosphorous acid-iodine in acetic acid
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A mixture of 50% aqueous H3PO2 and I2 (in catalytic amount) in HOAc efficiently reduces aryl alkenes to the corresponding alkanes in high yield. Addition of acetic anhydride to the medium results in ring-acetylation (or N-acetylation in the case of amines). H3PO2 costs only one-fifth as much as hydriodic acid on a mole basis and one mole of H3PO2 produces four moles of HI, resulting in a 20-fold cost advantage for H3PO2/I2 over aqueous HI as a source of HI.
- Fry, Albert J.,Allukian, Myron,Williams, Allison D.
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p. 4411 - 4415
(2007/10/03)
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- Reaction of substituted 5-bromoacenaphthenes with the catalytic reduction system NiCl2-2,2'-bipyridyl (or 1,10-phenanthroline)-Zn
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Transformations of substituted 5-bromoacenaphthenes under the action of a catalytic reduction system NiCl2-2,2'-bipyridyl (or 1,10-phenanthrolyne)-Zn in DMF and DMA was studied. Two types of transformation are shown to be characteristic for the studied compounds: reductive coupling with formation of the corresponding 5,5'-biacenaphthenyl and halogen elimination with hydrogen replacing the halogen. Yields of the coupling products and that of dehalogenation are found to depend substantially on the nature of the substituents in the nanhfhalene ring.
- Adonin,Ryabinin,Starichenko
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p. 913 - 915
(2007/10/03)
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- Synthesis of pentathiepanes and isolation of the conformers based on high inversion barrier of the pentathiepane ring
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Acenaphtho[1,2-a]acenaphthylene (1) was sulfurated with elemental sulfur to give a pentathiepane derivative (2). A dynamic NMR spectrum analysis revealed that the two naphthalene rings of 2 are chemically nonequivalent up to 100 °C. The pentathiepane ring
- Sugihara, Yoshiaki,Takeda, Hitoshi,Nakayama, Juzo
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p. 597 - 605
(2007/10/03)
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- Flash vacuum thermolysis of 5-(1-chloroethenyl)acenaphthene. A short synthesis of pyracylene and its bechaviour under high temperature conditions
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Flash vacuum thermolysis (FVT) of 5-(1-chloroethenyl)acenaphthene (4) has been found to give rise to pyracylene (1).Pure 1 can be isolated from the 1100 deg C pyrolysate by recrystallization at -20 deg C.The temperature conversion data reveal that 1 decomposes and rearranges at T 1000 deg C; acenaphthylene (11), 1-ethynyl- (23) and 3-ethynyl-acenaphthylene (24) have been identified.The formation of 23 and 24 indicates that 1 rearranges to the transient cyclopentacenaphthylene (20) via a single ring-contraction-ring-expansion mechanism under FVT conditions.The experimental data are supported by semiempirical AM1 calculations of the C14H8 potential energy surface.
- Sarobe, Martin,Flink, Simon,Jenneskens, Leonardus W.,Zwikker, Jan W.,Wesseling, Jolanda
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p. 2125 - 2132
(2007/10/03)
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