10047-18-4Relevant articles and documents
Naphthalimide Scaffold Provides Versatile Platform for Selective Thiol Sensing and Protein Labeling
Zhou, Pengcheng,Yao, Juan,Hu, Guodong,Fang, Jianguo
, p. 1098 - 1105 (2016)
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.
Influence of electron donors in fluorescent NLOphoric D-π-A derivatives with acenaphthene rotor: Photophysical, viscosity, and TD-DFT studies
Mohbiya, Dhanraj R.,Mallah, Ramnath R.,Sekar, Nagaiyan
, p. 40 - 52 (2018)
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.
Aromatic heterocyclic modified naphthalimide derivative as well as preparation method and application thereof
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Paragraph 0044; 0047, (2021/01/29)
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.
Combining viscosity-restricted intramolecular motion and mitochondrial targeting leads to selective tumor visualization
Jiang, Dewei,Kim, Jong Seung,Li, Mingle,Verwilst, Peter,Yu, Le,Zhang, Jun Feng,Zhou, Ying
supporting information, p. 6684 - 6687 (2020/07/03)
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.