17057-04-4Relevant articles and documents
4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid: X-ray and DFT-calculated structure
Moreno-Fuquen, Rodolfo,Tenorio, Juan C.,Ellena, Javier,De Simone, Carlos A.,Ribeiro, Leandro
, p. o67-o70 (2011)
In the title compound, C11H7NO4, there is a dihedral angle of 45.80 (7)° between the planes of the benzene and maleimide rings. The presence of O - H...O hydrogen bonding and weak C - H...O inter-actions allows the formation of R33(19) edge-connected rings parallel to the (010) plane. Structural, spectroscopic and theoretical studies were carried out. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) and 6-31++G(d,p) levels are compared with the experimentally determined mol-ecular structure in the solid state. Additional IR and UV theoretical studies allowed the presence of functional groups and the transition bands of the system to be identified.
Covalent conjugation of single-walled carbon nanotube with CYP101 mutant for direct electrocatalysis
Ray, Moumita,Mhaske, Sanjay D.,Haram, Santosh K.,Mazumdar, Shyamalava
, (2021)
Covalent linkage between the single-walled carbon nanotube (SWCNT) and CYP101 through a specific site of the enzyme can provide a novel method of designing efficient enzyme electrodes using this prototype cytochrome P450 enzyme. We have chemically modified the SWCNT with linker 4-carboxy phenyl maleimide (CPMI) containing maleimide functional groups. The enzyme was covalently attached on to the SWCNT through the maleimide group of the linker (CPMI) to the thiolate group of the surface exposed Cys 58 or Cys 136 of the CYP101 forming a covalently immobilized protein on the nanotube. Thin film of the modified SWCNT-CPMI-CYP101conjugate was made on a glassy carbon (GC) electrode. Direct electrochemistry of the substrate (camphor)-bound enzyme was studied using this immobilized enzyme electrode system and the redox potential was found to be ?320mV vs Ag/AgCl (3 M KCl), which agrees with the redox potential of the substrate bound enzyme reported earlier. The electrochemically driven enzymatic mono-oxygenation of camphor by this immobilized enzyme electrode system was studied by measurement of the catalytic current at different concentrations of camphor. The catalytic current was found to increase with increasing concentration of camphor in presence of oxygen. The product formed during the catalysis was identified by mass-spectrometry as hydroxy-camphor.
Preparation and characterization of new carrier drug polymers based maleimide and its drug release behaviour
Mageed, Fatimah Abdul Razzak,Kareem, Mohanad Musa,Al-Baiati, Mohammad N.
, p. 569 - 574 (2019)
In this work, two new drug substituted monomers and new homogenous and heterogeneous polymers were synthesized loaded with medicinal properties to extend the controlled drug. The first step includes preparation of compound (F1) via reaction of maleic anhydride with 4-aminobenzoic acid. Then compound (F1) was converted to its corresponding acyl chloride derivative which reacted with amino drugs (sulfadiazine, chlordiazepoxide) afforded (F2 and F3) monomers. Homogeneous polymers (F8 and F9) prepared through polymerization reaction of free radicals of the monomers (F2 and F3) under nitrogen using methyl ethyl ketone peroxide (MEKP) as initiator. Heterogeneous polymers (F14 and F15) prepared through polymerization reaction of free radicals of the monomers (F2 and F3) separately with acrylic acid under nitrogen using methyl ethyl ketone peroxide (MEKP) as initiator. All these prepared monomers and polymers were characterized by FT-IR and 1H NMR, 13C NMR spectroscopies. Controlled drug release and swelling % was studied in different pH values at 37 oC. Intrinsic viscosities were measured at 25 oC with Ostwald viscometer and applied the characteristic of solubility for these polymers.
Maleimide copolymers containing azobenzene moieties-synthesis and study of liquid crystalline and optical properties
Cozan, Vasile,Hulubei, Camelia,Airinei, Anton,Morariu, Simona
, p. 101900 - 101910 (2016)
New reactive copolymers have been synthesized by copolymerization of two functional N-substituted-maleimides with styrene. These copolymers, with aldehyde and carboxyl functional groups, were further chemically modified with p-aminoazobenzene. After verification of the chemical structures by IR and 1H-NMR spectroscopy, the copolymers were characterized by solubility, X-ray diffraction measurements and their thermal stability was controlled by thermogravimetrical analysis (TGA). The thermal and thermotropic properties were investigated using polarizing optical microscopy (POM) and differential scanning calorimetry (DSC). A comparative study of the photoisomerization in solution and thermal recovery characteristics of azo copolymers vs. the corresponding maleimide model compound has been performed.
Synthesis and evaluation of a novel fluorescent chemosensor for glutathione based on a rhodamine B and N-[4-(carbonyl) phenyl]maleimide conjugate and its application in living cell imaging
Shu, Hai,Wu, Xiaolei,Zhou, Baojing,Han, Yingbin,Jin, Mingjie,Zhu, Jing,Bao, Xiaofeng
, p. 535 - 542 (2017)
A novel rhodamine B spirolactam derivative bearing an N-[4-(carbonyl)phenyl] maleimide moiety (L1) was designed, synthesized and structurally characterized to develop a chemosensor. The interactions of L1 with amino acids and metal ions were studied by UV–vis absorption and fluorescence spectroscopy. L1 exhibited a highly sensitive and selective turn-on fluorescence response toward glutathione (GSH) over other biological species in EtOH/HEPES (3:2, v/v, 0.1?mM, pH 7.34) solution. The detection limit of GSH by L1 was 0.219?μM. Intracellular imaging applications demonstrated that L1 can be used as a fluorescent probe for the detection of GSH in HepG-2 and HUVEC cells.
p-Aminobenzoic acid derivatives as acetylcholinesterase inhibitors
Correa-Basurto, Jose,Alcantara, Ivan Vazquez,Espinoza-Fonseca, L. Michel,Trujillo-Ferrara, Jose G.
, p. 732 - 735 (2005)
Because Alzheimer's disease (AD) is a medical problem characterized by progressive loss of memory and cognition that is associated with a deficient cholinergic system, this work aims to evaluate some p-aminobenzoic acid (PABA) derivatives as acetylcholinesterase inhibitors in vitro, in continuation with our last studies. The assayed compounds are low toxic, simple-structured and low cost.
A NIR facile, cell-compatible fluorescent sensor for glutathione based on Michael addition induced cascade spirolactam opening and its application in hepatocellular carcinoma
Yang, Xin,Qian, Ying
, p. 7486 - 7494 (2018)
A NIR fluorescence probe with long emission wavelength at 746 nm and high quantum yield of 0.36 was designed and synthesized to selectively detect GSH over Hcy and Cys in living systems. 2-(1,3,3-Trimethylindolin-2-ylidene)acetaldehyde was attached to rhodamine by Knoevenagel condensation to shift the emission to near infrared region. Then, ethylenediamine was linked to M2 get an important intermediate M3. Finally, target molecule named RhNM was synthesized through combined N-[4-(carbonyl)phenyl] with M3. RhNM shows excellent discrimination in detecting GSH from Hcy/Cys along with an obvious color change. The fluorescence band at 746 nm is rapidly enhanced 106-fold after adding GSH, and the quantum was calculated at 0.36. Titration experiments of GSH showed good linear relationship of intensity vs. GSG concentration, and the detection limit was calculated at 70 nM. The proposed mechanism for identifying GSH based on Michael addition involves reactions of the carbon-carbon double bond and subsequent spirolactam opening. Meanwhile, the probe RhNM can work in a wide range of pH of 4-10. The probe RhNM was used for endogenous and exogenous imaging in HepG2 cells for glutathione. There was an outstanding intracellular red fluorescence occurring upon the addition of GSH incubated with HepG2 cells. It has been successfully applied for the determination of GSH in diluted serum and for bio-imaging of GSH in living cells with low cell toxicity. All results indicated that the probe can be used as an ultra-sensitive, near-infrared fluorescent chemical sensor for selectively detecting GSH in living cell. It has great potential in imaging of live tissues and even, animal imaging.
Thermal degradation kinetics and thermodynamics of maleimide-sytrene based alternating copolymer: A comparative investigation of monomer and polymer structures
Ak, Metin,Koyundereli ??lg?, Gülbanu
, (2020)
Thermal degradation of N-(4-(3-Thienyl methylene)-oxycarbonylphenyl) maleimide monomer, MT and its copolymer with styrene, P(MT-alt-St) were investigated comparatively using TG and DTA methods. Degradation of monomer takes place in three stages which correspond to removal of thiophene, aliphatic groups and the rest of structural decomposition respectively. Degradation of the copolymer occurs in two stages. Thiophene and aliphatic groups decompose simultaneously at the first degradation stage. The main polymeric chain remains intact. The second stage is related to the rest of structural decomposition. Activation energy values of these reactions were calculated by using Flynn-Wall-Ozawa (FWO) and Kissinger-Akahira-Sunose (KAS) methods. In order to determine the effective reaction model and calculate thermodynamic parameters, these methods were combined with modeling equations. It was found that the first degradation stages of monomer and copolymer show good harmony with diffusion model (D1), whereas nucleation and growth model (A2) is effective for the second decomposition stage of the monomer.
1,3-dipolar cycloaddition: Free catalytic synthesis and esophageal cancer activity of new 1,2,3-triazole-oxydianiline-maleimide hybrids
Mohammed, Mohammed K.,Almashal, Faeza A.,Jassem, Ahmed M.
, p. 47 - 53 (2021/01/18)
A new series of 1,2,3-triazole-oxydianiline-maleimide hybrids 12-15 was synthesized by using 1,3-dipolar cycloaddition reaction of N-Arylmaleimides 6-9 with 4,4'-oxybis(azidobenzene) 11 under an efficient and free catalytic reaction. All the newly synthesized hybrids were characterized by their 1H NMR, F-TIR, Mass spectral data and melting points. The cytotoxic activities (in vitro) of selected hybrids against esophageal cancer of human cell line (SKG) were evaluated by MTT assay. Among them, hybrid 13 exhibited a potent inhibition activity with the IC50 value of 1.61±0.01 μM against esophageal cancer cell (SKG). Cellular mechanism investigations in esophageal carcinoma cells (SKG) elucidated that hybrid 13 inhibited cell growths in vitro and arrested cell cycle at an environmental phase. These results revealed that hybrid 13 holds a promising anticancer agent with the enhancement of further clinical applications in drug discovery field.
Synthesis, characterization, and targeted chemotherapy of SCT200-linker-monomethyl auristatin E conjugates
Hu, Xinyue,Jiang, Hailun,Bai, Weiqi,Liu, Xiujun,Miao, Qingfang,Wang, Linlin,Jin, Jie,Cui, Along,Liu, Rui,Li, Zhuorong
supporting information, (2021/03/08)
Antibody-drug conjugates (ADCs) are currently among the most successful and important strategies for treating patients with solid tumors. ADCs are composed of a monoclonal antibody and warhead, which are conjugated via a linker. Currently, monomethyl auristatin E (MMAE) is the most widely applied warhead in the development of ADCs. However, MMAE-based ADCs are generally constructed using the MC-VC-PABC linker, and this design has limited structural diversity and some disadvantages. Accordingly, in this study, we generated three types of novel linker-MMAE (with alterations in the spacer, catabolizing area, and self-immolative compared with MC-VC-PABC-MMAE) in ADCs, termed SCT200-linker-MMAE conjugates, and then evaluated the linker-drug plasma stability and the rate of drug release by cathepsin B. The binding ability, internalization rates, and efficacy of all SCT200-linker-MMAE ADCs were systematically studied, and the expression of apoptosis-associated proteins and the therapeutic efficacies of SCT200-M-2, -C-2, and -C-4 were evaluated. The results showed that the activities of some of these ADCs were increased for epidermal growth factor receptor-positive tumors. Moreover, the novel linkers designed in this study can be linked with other antibodies to treat other types of cancer. Overall, these findings provide important insights into the application of SCT200-based linkers in ADCs.
