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XENOBIOTICA · 2022 · IF 1.997

2-Naphthalenemethanol participates in metabolic activation of 2-methylnaphthalene

Kunna Li,Ying Zou,Yang Wang,Mengyue Zhou,Jing Li,Rong Tan,Shiyu Zhang,Weiwei Li,Jiang Zheng

2-Methylnaphthalene (2-MN) is an environmental pollutant. Studies have shown that 2-MN is teratogenic, carcinogenic, and cytotoxic. However, the mechanisms of 2-MN induced toxicities remain unclear.This study aimed to characterise reactive metabolites of 2-MN, to define the metabolic pathway, and to determine the enzymes participating in the metabolic activation.A hydroxylation metabolite of 2-MN, 2-naphthalenemethanol (2-NM), was observed in 2-MN-containing mouse liver microsomes.A glutathione (GSH) conjugate was detected in mouse S9 incubations fortified with 2-MN and GSH. A GSH conjugate and an NAC conjugate were found in mouse liver and urine, respectively, in animals given 2-MN. Hepatic protein covalent binding derived from 2-NM was observed in animals administered 2-MN.Cytochrome P450 enzymes and sulfotransferases participated in the metabolic activation of 2-MN.

CAS / MDL: 616-91-1
研究领域: 环境毒理学 · 药理学 · 生物化学
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JOURNAL OF SOLID STATE CHEMISTRY · 2021 · IF 3.498

Insights into varying dimension structures for deep-UV optical crystals NaBa2Al(P2O7)2 and NaBaAl(PO4)2 constructed separately from unique [Al(P2O7)2] chains and [Al(PO4)2] layers

Fang Wang,Xiao-Ni Yao,Yao Guo,Liguo Yang,Yi-Gang Chen,Xian-Ming Zhang

Two new metal aluminium phosphate millimetre-crystals NaBa 2 Al(P 2 O 7 ) 2 and NaBaAl(PO 4 ) 2 were successfully grown by using high-temperature molten method. The crystals NaBa 2 Al(P 2 O 7 ) 2 and NaBaAl(PO 4 ) 2 are located in space groups P ¯1 and P 2 1 /c, respectively. NaBa 2 Al(P 2 O 7 ) 2 displays a [Al(P 2 O 7 ) 2 ] 1D chain structure constructed from corner-sharing linkage of novel AlP 4 O 16 9− anion groups, and the AlP 4 O 16 9− group is formed by edge-sharing connection of two P 2 O 7 dimers and one AlO 6 octahedron . However, NaBaAl(PO 4 ) 2 exhibits a new [Al(PO 4 ) 2 ] 2D layer structure composed of AlP 2 O 10 7− anion groups via corner-sharing, and the AlP 2 O 10 7− group is generated by alternate linkages of corner-sharing PO 4 and AlO 4 tetrahedra. Analysis based on Pauling's electrostatic rule and Brown's bond valence model finds that structural feature of the two anion groups is mainly responsible for their different dimension structures in addition to structure-directed role of large Ba 2+ . The two crystals manifest a deep-UV optical transparency below 190 ​nm and good thermal stability, making them a potential optical window material. First-principles calculations reveal that the optical bandgaps of both crystals are determined by the Ba–O groups, rather than Al–O and P–O common groups.

研究领域: 材料科学 · 光学 · 晶体学
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JOURNAL OF CHEMICAL SCIENCES · 2024 ·Vol. 136 ·期 3 ·1-11 · IF 1.7

Recycled Pb/C-catalyzed one-pot synthesis of 1-carbonyl-1H-indoles from 2-iodoanilines and calcium carbide

Zhao Zhicai

A series of 1-carbonyl-1 H -indoles were prepared by 2-iodoanilines and calcium carbide in a one-pot reaction catalyzed by recyclable10% Pb/C, resulting in the corresponding substituted indoles in good yields. This protocol offers several advantages, including the utilization of sustainable, low-cost calcium carbide, an easy-to-handle acetylene source, and recyclable Pb/C catalysts. Graphic abstract The synthesis of a series of 1-carbonyl-1 H -indoles were prepared by 2-iodoanilines and calcium carbide in a one-pot reaction catalyzed by 10% Pb/C, resulting in the corresponding substituted indoles in good yields. This protocol offers several advantages, including the utilization of sustainable, low-cost feedstock, an easy-to-handle acetylene source, and recyclable Pb/C catalysts.

研究领域: 有机化学 · 绿色化学
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APPLIED AND ENVIRONMENTAL MICROBIOLOGY · 2017 ·Vol. 83 ·期 10 · IF 3.807

Biosynthesis of 2′-Chloropentostatin and 2′-Amino-2′-Deoxyadenosine Highlights a Single Gene Cluster Responsible for Two Independent Pathways in Actinomadura sp. Strain ATCC 39365

Yaojie Gao,Gudan Xu,Pan Wu,Jin Liu,You-sheng Cai,Zixin Deng,Wenqing Chen

2′-Chloropentostatin (2′-Cl PTN, 2′-chloro-2′-deoxycoformycin) and 2′-amino-2′-deoxyadenosine (2′-amino dA) are two adenosine-derived nucleoside antibiotics coproduced by Actinomadura sp. strain ATCC 39365. 2′-Cl PTN is a potent adenosine deaminase (ADA) inhibitor featuring an intriguing 1,3-diazepine ring, as well as a chlorination at C-2′ of ribose, and 2′-amino dA is an adenosine analog showing bioactivity against RNA-type virus infection. However, the biosynthetic logic of them has remained poorly understood. Here, we report the identification of a single gene cluster (ada) essential for the biosynthesis of 2′-Cl PTN and 2′-amino dA. Further systematic genetic investigations suggest that 2′-Cl PTN and 2′-amino dA are biosynthesized by independent pathways. Moreover, we provide evidence that a predicted cation/H+ antiporter, AdaE, is involved in the chlorination step during 2′-Cl PTN biosynthesis. Notably, we demonstrate that 2′-amino dA biosynthesis is initiated by a Nudix hydrolase, AdaJ, catalyzing the hydrolysis of ATP. Finally, we reveal that the host ADA (designated ADA1), capable of converting adenosine/2′-amino dA to inosine/2′-amino dI, is not very sensitive to the powerful ADA inhibitor pentostatin. These findings provide a basis for the further rational pathway engineering of 2′-Cl PTN and 2′-amino dA production.IMPORTANCE 2′-Cl PTN/PTN and 2′-amino dA have captivated the great interests of scientists, owing to their unusual chemical structures and remarkable bioactivities. However, the precise logic for their biosynthesis has been elusive for decades. Actually, the identification and elucidation of their biosynthetic pathways not only enrich the biochemical repertoire of novel enzymatic reactions but may also lay solid foundations for the pathway engineering and combinatorial biosynthesis of this family of purine nucleoside antibiotics to generate novel hybrid analogs with improved features.

研究领域: 微生物学 · 分子生物学 · 药物化学
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Polymer Chemistry · 2020 ·Vol. 11 ·期 25 ·4164-4171 · IF 5.342

Synthesis of cyclic poly(2-ethyl-2-oxazoline) with a degradable disulfide bond

Muhammad Waqas Ali,Zahir Muhammad,Qun Jia,Lianwei Li,Muhammad Saleem,Muhammad Siddiq,Yougen Chen

Cyclic poly(2-ethyl-2-oxazoline) (PEtOx) with a degradable disulfide bond has been synthesized by combining cationic ring opening polymerization (ROP) and reversible thiol/disulfide exchange chemistry. In greater detail, a living linear PEtOx with two cationic propagating terminals was initially synthesized using 1,3-bis(bromomethyl)benzene as a difunctional initiator. Both the living ends of PEtOx were then reacted with potassium ethyl xanthate to afford α,ω-xanthate end-functionalized PEtOx (xanthate-PEtOx-xanthate). The xanthate groups were then in situ cleaved using n-butylamine as a cleaving agent as well as a base in the same reaction media, which produced α,ω-thiol end-functionalized PEtOx (HS-PEtOx-SH). The cyclic polymer was eventually obtained by the successive intramolecular oxidation coupling of the thiol terminals of HS-PEtOx-SH to form a disulfide bond as a ring-closure link. For the polymeric information, 1H NMR spectroscopy, SEC spectroscopy, MALDI-TOF-MS, and UV-visible spectroscopy were combined to characterize the linear and cyclic polymers. Ellman's assay was used to determine the thiol content in the cyclic and thiol terminated polymers. Clean cyclic PEtOxs with number-average molar masses around 2000 (2 K) and 4000 (4 K) g mol−1 were obtained at an unreported high polymer concentration of 5 g L−1 (ca. 2.5 × 10−3 M for the 2 K polymer and ca. 1.25 × 10−3 M for the 4 K polymer) in THF. In addition, the synthetic route was compared with the intramolecular copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction and proven to be more advantageous in terms of reactant concentration, yield, purification, and bonding reversibility.

CAS / MDL: 140-89-6
研究领域: 高分子化学 · 材料科学
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MICROPOROUS AND MESOPOROUS MATERIALS · 2023 · IF 5.2

Separation of 2-Phenylethanol from 1-Phenyl-2-propanol and 2-Ethylphenol by metal-organic framework functionalized with amino groups

Yanyang Wu,Jiabo Rao,Qing Yi,Zhihui Ma,Bin Wu,Kui Chen,Lijun Ji

Metal-organic frameworks (MOFs) with sensitive nanospace and selective binding sites are widely used to discriminate the subtle structural. Adsorption performances of 2-Phenylethanol, 1-Phenyl-2-propanol, and 2-Ethylphenol on MOFs were studied in this paper. Eight MOFs were prepared hydrothermally and NH 2 -UiO-66(1) was chosen as the subsequent adsorbent based on the larger selectivity for both 1-Phenyl-2-propanol/2-Phenylethanol and 2-Ethylphenol/2-Phenylethanol. Studies on adsorption kinetics showed that pseudo-first-order model was suitable for adsorption performances of 1-Phenyl-2-propanol on NH 2 -UiO-66(1), while pseudo-second-order model was suitable for both 2-Phenylethanol and 2-Ethylphenol. The adsorption isotherm revealed that Langmuir model was suitable for 1-Phenyl-2-propanol, 2-Ethylphenol, and 2-Phenylethanol. Thermodynamic parameters including Gibbs free energy, enthalpy, and entropy indicated that adsorption of 1-Phenyl-2-propanol on NH 2 -UiO-66(1) was a spontaneous and exothermic physisorption process, while those of 2-Ethylphenol and 2-Phenylethanol were spontaneous and endothermic physisorption processes. The adsorption process indicated that the separation of 2-Phenylethanol from 1-Phenyl-2-propanol and 2-Ethylphenol on NH 2 -UiO-66(1) was due to the Lewis acid-base interactions and sieving effect. NH 2 -UiO-66(1) was also treated the simulated enriched 2-Phenylethanol solutions and 99.5% 2-Phenylethanol was obtained. In conclusion, NH 2 -UiO-66(1) can be a feasible adsorbent to separate 2-Phenylethanol from 1-Phenyl-2-propanol and 2-Ethylphenol for industrial application.

研究领域: 化学工程 · 材料科学 · 物理化学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2022 · IF 9.136

Efficient separation of high-abundance rare earth element yttrium and lanthanides by solvent extraction using 2-(bis((2-ethylhexyl)oxy)phosphoryl)-2-hydroxyacetic acid

Jinglu Han,Guolong Wu,Yanling Li,Songsong Li,Wuping Liao

To overcome the drawbacks such as emulsification and esterification reaction of the extractant and phase modifiers of the commonly used naphthenic acid (NA) system for yttrium (Y) separation, some novel extractants have to be developed. By combining the functional groups of commercial organophosphorus extractants, carboxylic acids and alcohol phase modifiers, a novel extractant 2-(bis((2-ethylhexyl)oxy)phosphoryl)-2-hydroxyacetic acid (HPOAc, HL) was designed and synthesized. The p K a value of HPOAc is a little larger than that of 2-ethylhexyl phosphoric acid mono-2-ethylhexylester (P507) and smaller than that of common carboxylic acid extractants such as NA and sec -octylphenoxy acetic acid (CA−12). Y(III) is the most difficult to be extracted among trivalent rare earth elements (REEs(III)) by HPOAc. The distribution ratios exhibit a distinct “tetrad effect”. The extraction mechanism follows a cation exchange mechanism with the extraction complex being deduced as REL 3 . Compared with NA and CA−12, HPOAc has higher extraction ability for REEs(III), and better performance in the separation of Ln(III) and Y(III). The extraction capacity for Y(III) is about 1.75 times higher than those of NA and CA−12. The loaded Y(III) and Sm(III) can be completely stripped by 0.75 mol/L HCl solution. Moreover, even if the organic phase is saturated or there are several impurity metal ions (Mg(II), Al(III), Ca(II), Mn(II) and Zn(II)) in the aqueous solution, two phases can still be separated very quickly and the fluidity of the loaded organic phase is good without the phase modifiers. Encouragingly, the HPOAc system also exhibits good separation performance towards REEs(III) and the impurity metal ions. Finally, a cascade extraction process for separating Ln(III) and Y(III) was developed using HPOAc as the extractant. The Y product with the purity of 99.31 wt% was obtained by 20 stages of extraction and 4 stages of scrubbing.

CAS / MDL: 563-96-2
研究领域: 化学工程 · 材料科学
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JOURNAL OF MATERIALS SCIENCE · 2018 ·Vol. 54 ·期 3 ·2037-2048 · IF 2.993

Formation and photoluminescence properties of colloidal ZnCuIn(SexS1 − x)2/ZnS nanocrystals with gradient composition

Wang Kelai,Liang Zheng,Li Jingling,Xu Xueqing,Cheng Xiaoling,Jin Hu,Xu Dehua,Xu Gang

Photoluminescent CuIn(Se x S 1 −  x ) 2 (CISeS) nanocrystals (NCs) have been synthesized utilizing copper iodide (CuI) and indium acetate (In(Ac) 3 ) as metal cation precursors, Se powder and n -dodecanethiol (DDT) as selenide and sulfur source, combined with oleylamine and n -dodecanethiol as coordinate ligands at a moderate reaction temperature of 200 °C. The obtained CISeS NCs consisted of a gradient composition that the content of selenide increased from the nuclei to the surface. With the growth of NCs, they exhibited a tunable photoluminescent emission ranging from 722 to 830 nm which was size- and composition-dependent. The photoluminescent quantum yield of the NCs could be further enhanced from 1.2 to 40.7% after ZnS coating due to the formation of ZnCuIn(Se x S 1 −  x ) 2 /ZnS (ZnCISeS/ZnS) core–shell structures with the alloyed core. The photoluminescence emission mechanisms of CISeS NCs indicated that the gradient composition structure of CISeS led to a gradient energy level of its conduction band (CB)/valence band (VB), resulting in the charge transfer from the nuclei to the surface through the quantized CB/VB. This transfer process has quenched fluorescence emission arising from the quantized CB/VB and defect states located in the nuclei, such as irradiation relaxation between quantized CB and \( V_{\text{Cu}}^{ \prime } \) . This mechanism could illuminate why the indium-rich CISeS NCs did not exhibit better photoluminescence properties.

研究领域: 材料化学 · 纳米科学 · 半导体光学 · 光电子学 · 胶体化学 · 能源材料
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Nature Communications · 2023 ·Vol. 14 ·期 1 ·1-14 · IF 16.6

Anti-VEGFR2 F(ab′)2 drug conjugate promotes renal accumulation and glomerular repair in diabetic nephropathy

Liu Di,Song Yanling,Chen Hui,You Yuchan,Zhu Luwen,Zhang Jucong,Xu Xinyi,Hu Jiahao,Huang Xiajie,Wu Xiaochuan,Xu Xiaoling,Jiang Saiping,Du Yongzhong

Poor renal distribution of antibody-based drugs is the key factor contributing to low treatment efficiency for renal diseases and side effects. Here, we prepare F(ab′) 2 fragmented vascular endothelial growth factor receptor 2 antibody (anti-VEGFR2 (F(ab′) 2 ) to block VEGFR2 overactivation in diabetic nephropathy (DN). We find that the anti-VEGFR2 F(ab′) 2 has a higher accumulation in DN male mice kidneys than the intact VEGFR2 antibody, and simultaneously preserves the binding ability to VEGFR2. Furthermore, we develop an antibody fragment drug conjugate, anti-VEGFR2 F(ab′) 2 -SS31, comprising the anti-VEGFR2 F(ab′) 2 fragment linked to the mitochondria-targeted antioxidant peptide SS31. We find that introduction of SS31 potentiates the efficacy of anti-VEGFR2 F(ab′) 2 . These findings provide proof of concept for the premise that antibody fragment drug conjugate improves renal distribution and merits drug validation in renal disease therapy.

研究领域: 药理学 · 肾病学 · 糖尿病
✓ 已验证 DOI PubMed 高影响因子
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Bioresources and Bioprocessing · 2018 ·Vol. 5 ·期 1 ·1-11 · IF 0

2-Hydroxy-4-(3′-oxo-3′H-benzofuran-2′-yliden)but-2-enoic acid biosynthesis from dibenzofuran using lateral dioxygenation in a Pseudomonas putida strain B6-2 (DSM 28064)

Liu Xin,Wang Weiwei,Hu Haiyang,Lu Xinyu,Zhang Lige,Xu Ping,Tang Hongzhi

Background Benzofuran and its derivatives contain central pharmacophores and are important structures in medicinal chemistry. Chemical synthesis of benzofuran rings often requires expensive catalysts and stringent operational conditions. Biosynthesis is recognized as a promising way to save energy and produce valuable compounds. Dioxin biodegradation pathways can form several benzofuran derivatives, and these pathways may be a better choice for further synthesis of important biological compounds. 2-Hydroxy-4-(3′-oxo-3′ H -benzofuran-2′-yliden)but-2-enoic acid (HOBB), a benzofuran derivative, can be biosynthesized from dibenzofuran (DBF) through co-metabolic degradation in a lateral dioxygenation pathway. Results Efficient biosynthesis of HOBB was observed using whole cells of Pseudomonas putida strain B6-2. After cultivation in LB medium containing biphenyl, the cells were suspended to an OD 600 of 5 to conduct biosynthesis in the presence of 0.5-mM DBF at pH 7 for 8 h. The bacterial cells were used twice to degrade approximately 0.70-mM DBF, and in batch process, accumulated about 0.29-mM HOBB. HOBB could be easily purified from the reaction with ethyl acetate using the neutral-acid extraction method, and 13.58 ± 0.31 mg of HOBB was obtained from 22.49 ± 0.74-mg DBF with an overall production yield of 60.4% (w/w). The product HOBB, which is a yellow powder, could be detected and identified by LC–MS, GC–MS, and NMR. Conclusions In this study, a new biological route was developed to produce HOBB from DBF using whole cells of P. putida B6-2 (DSM 28064). The biosynthesis of HOBB may contribute to studies of the DBF lateral pathway and provide a new green route for synthesizing benzofuran derivatives with pharmacological activities.

CAS / MDL: 68-12-2 64-18-6 67-56-1
研究领域: 环境生物学 · 药学 · 微生物学
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JOURNAL OF MOLECULAR STRUCTURE · 2021 · IF 3.196

Sr5(CO3)2(BO3)2: A new family member of isostructural mixed borate and carbonate Ba4M(BO3)2(CO3)2 (M = Ba, Sr) with isolated BO3 and CO3 groups

Jiongquan Chen,Zhihua Yang,Kui Wu,Yun Yang,Shilie Pan

A new mixed borate and carbonate Sr 5 (CO 3 ) 2 (BO 3 ) 2 , which is isostructural with Ba 4 M(BO 3 ) 2 (CO 3 ) 2 (M = Ba, Sr), has been synthesized by hydrothermal method . It crystallizes in Pnma (No. 61) space group with the lattice parameters a  = 7.387(4), b  = 16.556(9) and c  = 8.971(5) Å ( Z  = 4). This structure features a three-dimensional (3D) network including SrO 8 polyhedra, isolated BO 3 and CO 3 triangles. UV-Vis-NIR diffuse reflectance spectrum for Sr 5 (CO 3 ) 2 (BO 3 ) 2 indicates that it has a deep ultra-violet cut-off edge of 190 nm. In addition, crystal structural comparison among mixed borates and carbonates shows that the interaction between boron-oxide groups and CO 3 groups leads to different arrangements of anionic groups, which can be classified into three types according to the connection of boron-oxide groups. An analysis of theoretical calculations based on density functional theory was also performed to understand the relationships between the structures and properties.

研究领域: 材料科学 · 化学
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TETRAHEDRON · 2017 · IF 2.651

Metal-free visible-light-promoted intermolecular [2+2]-cycloaddition of 3-ylideneoxindoles

Ling-Ling Wu,Gao H. Yang,Zhi Guan,Yan-Hong He

The Rose Bengal sensitized intermolecular [2 + 2]-cycloaddition of 3-ylideneoxindoles for the synthesis of spirocyclic oxindoles was developed successfully under visible light irradiation conditions. The cycloaddition products were obtained in good yields (up to 93%) with excellent diastereoselectivity and regioselectivity by using a low loading of Rose Bengal (0.125 mol%) as a triplet sensitizer. This work demonstrates the potential benefits of Rose Bengal in visible light catalysis.

CAS / MDL: 632-69-9
研究领域: 有机化学 · 光化学
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