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溴苯基
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES · 2022 ·Vol. 238 ·期 1 ·13-14 · IF 0.365

The crystal structure of 1-(4-bromophenyl)-3-(2-chlorobenzyl)urea, C14H12BrClN2O

Zhihong Zhu,Lilei Zhang

C 14 H 12 BrClN 2 O, monoclinic, P 2 1 / c (no. 14), a  = 13.4072(6) Å, b  = 8.6103(5) Å, c  = 12.3824(6) Å, β  = 100.475(4), V  = 1405.60(12) Å 3 , Z  = 4, R gt ( F ) = 0.0499, wR ref ( F 2 ) = 0.1215, T = 173 K.

研究领域: 化学 · 晶体学
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BIOCHEMICAL ENGINEERING JOURNAL · 2024 · IF 3.7

Cordyceps fungus-mediated enantioselective synthesis of chiral alcohol and enhanced biocatalytic efficiency in cyclodextrin/surfactant-buffer system

Qian Gui,Hai-Min Zhang,Feng Qian,Han-Yu Liu,Xiang-Xin Kong,Guo-Ying Lv,Pu Wang

Asymmetric synthesis of chiral alcohols by biocatalysts holds promising prospect. In this study, a medicinal Cordyceps fungus, namely Tolypocladium inflatum , was adopted as a novel biocatalyst for the synthesis of chiral alcohols. Among the assessed prochiral ketone substrates, T. inflatum exhibited the best catalytic activity towards 1-(4-bromophenyl)−2,2,2-trifluoroethanone (BPFO), yielding a valuable pharmaceutical intermediate ( S )−1-(4-bromophenyl)−2,2,2-trifluoroethanol (( S )-BPFL) with >99.9 % enantiomeric excesses (ee). For more efficient biosynthesis of ( S )-BPFL, cyclodextrins or surfactants were introduced to the reaction system as additives to strengthen this bioprocess. Among which methyl β-cyclodextrin (MCD) improved cell membrane permeability and alleviated product inhibition, while Triton X-100 enhanced BPFO solubility. Furthermore, synergistic promotion for BPFO bioreduction by MCD and Triton X-100 was observed. Under the optimal reaction conditions, 50 mM BPFO was converted into ( S )-BPFL with 89.1 % yield and >99.9 % ee in 12 h, showing 16-fold increase of space-time yield in the developed MCD/Triton X-100-buffer system compared to neat buffer solution. This study illustrated the potential of the enantioselective preparation of chiral alcohols mediated by Cordyceps fungus. Additionally, the biocatalytic efficiency was significantly improved in the constructed synergistic reaction system, and the underlying mechanism was also explored.

CAS / MDL: 1306-23-6
研究领域: 生物催化 · 有机化学 · 药物化学
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Food Bioscience · 2025 · IF 5.9

Study on the mechanism of 1-(4-bromophenyl)5-phenyl-1h-1, 2, 3-triazole against Colletotrichum gloeosporioides in mango by chemical proteomics

Shuai Wang,Jiayang Li,Cong Xie,Wanhui Chen,Huajie Feng,Wenying He

Our previous study found that 1-(4-bromophenyl)-5-phenyl-1H-1,2,3-triazole (BPT) exhibited very low toxicity and higher biology activity. In the present study, BPT was used to investigate its mechanism against Colletotrichum gloeosporioides in mango by chemical proteomics and chemicobiological methods. The experimental results of some phenotypic traits and cytotoxicity indicated that there are some changes in permeability of the cell membranes and BPT has fungistatic activity with lower cytotoxicity. Next, a biotin probe named BPTN with a higher activity (EC 50 value of 11.08 mg/L) than that of BPT(EC 50 value of 14.13 mg/L) was designed and synthesized by the chemical proteomics approach. The major differentially expressed proteins between BPT or BPTN and Colletotrichum gloeosporioides were identified and analyzed by Matrix-assisted laser desorption time-of-flight mass spectrometry (MALDI-TOF-MS) and bioinformatics. The results indicated that there are 25 differentially expressed proteins in Colletotrichum gloeosporioides under BPT intervention, and 29 target proteins in Colletotrichum gloeosporioides captured by BPTN. For BPTN-anthracnose system, the protein No. 8 belonged to cytochrome P450 proteins (CYP) family can be taken as a target protein of BPTN, which confirmed by bioinformatics analysis. Further, a classic fungal target protein of triazoles, sterol 14α-demethylase (CYP51) was used to verify the interaction in the presence of BPT by various spectroscopic and molecular docking methods. The results showed that BPT exhibited strong interactions with CYP51 and it was predominantly driven by hydrophobic forces and hydrogen bonds. The present study has significant theoretical and practical implications for the development of novel 1,2,3-triazole antifungal agents.

研究领域: 植物病理学 · 药理学 · 分子生物学
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RSC Advances · 2024 ·Vol. 14 ·期 53 ·39779 · IF 3.9

Blue light-activated 5,10,15,20-tetrakis(4-bromophenyl)porphyrin for photodynamic eradication of drug-resistant Staphylococcus aureus

Hongshuang Qin,Huaying Niu,Yanxiang Guo,Xiaoting Wang,Tao Liu,Chuanqi Zhao

Photodynamic therapy (PDT) has emerged as an effective way to deal with drug-resistant bacterial infections. Especially, blue light (BL) mediated PDT (BL-PDT) presents unique advantages in the treatments of skin infection due to the strong light absorption of superficial skin, weak penetration of BL and little damage to deep tissues. However, the photosensitizers used for BL-PDT are very limited, and the ongoing development of novel BL photosensitizers is indispensable. Porphyrins are good sources for developing efficient photosensitizers. Herein, for developing more effective BL photosensitizers, five porphyrin derivatives that can be excited by BL [5,10,15,20-tetraphenylporphyrin (TPP), 5,10,15,20-tetrakis(4-bromophenyl)porphyrin (TBPP), 5,10,15,20-tetrakis(4-chlorophenyl)porphyrin (TCPP), 5,10,15,20-tetrakis(4-fluorophenyl)porphyrin (TFPP), 5,10,15,20-tetrakis(4-iodophenyl)porphyrin (TIPP)] are subjected to the investigation of PDT against MRSA (methicillin resistant Staphylococcus aureus ). The results reveal that TBPP-mediated BL-PDT shows outstanding bactericidal effects. Mechanism studies show that TBPP + BL can induce reactive oxygen species (ROS) up-regulated in MRSA, rupture cell membrane, inhibit ATP (adenosine triphosphate) production and virulence factor expression. Furthermore, TBPP + BL effectively eliminates MRSA form biofilms, inhibits biofilm formation and disintegrates mature biofilms. More importantly, TBPP-PDT significantly accelerate mouse skin wound healing in a biofilm infection model. Our work offers new insights into the development of novel BL photosensitizers. Photodynamic therapy mediated by 5,10,15,20-tetrakis(4-bromophenyl)porphyrin (TBPP) effectively eliminates drug-resistant Staphylococcus aureus , inhibits biofilm formation and accelerates wound healing in a mouse model.

CAS / MDL: 2044-85-1 4091-99-0
研究领域: 微生物学 · 药学 · 生物医学工程 · 传染病学
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