Antimicrobial evaluation and action mechanism of pyridinium-decorated l,4-pentadien-3-one derivatives

被引:43
作者
Zhou, Jian [1 ]
Tao, Qing-Qing [1 ]
Wang, Pei-Yi [1 ]
Shao, Wu-Bin [1 ]
Wu, Zhi-Bing [1 ]
Li, Zhong [2 ]
Yang, Song [1 ,2 ]
机构
[1] Guizhou Univ, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn, Minist Educ,Ctr R&D Fine Chem, Guiyang 550025, Guizhou, Peoples R China
[2] East China Univ Sci & Technol, Coll Pharm, Shanghai 550025, Peoples R China
基金
中国国家自然科学基金;
关键词
Pyridinium; 1,4-Pentadien-3-one; Synthesis; Action mechanism; Antimicrobial; BACTERIAL LEAF-BLIGHT; ORYZAE PV. ORYZAE; ANTIBACTERIAL ACTIVITY; ANTIVIRAL ACTIVITY; 1,4-PENTADIEN-3-ONE DERIVATIVES; BIOLOGICAL EVALUATION; ANTIFUNGAL ACTIVITY; CURCUMIN; MOIETY; RICE;
D O I
10.1016/j.bmcl.2018.04.034
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A type of pyridinium-decorated l,4-pentadien-3-one derivatives possessing flexible alkyls were designed and synthesized by integrating the key scaffolds of pyridinium cations and l,4-pentadien-3-one skeleton in a single molecular architecture. Antimicrobial bioassays indicated that some of the target molecules exerted considerable bioactivities against six phytopathogenic strains, especially for Xanthomonas oryzae pv. oryzae, the minimal EC50 value can reach to 0.504 mu g/mL. A plausible action mechanism for this land of compounds was proposed and confirmed by employing fluorescent spectroscopy, fluorescence microscopy, and scanning electron microscopy. We anticipated that this finding can promote high-efficient lead compounds discovery in the research of antimicrobial chemotherapy. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1742 / 1746
页数:5
相关论文
共 38 条
[1]   Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents [J].
Adams, BK ;
Ferstl, EM ;
Davis, MC ;
Herold, M ;
Kurtkaya, S ;
Camalier, RF ;
Hollingshead, MG ;
Kaur, G ;
Sausville, EA ;
Rickles, FR ;
Snyder, JP ;
Liotta, DC ;
Shoji, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (14) :3871-3883
[2]   Curcumin: An Anti-Inflammatory Molecule from a Curry Spice on the Path to Cancer Treatment [J].
Basnet, Purusotam ;
Skalko-Basnet, Natasa .
MOLECULES, 2011, 16 (06) :4567-4598
[3]   Curcumin Recognizes a Unique Binding Site of Tubulin [J].
Chakraborti, Soumyananda ;
Das, Lalita ;
Kapoor, Neha ;
Das, Amlan ;
Dwivedi, Vishnu ;
Poddar, Asim ;
Chakraborti, Gopal ;
Janik, Mark ;
Basu, Gautam ;
Panda, Dulal ;
Chakrabarti, Pinak ;
Surolia, Avadhesha ;
Bhattacharyya, Bhabatarak .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (18) :6183-6196
[4]   Synthesis, structure and in vitro antibacterial activities of new hybrid disinfectants quaternary ammonium compounds: Pyridinium and quinolinium stilbene benzenesulfonates [J].
Chanawanno, Kullapa ;
Chantrapromma, Suchada ;
Anantapong, Theerasak ;
Kanjana-Opas, Akkharawit ;
Fun, Hoong-Kun .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) :4199-4208
[5]   Antifungal activity of 4-methyl-6-alkyl-2H-pyran-2-ones [J].
Chattapadhyay, TK ;
Dureja, P .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (06) :2129-2133
[6]  
Chattopadhyay I, 2004, CURR SCI INDIA, V87, P44
[7]   Activity of a novel bactericide, zinc thiazole against Xanthomonas oryzae pv. oryzae in Anhui Province of China [J].
Chen, Y. ;
Yang, X. ;
Gu, C-Y. ;
Zhang, A-F. ;
Zhang, Y. ;
Wang, W-X. ;
Gao, T-C. ;
Yao, J. ;
Yuan, S-K. .
ANNALS OF APPLIED BIOLOGY, 2015, 166 (01) :129-135
[8]   The structure of the lipooligosaccharide from Xanthomonas oryzae pv. Oryzae: the causal agent of the bacterial leaf blight in rice [J].
Di Lorenzo, Flaviana ;
Palmigiano, Angelo ;
Silipo, Alba ;
Desaki, Yoshitake ;
Garozzo, Domenico ;
Lanzetta, Rosa ;
Shibuya, Naoto ;
Molinaro, Antonio .
CARBOHYDRATE RESEARCH, 2016, 427 :38-43
[9]   Biologic evaluation of curcumin and structural derivatives in cancer chemoprevention model systems [J].
Gafner, S ;
Lee, SK ;
Cuendet, M ;
Barthélémy, S ;
Vergnes, L ;
Labidalle, S ;
Mehta, RG ;
Boone, CW ;
Pezzuto, JM .
PHYTOCHEMISTRY, 2004, 65 (21) :2849-2859
[10]   Design, synthesis, antiviral activity and three-dimensional quantitative structure-activity relationship study of novel 1,4-pentadien-3-one derivatives containing the 1,3,4-oxadiazole moiety [J].
Gan, Xiuhai ;
Hu, Deyu ;
Li, Pei ;
Wu, Jian ;
Chen, Xuewen ;
Xue, Wei ;
Song, Baoan .
PEST MANAGEMENT SCIENCE, 2016, 72 (03) :534-543