Click inspired synthesis of p-tert-butyl calix[4]arene tethered benzotriazolyl dendrimers and their evaluation as anti-bacterial and anti-biofilm agents

被引:19
作者
Agrahari, Anand K. [1 ]
Singh, Ashish K. [2 ]
Singh, Anoop S. [1 ]
Singh, Mala [1 ]
Maji, Pathik [3 ]
Yadav, Shivangi [2 ]
Rajkhowa, Sanchayita [4 ]
Prakash, Pradyot [2 ]
Tiwari, Vinod K. [1 ]
机构
[1] Banaras Hindu Univ, Ctr Adv Study, Inst Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
[2] Banaras Hindu Univ, Inst Med Sci, Dept Microbiol, Bacterial Biofilm & Drug Resistance Res Lab, Varanasi 221005, Uttar Pradesh, India
[3] Guru Ghasidas Univ, Dept Chem, Bilaspur 495009, India
[4] Jorhat Inst Sci & Technol, Dept Chem, Jorhat 785010, Assam, India
关键词
BIOLOGICAL APPLICATIONS; CALIXARENE; CHEMISTRY; TRIAZOLE; INHIBITORS; NANOPARTICLES; CYCLOADDITION; CYTOTOXICITY; DERIVATIVES; SELECTIVITY;
D O I
10.1039/d0nj02591g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Calixarenes with their three-dimensional structural architecture and ease of functionalization at the upper and/or lower rim are well-known for their plethora of applications in chemical, physical, biological and other disciplines. Herein, CuAAC click inspired p-tert-butylcalix[4]arene tethered benzotriazolyl dendrimers, for example, N-1, N-2 type 2-fold compound 6 and 7 'G(0)' and 6-fold compound 16 and 17 'G(1)' generation benzotriazolyl dendrimer, were devised and also evaluated for their therapeutic potential both in vitro and in vivo. The developed calix[4]arene tethered benzotriazolyl dendrimers have been characterized by standard spectroscopic analysis including NMR (H-1 and C-13), MS, and SEC. Among all the benzotriazolyl dendrimers developed, compound 7 was identified as the effective one which provided potential anti-bacterial and anti-biofilm activities against drug-resistant and slime producing organisms without imparting cytotoxicity to the eukaryotic systems.
引用
收藏
页码:19300 / 19313
页数:14
相关论文
共 84 条
[21]   Calix[4]arene decorated with four tn antigen glycomimetic units and P3CS immunoadjuvant:: Synthesis, characterization, and anticancer immunological evaluation [J].
Geraci, Corrada ;
Consoli, Grazia M. L. ;
Galante, Eva ;
Bousquet, Ennio ;
Pappalardo, Maria ;
Spadaro, Angelo .
BIOCONJUGATE CHEMISTRY, 2008, 19 (03) :751-758
[22]  
Gerald C. J., 1996, MACKIE MCCARTNEY PRA, P151
[23]   Curcumin is a modulator of bilayer material properties [J].
Ingolfsson, Helgi I. ;
Koeppe, Roger E., II ;
Andersen, Olaf S. .
BIOCHEMISTRY, 2007, 46 (36) :10384-10391
[24]   Synthesis and antimicrobial potential of nitrofuran-triazole congeners [J].
Kamal, Ahmed ;
Hussaini, S. M. Ali ;
Sucharitha, M. Lakshmi ;
Poornachandra, Y. ;
Sultana, Faria ;
Kumar, C. Ganesh .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (36) :9388-9397
[25]   Synthesis of Heterocycles Mediated by Benzotriazole. 1. Monocyclic Systems [J].
Katritzky, Alan R. ;
Rachwal, Stanislaw .
CHEMICAL REVIEWS, 2010, 110 (03) :1564-1610
[26]   Efficient conversion of carboxylic acids into N-acylbenzotriazoles [J].
Katritzky, AR ;
Zhang, YM ;
Singh, SK .
SYNTHESIS-STUTTGART, 2003, (18) :2795-2798
[27]   Properties and synthetic utility of N-substituted benzotriazoles [J].
Katritzky, AR ;
Lan, XF ;
Yang, JZ ;
Denisko, OV .
CHEMICAL REVIEWS, 1998, 98 (02) :409-548
[28]   The growing impact of click chemistry on drug discovery [J].
Kolb, HC ;
Sharpless, KB .
DRUG DISCOVERY TODAY, 2003, 8 (24) :1128-1137
[29]   Synthesis of 2-N/S/C-Substituted Benzothiazoles via Intramolecular Cyclative Cleavage of Benzotriazole Ring [J].
Kumar, Dhananjay ;
Mishra, Bhuwan B. ;
Tiwari, Vinod K. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (01) :251-266
[30]  
Kumar SS, 2013, MINI-REV ORG CHEM, V10, P40