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:17
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
  • [1] An expeditious click approach towards the synthesis of galactose coated novel glyco-dendrimers and dentromers utilizing a double stage convergent method
    Agrahari, Anand K.
    Singh, Anoop S.
    Mukherjee, Rishav
    Tiwari, Vinod K.
    [J]. RSC ADVANCES, 2020, 10 (52) : 31553 - 31562
  • [2] Click inspired synthesis of hexa and octadecavalent peripheral galactosylated glycodendrimers and their possible therapeutic applications
    Agrahari, Anand K.
    Singh, Anoop S.
    Singh, Ashish Kumar
    Mishra, Nidhi
    Singh, Mala
    Prakash, Pradyot
    Tiwari, Vinod K.
    [J]. NEW JOURNAL OF CHEMISTRY, 2019, 43 (31) : 12475 - 12482
  • [3] Calixarenes and their biomimetic applications
    Agrawal, YK
    Bhatt, H
    [J]. BIOINORGANIC CHEMISTRY AND APPLICATIONS, 2004, 2 (3-4) : 237 - 274
  • [4] Calix[n]arene-based glycoclusters:: Bioactivity of thiourea-linked galactose/lactose moieties as inhibitors of binding of medically relevant lectins to a glycoprotein and cell-surface glycoconjugates and selectivity among human adhesion/growth-regulatory galectins
    Andre, Sabine
    Sansone, Francesco
    Kaltner, Herbert
    Casnati, Alessandro
    Kopitz, Juergen
    Gabius, Hans-Joachim
    Ungaro, Rocco
    [J]. CHEMBIOCHEM, 2008, 9 (10) : 1649 - 1661
  • [5] A synthetic divalent cholera toxin glycocalix[4]arene ligand having higher affinity than natural GM1 oligosaccharide
    Arosio, D
    Fontanella, M
    Baldini, L
    Mauri, L
    Bernardi, A
    Casnati, A
    Sansone, F
    Ungaro, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3660 - 3661
  • [6] Dendrimers Designed for Functions: From Physical, Photophysical, and Supramolecular Properties to Applications in Sensing, Catalysis, Molecular Electronics, Photonics, and Nanomedicine
    Astruc, Didier
    Boisselier, Elodie
    Ornelas, Catia
    [J]. CHEMICAL REVIEWS, 2010, 110 (04) : 1857 - 1959
  • [7] Peptido- and glycocalixarenes: Playing with hydrogen bonds around hydrophobic cavities
    Casnati, A
    Sansone, F
    Ungaro, R
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) : 246 - 254
  • [8] Achieving High Affinity towards a Bacterial Lectin through Multivalent Topological Isomers of Calix[4]arene Glycoconjugates
    Cecioni, Samy
    Lalor, Ruth
    Blanchard, Bertrand
    Praly, Jean-Pierre
    Imberty, Anne
    Matthews, Susan E.
    Vidal, Sebastien
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (47) : 13232 - 13240
  • [9] Topomimetics of amphipathic β-sheet and helix-forming bactericidal peptides neutralize lipopolysaccharide endotoxins
    Chen, Xuemei
    Dings, Ruud P. M.
    Nesmelova, Irina
    Debbert, Stefan
    Haseman, Judith R.
    Maxwell, Jacques
    Hoye, Thomas R.
    Mayo, Kevin H.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (26) : 7754 - 7765
  • [10] A series of potent and selective, triazolylphenyl-based histone deacetylases inhibitors with activity against pancreatic cancer cells and Plasmodium falciparum
    Chen, Yufeng
    Lopez-Sanchez, Miriam
    Savoy, Doris N.
    Billadeau, Daniel D.
    Dow, Geoffrey S.
    Kozikowski, Alan P.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (12) : 3437 - 3448