Novel Cationic Quinazolin-4(3H)-one Conjugated Fullerene Nanoparticles as Antimycobacterial and Antimicrobial Agents

被引:23
作者
Patel, Manishkumar B. [1 ]
Harikrishnan, Uma [1 ]
Valand, Nikunj N. [1 ]
Modi, Nishith R. [1 ]
Menon, Shobhana K. [1 ]
机构
[1] Gujarat Univ, Sch Sci, Dept Chem, Ahmadabad 380009, Gujarat, India
关键词
Antibacterial study; Antifungal study; Antimycobacterial study; Cationic fulleropyrrolidines; Quinazolin-4(3H)-one; BIOLOGICAL EVALUATION; C-60; DERIVATIVES; MYCOBACTERIA; DESIGN; DRUG;
D O I
10.1002/ardp.201200371
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of novel cationic fullerene derivatives bearing a substituted-quinazolin-4(3H)-one moiety as a side arm were synthesized using the 1,3-dipolar cycloaddition reaction of C60 with azomethine ylides generated from the corresponding Schiff bases of substituted quinazolinones. The synthesized compounds 5af were characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, and ESI-MS and screened for their antibacterial activity against Mycobacterium tuberculosis (H37RV) and antimicrobial activity against selected Gram-positive (Staphylococcus aureus and S. pyogenes) and Gram-negative (Pseudomonas aeruginosa, Klebsiella pneumonia and Escherichia coli) bacterial and fungal strains (Candida albicans, Aspergillus clavatus, and A. niger), respectively. All the compounds exhibited significant activity, with the most effective compounds having MIC values and zones of inhibition comparable to those of standard drugs.
引用
收藏
页码:210 / 220
页数:11
相关论文
共 28 条
  • [11] C-60 - BUCKMINSTERFULLERENE
    KROTO, HW
    HEATH, JR
    OBRIEN, SC
    CURL, RF
    SMALLEY, RE
    [J]. NATURE, 1985, 318 (6042) : 162 - 163
  • [12] Potentiometric Biosensing of Glucose by Fullerene-Based Silver Selective Electrodes
    Kumar, Anish
    Patel, Bhargav
    Patel, Gaurang
    Menon, Shobhana K.
    [J]. FULLERENES NANOTUBES AND CARBON NANOSTRUCTURES, 2010, 18 (03) : 186 - 197
  • [13] Photoinduced DNA cleavage by fullerene-lysine conjugate
    Kumar, Anish
    Rao, Mandava V.
    Menon, Shobhana K.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (47) : 6526 - 6530
  • [14] Fullerene-ferrocene dyad linked by rigid bilinkage: synthesis, photophysical properties and application as copper ion sensor
    Kumar, Anish
    Menon, Shobhana K.
    [J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2009, 22 (07) : 661 - 669
  • [15] Fullerene Isoniazid Conjugate - A Tuberculostat with Increased Lipophilicity: Synthesis and Evaluation of Antimycobacterial Activity
    Kumar, Anish
    Patel, Gaurang
    Menon, Shobhana Karuveettil
    [J]. CHEMICAL BIOLOGY & DRUG DESIGN, 2009, 73 (05) : 553 - 557
  • [16] Cellular impermeability and uptake of biocides and antibiotics in Gram-positive bacteria and mycobacteria
    Lambert, PA
    [J]. JOURNAL OF APPLIED MICROBIOLOGY, 2002, 92 : 46S - 54S
  • [17] Materials chemistry of fullerene C60 derivatives
    Lopez, Alejandro Montellano
    Mateo-Alonso, Aurelio
    Prato, Maurizio
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (05) : 1305 - 1318
  • [18] Antibacterial activity of fullerene water suspensions: Effects of preparation method and particle size
    Lyon, Delina Y.
    Adams, Laura K.
    Falkner, Joshua C.
    Alvarez, Pedro J. J.
    [J]. ENVIRONMENTAL SCIENCE & TECHNOLOGY, 2006, 40 (14) : 4360 - 4366
  • [19] ADDITION OF AZOMETHINE YLIDES TO C-60 - SYNTHESIS, CHARACTERIZATION, AND FUNCTIONALIZATION OF FULLERENE PYRROLIDINES
    MAGGINI, M
    SCORRANO, G
    PRATO, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) : 9798 - 9799
  • [20] Design, Synthesis & Biological Evaluation of Some Novel Quinazolinone Scaffolds
    Modh, Rahul P.
    Patel, Amit C.
    Chikhalia, Kishor H.
    [J]. MEDICINAL CHEMISTRY, 2012, 8 (02) : 182 - 192