Synthesis and antituberculosis activity of new fatty acid amides

被引：57
作者：
Montes D'Oca, Caroline Da Ros [1 ]
Coelho, Tatiane [2 ]
Marinho, Tamara Germani [1 ]
Lopes Hack, Carolina Rosa [1 ]
Duarte, Rodrigo da Costa [1 ]
da Silva, Pedro Almeida [2 ]
Montes D'Oca, Marcelo Goncalves [1 ]
机构：
[1] Univ Fed Rio Grande, Escola Quim & Alimentos, Lab Kolbe Sintese Organ, Rio Grande, RS, Brazil
[2] Univ Fed Rio Grande, Fac Med, Lab Micobacteriol, Rio Grande, RS, Brazil
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 17期
关键词：
Mycobacterium tuberculosis; Fatty acid amides; Ricinoleic acid; FAMEs; ENDOCANNABINOID SYSTEM; MYCOBACTERIUM-TUBERCULOSIS; ANANDAMIDE; OLEAMIDE; CANCER; TARGET;
D O I：
10.1016/j.bmcl.2010.06.149
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
This work reports the synthesis of new fatty acid amides from C16: 0, 18: 0, 18: 1, 18: 1 (OH), and 18: 2 fatty acids families with cyclic and acyclic amines and demonstrate for the first time the activity of these compounds as antituberculosis agents against Mycobacterium tuberculosis H(37)Rv, M. tuberculosis rifampicin resistance (ATCC 35338), and M. tuberculosis isoniazid resistance (ATCC 35822). The fatty acid amides derivate from ricinoleic acid were the most potent one among a series of tested compounds, with a MIC 6.25 mu g/mL for resistance strains. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5255 / 5257
页数：3
相关论文
共 23 条
  • [1] Inhibitory effect of the anorexic compound oleoylethanolamide on gastric emptying in control and overweight mice
    Aviello, Gabriella
    Matias, Isabel
    Capasso, Raffaele
    Petrosino, Stefania
    Borrelli, Francesca
    Orlando, Pierangelo
    Romano, Barbara
    Capasso, Francesco
    Di Marzo, Vincenzo
    Izzo, Angelo A.
    [J]. JOURNAL OF MOLECULAR MEDICINE-JMM, 2008, 86 (04): : 413 - 422
  • [2] Anandamide - A new look on fatty acid ethanolamides
    Berdyshev, EV
    Boichot, E
    Lagente, V
    [J]. JOURNAL OF LIPID MEDIATORS AND CELL SIGNALLING, 1996, 15 (01): : 49 - 67
  • [3] Chemical requirements for inhibition of gap junction communication by the biologically active lipid oleamide
    Boger, DL
    Patterson, JE
    Guan, XJ
    Cravatt, BF
    Lerner, RA
    Gilula, NB
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (09) : 4810 - 4815
  • [4] Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation
    Burstein, Sumner
    Salmonsen, Rebecca
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (22) : 9644 - 9651
  • [5] The Mycobacterium tuberculosis iniA gene is essential for activity of an efflux pump that confers drug tolerance to both isoniazid and ethambutol
    Colangeli, R
    Helb, D
    Sridharan, S
    Sun, JC
    Varma-Basil, M
    Hazbón, MH
    Harbacheuski, R
    Megjugorac, NJ
    Jacobs, WR
    Holzenburg, A
    Sacchettini, JC
    Alland, D
    [J]. MOLECULAR MICROBIOLOGY, 2005, 55 (06) : 1829 - 1840
  • [6] Di Marzo V, 1999, CURR MED CHEM, V6, P721
  • [7] Targeting the endocannabinoid system: to enhance or reduce?
    Di Marzo, Vincenzo
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2008, 7 (05) : 438 - 455
  • [8] Oleamide synthesizing activity from rat kidney - Identification as cytochrome C
    Driscoll, William J.
    Chaturvedi, Shalini
    Mueller, Gregory P.
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2007, 282 (31) : 22353 - 22363
  • [9] Biosynthesis, degradation and pharmacological importance of the fatty acid amides
    Farrell, Emma K.
    Merkler, David J.
    [J]. DRUG DISCOVERY TODAY, 2008, 13 (13-14) : 558 - 568
  • [10] The endocannabinoid system in cancer - Potential therapeutic target?
    Flygare, Jenny
    Sander, Birgitta
    [J]. SEMINARS IN CANCER BIOLOGY, 2008, 18 (03) : 176 - 189
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