TRP and ASIC channels mediate the antinociceptive effect of citronellyl acetate

Rios, Emiliano Ricardo Vasconcelos; Rocha, Nayrton Flávio Moura; Carvalho, Alyne Mara Rodrigues de; Vasconcelos, Leonardo Freire; Dias, Marília Leite; Sousa, Damião Pergentino de; Sousa, Francisca Cléa Florenço de; Fonteles, Marta Maria de França

doi:10.1016/j.cbi.2013.03.014

Cited by 34 publications

(15 citation statements)

References 45 publications

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“…This might in part explain the lack of efficacy of SB-366791, capsazepine, and AMTB in our study, in which a relatively high concentration of formalin (5%) was used. Moreover, it must be emphasized that formalin-induced pain involves numerous mediators, channels, and receptors (Santos and Calixto, 1997;Coste et al, 2012), as well as nerve fiber types (Rios et al, 2013) and signaling pathways (Coste et al, 2012), so a selective inhibition of only one type of TRP channels might be insufficient to obtain effective antinociception. In addition, the local administration of TRP channel antagonists used in our study, and hence their strictly peripheral, local action might explain the lack of efficacy observed in the second phase of the test during which central sensitization of pain plays a pivotal role.…”

Section: Discussionmentioning

confidence: 99%

“…In contrast to this, nociception evoked by formalin and paclitaxel is not so clearly understood as it involves several distinct mechanisms. It was previously shown that formalin-induced pain is evoked by the activity of numerous mediators, channels, and receptors (Santos and Calixto, 1997;Coste et al, 2012), as well as nerve fiber types (Rios et al, 2013) and signaling pathways (Coste et al, 2012). Paclitaxel in turn is a chemotherapeutic agent, which causes toxic painful neuropathy and pain that are usually resistant to analgesic drugs (Nieto et al, 2012;Hara et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

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Antinociceptive activity of transient receptor potential channel TRPV1, TRPA1, and TRPM8 antagonists in neurogenic and neuropathic pain models in mice

Sałat

Filipek

2015

J. Zhejiang Univ. Sci. B

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Abstract:The aim of this research was to assess the antinociceptive activity of the transient receptor potential (TRP) channel TRPV1, TRPM8, and TRPA1 antagonists in neurogenic, tonic, and neuropathic pain models in mice. For this purpose, TRP channel antagonists were administered into the dorsal surface of a hind paw 15 min before capsaicin, allyl isothiocyanate (AITC), or formalin. Their antiallodynic and antihyperalgesic efficacies after intraperitoneal administration were also assessed in a paclitaxel-induced neuropathic pain model. Motor coordination of paclitaxeltreated mice that received these TRP channel antagonists was investigated using the rotarod test. TRPV1 antagonists, capsazepine and SB-366791, attenuated capsaicin-induced nociceptive reaction in a concentration-dependent manner. At 8 µg/20 µl, this effect was 51% (P<0.001) for capsazepine and 37% (P<0.05) for SB-366791. A TRPA1 antagonist, A-967079, reduced pain reaction by 48% (P<0.05) in the AITC test and by 54% (P<0.001) in the early phase of the formalin test. The test compounds had no influence on the late phase of the formalin test. In paclitaxel-treated mice, they did not attenuate heat hyperalgesia but N-(3-aminopropyl)-2-{ [(3-methylphenyl)methyl]oxy}-N-(2-thienylmethyl) benzamide hydrochloride salt (AMTB), a TRPM8 antagonist, reduced cold hyperalgesia and tactile allodynia by 31% (P<0.05) and 51% (P<0.01), respectively. HC-030031, a TRPA1 channel antagonist, attenuated tactile allodynia in the von Frey test (62%; P<0.001). In conclusion, distinct members of TRP channel family are involved in different pain models in mice. Antagonists of TRP channels attenuate nocifensive responses of neurogenic, tonic, and neuropathic pain, but their efficacies strongly depend on the pain model used.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antinociceptive activity of transient receptor potential channel TRPV1, TRPA1, and TRPM8 antagonists in neurogenic and neuropathic pain models in mice

Sałat

Filipek

2015

J. Zhejiang Univ. Sci. B

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“…The odor of citronellol has previously been described as being sweet, rose-like (Hognadottir & Rouseff, 2003;Zhao et al, 2016), while citronellyl acetate, 2, has been reported to elicit a fresh, fruity smell associated with a lemon scent (Zhao et al, 2016). Due to their pleasant smell properties, 1 and 2 are fragrant compounds that are widely used in perfumes with citrus, floral notes (Bartsch, Uhde, & Salthammer, 2016;Rios et al, 2013). Owing to the chiral center at carbon 3, b-citronellol has two isomeric forms that both occur in nature.…”

Section: Introductionmentioning

confidence: 97%

“…2 is also present as major constituent in Corymbia citriodora (Rios et al, 2013). This plant, also known as Eucalyptus citriodora resin, has been demonstrated to be a potent antihepatoma agent with pro-apoptotic activity in HepG2 cells (human hepatoma cells); moreover, it also exerts antifungal, antibacterial and insect-repellent activity (Shen, Chen, & Duh, 2012).…”

Section: Introductionmentioning

confidence: 98%

Influence of the chemical structure on the odor characters of β-citronellol and its oxygenated derivatives

Elsharif

Buettner

2017

Food Chemistry

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“…polyurethanes), and protect groups in organic synthesis [15][16][17][18]. N-methyl terpinyl carbamates are biologically active compounds due to their molluscicidal effect [19].…”

Section: Introductionmentioning

confidence: 99%

Tin-Catalyzed Urea Alcoholysis With β-Citronellol: A Simple and Selective Synthesis of Carbamates

Chaves

Silva

2016

Catal Lett

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Tin(II) chloride is a stable and water tolerant Lewis acid, commercially available and less corrosive than Brønsted acid catalysts. Our proposal was demonstrated that SnCl 2 was an efficient catalyst on the urea alcoholysis with b-citronellol. We investigated the effects of main reaction parameters such as concentration and tin(II) catalyst nature, reagents stoichiometry and reaction temperature. In homogenous conditions with DMSO as solvent, the SnCl 2 -catalyzed urea alcoholysis reactions under air flux achieved high conversion and selectivity for b-citronellyl carbamate (ca. 90 and 95 %, respectively). Among tin(II) catalysts assessed, SnCl 2 was more active due to its total solubility. Possible intermediates of active Sn(II) species were discussed based on the results of catalytic runs and FT-IR spectroscopy measurements of the liquid phase after the reaction. FT-IR spectroscopy data showed that the active species could be a complex of a Sn(II) atom coordinated with N=C=O. This novel and phosgene-free selective process provide an inexpensive and attractive route to synthesize terpenic carbamates through inexpensive and renewable reactant (i.e. urea). Moreover, SnCl 2 was also an efficient catalyst on synthesis of b-citronellyl carbonate. Graphical AbstractOH -citronellol H 2 N NH 2 O Urea + SnCl 2 DMSO Air flow O NH 2 O -citronellyl Carbamate NH 3 + Ammonia β 0 3 0 6 0 9 0 0 20 40 60 80 100 (%) Time (min) β -Citronellol Conversion Selectivity β-Citronellyl Carbamate β

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TRP and ASIC channels mediate the antinociceptive effect of citronellyl acetate

Abstract: The results of this work contribute information regarding the antinociceptive properties of CAT on acute pain and show that, at least in part, TRPV1, TRPM8, ASIC, glutamate receptors, PKC and PKA participate in CAT's antinociceptive mechanism.

Cited by 34 publications

References 45 publications

Antinociceptive activity of transient receptor potential channel TRPV1, TRPA1, and TRPM8 antagonists in neurogenic and neuropathic pain models in mice

Antinociceptive activity of transient receptor potential channel TRPV1, TRPA1, and TRPM8 antagonists in neurogenic and neuropathic pain models in mice

Influence of the chemical structure on the odor characters of β-citronellol and its oxygenated derivatives

Tin-Catalyzed Urea Alcoholysis With β-Citronellol: A Simple and Selective Synthesis of Carbamates

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