Docking, characterization and investigation of β-cyclodextrin complexed with citronellal, a monoterpene present in the essential oil of Cymbopogon species, as an anti-hyperalgesic agent in chronic muscle pain model

Santos, Priscila L.; Brito, Renan Guedes de; Oliveira, Marlange Almeida; Quintans, Jullyana S.S.; Guimarães, Adriana Gibara; Santos, Márcio Roberto Viana dos; Menezes, Irwin Rose Alencar de; Serafini, Mairim Russo; Menezes, Irwin Rose Alencar de; Coutinho, Henrique Douglas Melo; Araújo, Adriano A. S.; Quintans‐Júnior, Lucindo José

doi:10.1016/j.phymed.2016.06.007

Cited by 40 publications

(21 citation statements)

References 66 publications

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“… 21 − 23 Moreover, they can promote the controlled release of some insoluble terpenes, such as linalool, 24 limonene, 25 terpineol, 26 and citronellal. 27 …”

Section: Introductionmentioning

confidence: 99%

Methyl-β-cyclodextrin Inclusion Complex with β-Caryophyllene: Preparation, Characterization, and Improvement of Pharmacological Activities

et al. 2017

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β-Caryophyllene (BCP) is a sesquiterpene that shows high potential in pharmacological applications. However, these have been drastically limited by the respective volatility and poor water solubility. The present study investigates the formation of inclusion complexes between BCP and methyl-β-cyclodextrin (MβCD) and shows that these complexes promote a significant improvement of the anti-inflammatory, gastric protection, and antioxidant activities relative to neat BCP. It is shown that the solubility of BCP is significantly increased through complexation in phase solubility studies. Inclusion complexes with MβCD in solid state were prepared by three different methods, kneading, rotary evaporation, and lyophilization, with the latter confirmed by differential scanning calorimetry, Fourier transformed infrared spectroscopy, scanning electron microscopy, 1H NMR spectroscopy, and molecular dynamics studies. This study provides for the first time a full characterization of inclusion complexes between BCP and MβCD and highlights the impact of complex formation upon pharmacological activity.

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“… 21 − 23 Moreover, they can promote the controlled release of some insoluble terpenes, such as linalool, 24 limonene, 25 terpineol, 26 and citronellal. 27 …”

Section: Introductionmentioning

confidence: 99%

Methyl-β-cyclodextrin Inclusion Complex with β-Caryophyllene: Preparation, Characterization, and Improvement of Pharmacological Activities

et al. 2017

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“…Santos et al [30] evaluated the effect of citronellal (Figure 4), a monoterpene present in Citrus and Cymbopogon plants, complexed in β-CD as a potential agent against FM symptoms. It was observed that complexation in CD improved the anti-hyperalgesic effect when compared to noncomplexed citronellal.…”

Section: Discussion Of Unusual Topics In Fibromyalgiamentioning

confidence: 99%

“…In relation to FM, some classes of bioactive compounds extracted from medicinal plants have presented analgesic activity described in the literature, such as essential oils [24][25][26], extracts [27,28], monoterpenes [29][30][31], sesquiterpenes [32], saponins [33], and alkaloids ( Figure 1 and Table 2) [34]. * All preclinical studies used the chronic muscle pain model induced by acid saline.…”

Section: Introductionmentioning

confidence: 99%

Natural Products as Promising Pharmacological Tools for the Management of Fibromyalgia Symptoms – A Review

Brito¹,

Santos²,

AlmeidaOliveira³

et al. 2018

Discussions of Unusual Topics in Fibromyalgia

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Fibromyalgia (FM) is the second most common rheumatologic disorder, affecting 5% of the world population, and has a serious effect on the quality of life of patients, as well as an economic impact through lost workdays. This pain syndrome is a common cause of chronic widespread pain and is characterized by reduced pressure pain thresholds with hyperalgesia and allodynia, nonrestorative sleep, fatigue, cognitive dysfunction, and mood disturbances. The pharmacological treatment strategies for FM include the use of antidepressants, calcium channel modulators, muscle relaxants, and analgesics but have shown limited efficacy and therapeutic adherence. Thus, researchers have been seeking potential substances (new chemical entities or through drug repositioning) that could be used for FM treatment. In this context, natural products (NPs) have been shown to be promising pharmacological tools due to the variety of their pharmacological activity and the number of molecular sites available as possible active targets. Recent clinical and preclinical studies have been conducted to verify the possible applicability of NPs such as essential oils (EOs), plants extracts, terpenes, sapogenins, and alkaloids in the treatment of FM. The results have shown that natural products have an analgesic effect in different animal models of FM, probably by activation of inhibitory descending pathways, such as the periaqueductal gray and rostroventromedial medulla. Natural products and their secondary metabolites could therefore be a promising source for FM management. However, translational studies that seek to validate the preclinical studies are scarce, incipient, and lacking an approach focused on the traditional pharmaceutical market.

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“…Cyclodextrins are formed from the action of CD glycosyltransferase enzymes on starch, with the most important natural CDs being α, β, and γ [15]. Among the naturally occurring CDs, β-cyclodextrin (β-CD) is the one most commonly used for complexing drugs [14,[16][17][18][19] and natural products [19][20][21][22], with the aim of potentiating their pharmacological effects through increasing their stability and solubility, and making them into promising alternative treatment options.…”

Section: Introductionmentioning

confidence: 99%

Antiedematogenic and Anti-Inflammatory Activity of the Monoterpene Isopulegol and Its β-Cyclodextrin (β-CD) Inclusion Complex in Animal Inflammation Models

Ramos

Menezes

Silva

et al. 2020

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Isopulegol (ISO) is an alcoholic monoterpene widely found in different plant species, such as Melissa officinalis, and has already been reported to have a number of pharmacological properties. Like other terpenes, ISO is a highly volatile compound that is slightly soluble in water, so its inclusion into cyclodextrins (CDs) is an interesting approach to increase its solubility and bioavailability. Thus, our aim was to evaluate the antiedematogenic and anti-inflammatory activity of isopulegol and a β-cyclodextrin–isopulegol inclusion complex (ISO/β-CD) in rodent models. For the anti-inflammatory activity evaluation, antiedematogenic plethysmometry and acute (peritonitis and pleurisy), as well as chronic (cotton pellet-induced granuloma) anti-inflammatory models, were used. The docking procedure is used to evaluate, analyze, and predict their binding mode of interaction with H1 and Cox-2 receptors. The animals (n = 6) were divided into groups: ISO and ISO/β-CD, negative control (saline), and positive control (indomethacin and promethazine). ISO and ISO/β-CD were able to reduce acute inflammatory activity by decreasing albumin extravasation, leukocyte migration, and MPO concentration, and reducing exudate levels of IL-1β and TNF-α. ISO and ISO/β-CD significantly inhibited edematogenic activity in carrageenan- and dextran-induced paw edema. Moreover, both significantly reduced chronic inflammatory processes, given the lower weight and protein concentration of granulomas in the foreign body granulomatous inflammation model. The results suggest that the inclusion of ISO in β-cyclodextrins improves its pharmacological properties, with the histamine and prostaglandin pathways as probable mechanisms of inhibition, and also reinforces the anti-inflammatory profile of this terpene.

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Docking, characterization and investigation of β-cyclodextrin complexed with citronellal, a monoterpene present in the essential oil of Cymbopogon species, as an anti-hyperalgesic agent in chronic muscle pain model

Cited by 40 publications

References 66 publications

Methyl-β-cyclodextrin Inclusion Complex with β-Caryophyllene: Preparation, Characterization, and Improvement of Pharmacological Activities

Methyl-β-cyclodextrin Inclusion Complex with β-Caryophyllene: Preparation, Characterization, and Improvement of Pharmacological Activities

Natural Products as Promising Pharmacological Tools for the Management of Fibromyalgia Symptoms – A Review

Antiedematogenic and Anti-Inflammatory Activity of the Monoterpene Isopulegol and Its β-Cyclodextrin (β-CD) Inclusion Complex in Animal Inflammation Models

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