Anti-inflammatory effect of photodynamic therapy using guaiazulene and red lasers on peripheral blood mononuclear cells

Phutim-Mangkhalthon, Ampika; Teerakapong, Aroon; Tippayawat, Patcharaporn; Morales, Noppawan Phumala; Morkmued, Supawich; Puasiri, Subin; Priprem, Aroonsri; Damrongrungruang, Teerasak

doi:10.1016/j.pdpdt.2020.101747

Cited by 18 publications

(16 citation statements)

References 57 publications

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“…Azulene moiety, as an element of molecular consortia, raises great hope for effective anticancer drugs. Photodynamic activation with red laser light and guaiazulene revealed the generation of singlet oxygen and suppression of inflammatory markers in peripheral blood mononuclear cells [53]. The chamazulene/camphor-rich essential oils containing 63% of chamazulene from Artemisia arborescens plants collected in Sicily showed promising activity on studied melanoma cancer cells with potential to trigger apoptotic death [54].…”

Section: Antineoplastic Activitymentioning

confidence: 99%

In vitro and in vivo biological activities of azulene derivatives with potential applications in medicine

Bakun

Czarczyńska-Goślińska

Gośliński

et al. 2021

Med Chem Res

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Azulene is an aromatic hydrocarbon that possesses a unique chemical structure and interesting biological properties. Azulene derivatives, including guaiazulene or chamazulene, occur in nature as components of many plants and mushrooms, such as Matricaria chamomilla, Artemisia absinthium, Achillea millefolium, and Lactarius indigo. Due to physicochemical properties, azulene and its derivatives have found many potential applications in technology, especially in optoelectronic devices. In medicine, the ingredients of these plants have been widely used for hundreds of years in antiallergic, antibacterial, and anti-inflammatory therapies. Herein, the applications of azulene, its derivatives and their conjugates with biologically active compounds are presented. The potential use of these compounds concerns various areas of medicine, including anti-inflammatory with peptic ulcers, antineoplastic with leukemia, antidiabetes, antiretroviral with HIV-1, antimicrobial, including antimicrobial photodynamic therapy, and antifungal.

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Section: Antineoplastic Activitymentioning

confidence: 99%

In vitro and in vivo biological activities of azulene derivatives with potential applications in medicine

Bakun

Czarczyńska-Goślińska

Gośliński

et al. 2021

Med Chem Res

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“…The present study demonstrated that among twelve guaiazulene-3-carboxylates, two alkoxyl guaiazulene-3carboxylates [6,7] showed higher tumor-specificity than five alkyl [1][2][3][4][5] and two hydroxyalkyl [8,9] guaiazulene-3carboxylates and three aminoalkyl guaiazulene-3-carboxylate carboxamides [10][11][12] (Table I). Both [6,7] showed higher TS value than CDDP and CBDCA, and having comparable PSE value with 5-FU (Table I).…”

Section: Discussionmentioning

confidence: 97%

“…[9], 2-aminoethyl guaiazulene-3-carboxylate [10], 3-aminoprpyl guaiazulene-3-carboxylate [11], 4-aminobutyl guaiazulene-3carboxylate [12] ( Figure 1G) were synthesized, according to previous reports (6,17,18). N-(2-methoxyethyl)guaiazulenecarboxamide [X] was synthesized as previously described (15).…”

Section: Figure 1 Structure Of Azulene (A) Guaiazulene (B) Alkylammentioning

confidence: 99%

“…We have repeated the same experiments 3 times. The mean values of CC 50 , tumor-selectivity index (TS), and potency-selectivity expression (PSE) of these twelve compounds, as well as of positive controls (5-FU, CDDP, and CBDCA) obtained from these 3 independent experiments are listed in PSE=13.0±1.9) showed the highest TS values than five alkyl guaiazulene-3-carboxylates [1][2][3][4][5], two hydroxyalkyl guaiazulene-3-carboxylates [8,9], and three aminoalkyl guaiazulene-3-carboxylates [10][11][12] (Table I). Moreover, both [6,7] showed higher TS value than CDDP and CBDCA (TS mean =2.2±1.5 and 2.4±1.1, respectively), and had PSE (mean) values comparable to that of 5-FU (13.4±6.5).…”

Section: Calculation Of Potency-selectivity Expression (Pse)mentioning

confidence: 99%

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Antitumor Effects and Tumor-specificity of Guaiazulene-3-Carboxylate Derivatives Against Oral Squamous Cell CarcinomaIn Vitro

et al. 2020

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Aim: The aim of this study was to investigate the antitumor potential of guaiazulene-3-carboxylate derivatives against oral malignant cells. Materials and Methods: Twelve guaiazulene-3-carboxylate derivatives were synthesized by introduction of either with alkyl group [1-5], alkoxy group [6, 7], hydroxyl group [8, 9] or primary amine [10-12] at the end of sidechains. Tumor-specificity (TS) was calculated by the ratio of mean 50% cytotoxic concentration (CC 50) against 3 human oral mesenchymal cell lines to that against 4 human oral squamous cell carcinoma (OSCC) cell lines. Potencyselectivity expression (PSE) was calculated by dividing TS value by CC 50 value against OSCC cell lines. Cell cycle analysis was performed by cell sorter. Results: [6, 7] showed the highest TS and PSE values, and induced the accumulation of both subG 1 and G 2 /M cell populations in HSC-2 OSCC cells. Quantitative structure-activity relationship analysis demonstrated that their tumor-specificity was correlated with chemical descriptors that explain the 3D shape, electric state and ionization potential. Conclusion: Alkoxyl guaiazulene-3carboxylates [6, 7] can be potential candidates of lead compound for developing novel anticancer drugs.

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“…therapeutic effect on various types of inflammation, widely known empirically. The anti-inflammatory effect is suggested to be due to the presence of azulene in the essential oil component of chamomile leachate [15] [16].…”

Section: Accepted Articlementioning

confidence: 99%

Guaiazulene derivative 1,2,3,4‐tetrahydroazuleno[1,2‐b] tropone reduces the production of ATP by inhibiting electron transfer complex II

2021

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Molecularly targeted therapy has been employed for treatment of various types of cancers. However, cancer cells often acquire resistance to molecularly targeted drugs that inhibit specific molecular abnormalities, such as constitutive activation of kinases. Even in cancer cells that have acquired resistance, enhanced anabolism, including the synthesis of nucleotides, amino acids, and lipids, is common to normal cancer cells. Therefore, there is a renewed interest in effectively eliminating cancer cells by specifically targeting their abnormal energy metabolism. Multiple strategies are currently being developed for mitochondrial-targeted cancer therapy, with agents targeting oxidative phosphorylation, glycolysis, the tricarboxylic acid cycle, and apoptosis. In this study, we found that one of the guaiazulene derivatives, namely 1,2,3,4-tetrahydroazuleno[1,2-b] tropone (TAT), inhibited the proliferation of cancer cell lines stronger than that of normal cells. Additionally, we showed that TAT inhibited energy production in cancer cell lines, resulting in apoptosis. Analyses done in cancer cell lines

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Anti-inflammatory effect of photodynamic therapy using guaiazulene and red lasers on peripheral blood mononuclear cells

Cited by 18 publications

References 57 publications

In vitro and in vivo biological activities of azulene derivatives with potential applications in medicine

In vitro and in vivo biological activities of azulene derivatives with potential applications in medicine

Antitumor Effects and Tumor-specificity of Guaiazulene-3-Carboxylate Derivatives Against Oral Squamous Cell CarcinomaIn Vitro

Guaiazulene derivative 1,2,3,4‐tetrahydroazuleno[1,2‐b] tropone reduces the production of ATP by inhibiting electron transfer complex II

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