Synthesis of novel (-)-Camphene-based thiosemicarbazones and evaluation of anti-<i>Mycobacterium tuberculosis</i> activity

Souza, Mariana Regina Passos de; Coelho, Narcimário Pereira; Baldin, Vanessa Pietrowski; Scodro, Regiane Bertin de Lima; Cardoso, Rosilene Fressatti; Silva, Cleuza C. da; Vandresen, Fábio

doi:10.1080/14786419.2018.1478829

Cited by 23 publications

(20 citation statements)

References 21 publications

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“…Chemical Composition of Ginger Essential Oil (Zingiber officinale) Analyzed by Gas chromatography n, number of alkane carbons eluting before "i"; m, number of alkane carbons eluting after "i"; Dn, "m"-"n"; tri, retention time of i (sample); trn, retention time of standard "n" (standard before); trm, retention time of pattern "m" (pattern after); IKA, 100*n + 100*Dn* (trA-trn/trm-trn); %, Percent of the compound. Among the most important compounds present in our GEO sample, the monoterpenes citral, δ-citral and camphene show important pharmacological properties, including antioxidant, analgesic and antitumor activity (Souza et al, 2018). Our results are comparable to the literature results where the most significant phytochemical components found corroborate the study of Höferl et al, (2015), varying only the percentages (citral -10.5%; camphene -7.8%; α-zingiberene -17.4%).…”

Section: Discussionsupporting

confidence: 89%

Evaluation of Antineoplasic Activity of Zingiber Officinale Essential Oil in the Colorectal Region of Wistar Rats

Lima

Pelegrini

Uechi

et al. 2020

Asian Pac J Cancer Prev

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Introduction: Aberrant Crypt (AC) and Aberrant Crypt Focus (ACF) are considered pre-neoplasic lesions, ranging from hyperplasia to different degrees of dysplasia in the colon. This work aimed to evaluate and quantify the chemopreventive activity of Zingiber officinale essential oil in the colorectal region of Wistar rats. Materials and Methods: We extracted the essential oil from ginger rhizomes and carried out ACF induction, in rats, with 1.2 Dimethylhydrazine (DMH) at a 20 mg/kg dose. The experimental groups were GI (negative control); GII (positive induction control); GIII (DMH + essential oil); GIV (DMH +5-Florouracil) and GV (essential oil). The histological techniques used were methylene blue, hematoxylin-eosin (HE) dyeing, and immunohistochemistry (IHQ). Results: The major essential oil compounds were citral (17.25%), δ-citral (10.25%), camphene (9.55%), α-zingiberene (7.57%), nerol (6.37%) and plelandrene (6.83%). For the presence of AC or ACF, we did not observe them in GI and GV, while in GII and GIII, they were observed, in high values, in both regions, but only in the distal region, there was a significant difference between them. For GIV, for both regions, there were significant lower numbers of AC when compared to GIII. As observed, with HE, there were hyperplastic and dysplastic ACF in the proximal and distal portions of the colon. For IHQ analyses, there were positively PCNA antibody marked cells in all experimental groups. Yet, there was no significant correlation of mitotic index among them. Moreover, the results of GIII compared to GIV were very similar. Conclusion: In this sense, the Zingiber officinale essential oil has good antioxidant potential because it presents a mixture of monoterpene and sesquiterpene compounds. Thus, it is able to develop a chemoprotective effect, as it presented similar results to the standard drug, showing cell proliferation control.

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Section: Discussionsupporting

confidence: 89%

Evaluation of Antineoplasic Activity of Zingiber Officinale Essential Oil in the Colorectal Region of Wistar Rats

Lima

Pelegrini

Uechi

et al. 2020

Asian Pac J Cancer Prev

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“…More recently, Souza and co-authors evaluated the anti-Mycobacterium tuberculosis activity of 17 novel synthesized thiosemicarbazones derived from (−)-camphene, in vitro. Overall, the majority of the tested compounds exhibited significant inhibitory effects on the Mycobacterium tuberculosis growth, with minimal inhibitory concentrations (MIC) values ranged from 3.9 to > 250 µg/mL [209]. Although there are not as much reports about β-ocimene and camphene as was described to the other compounds here reviewed thus far, their repellent and/or insecticide activity seem to be promising.…”

Section: β-Ocimene and Camphenementioning

confidence: 90%

Terpenoids, Cannabimimetic Ligands, beyond the Cannabis Plant

et al. 2020

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Medicinal use of Cannabis sativa L. has an extensive history and it was essential in the discovery of phytocannabinoids, including the Cannabis major psychoactive compound—Δ9-tetrahydrocannabinol (Δ9-THC)—as well as the G-protein-coupled cannabinoid receptors (CBR), named cannabinoid receptor type-1 (CB1R) and cannabinoid receptor type-2 (CB2R), both part of the now known endocannabinoid system (ECS). Cannabinoids is a vast term that defines several compounds that have been characterized in three categories: (i) endogenous, (ii) synthetic, and (iii) phytocannabinoids, and are able to modulate the CBR and ECS. Particularly, phytocannabinoids are natural terpenoids or phenolic compounds derived from Cannabis sativa. However, these terpenoids and phenolic compounds can also be derived from other plants (non-cannabinoids) and still induce cannabinoid-like properties. Cannabimimetic ligands, beyond the Cannabis plant, can act as CBR agonists or antagonists, or ECS enzyme inhibitors, besides being able of playing a role in immune-mediated inflammatory and infectious diseases, neuroinflammatory, neurological, and neurodegenerative diseases, as well as in cancer, and autoimmunity by itself. In this review, we summarize and critically highlight past, present, and future progress on the understanding of the role of cannabinoid-like molecules, mainly terpenes, as prospective therapeutics for different pathological conditions.

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“…Drugs like triapine and thiacetazone are also examples of bioactive TSCs. 13,19 Their capacity to intercalate with DNA or stop DNA biosynthesis in cells is thought to be the cause of their bioactivity. 20,21 Furthermore, heterocyclic TSCs generally target intracellular moieties like N-myc downstream-regulated gene-1 (NDRG1) and DNA topoisomerase IIa and ribonucleotide reductase (top2a).…”

Section: Introductionmentioning

confidence: 99%

Exploring the anticancer potential of thiadiazole derivatives of substituted thiosemicarbazones formed via copper‐mediated cyclization

Palakkeezhillam

Haribabu

Kumar

et al. 2023

Applied Organom Chemis

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A couple of N‐(4)‐morpholine/pyrrolidine‐substituted thiosemicarbazones (TSCs) of fluorene‐2‐carboxaldehyde (FM and FP), and their corresponding thiadiazoles (TDZs) (CFM and CFP), were synthesized and characterized (elemental analysis, ultraviolet–visible [UV–Visible], Fourier transform infrared [FT‐IR], nuclear magnetic resonance [NMR; 1H & 13C], high‐resolution mass spectrometry [HRMS], and single‐crystal X‐ray diffraction [SCXRD]) for the evaluation of their anticancer potential. The TDZs were obtained unexpectedly and are possibly formed via single‐step metal (copper)‐mediated oxidative cyclizations of the TSCs. The synthesized compounds are fairly stable in phosphate buffer at the biological pH of 7.4. The density functional theory [DFT] studies were performed to predict the optimized structures and physicochemical properties of these compounds. The compounds were further subjected to computational and experimental biomolecular investigations in order to evaluate their anticancer activity in detail. CFM had the most potent activity against human breast adenocarcinoma (MCF‐7) and human urinary bladder (T24) cancer cells, with IC50 values of 12.00 and 24.80 μM, respectively. In contrast, CFM had negligible cytotoxicity (IC50 = 98.70 μM) against kidney epithelial cells extracted from an African green monkey (Vero) normal cells. This outcome was preferable to that of the widely used medicine Cisplatin. Molecular docking studies were performed with the breast cancer protein “cytochrome P450 1A1” (CYP1A1) and bovine serum albumin (BSA) to predict how effectively the compounds bind to the receptor. The ADMET findings suggest that these compounds have considerable drug‐likeness and oral bioavailability. These insights may open the door for additional medical research into the bioactivities of TSCs and TDZs produced from bioactive carbonyl compounds.

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Synthesis of novel (-)-Camphene-based thiosemicarbazones and evaluation of anti-Mycobacterium tuberculosis activity

Cited by 23 publications

References 21 publications

Evaluation of Antineoplasic Activity of Zingiber Officinale Essential Oil in the Colorectal Region of Wistar Rats

Evaluation of Antineoplasic Activity of Zingiber Officinale Essential Oil in the Colorectal Region of Wistar Rats

Terpenoids, Cannabimimetic Ligands, beyond the Cannabis Plant

Exploring the anticancer potential of thiadiazole derivatives of substituted thiosemicarbazones formed via copper‐mediated cyclization

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