Synthesis of 1,2,3-Triazole Derivatives of Hydnocarpic Acid Isolated from Carpotroche brasiliensis Seed Oil and Evaluation of Antiproliferative Activity

Osorio, Liseth S.; Ionta, Marisa; Demuner, Antônio J.; Sousa, Bianca Lana de; Ferraz, Guilherme O.; Varejão, Eduardo Vinícius Vieira; Ferreira-Silva, Guilherme Álvaro; Pilau, Eduardo Jorge; Silva, Evandro; Santos, Marcelo H. dos

doi:10.21577/0103-5053.20200125

Cited by 6 publications

(6 citation statements)

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“…[34] The 1,2,3-triazole conjugate of hydnocarpic acid, (R)-[1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl]methyl-11-(cyclopent-2-en-1-yl)undecanoate (13) showed promising antiproliferative activity F I G U R E 1 Biologically active 1,2,3-triazole drugs F I G U R E 2 Mechanisms of action of 1,2,3-triazole hybrids with an IC 50 value of 63.96 μM, which was 2.5-fold more effective than hydnocarpic acid (157 μM) against A549 cells. [35] As a novel 1,2,3-triazole derivative of ametantrone, 14 showed cytotoxic effects with IC 50 values of 13.5, 4.5, 13.1, and 9.8 μM on A431, BxPC3, HCT-15, and CCD-34Lu, respectively [36] (Figure 3).…”

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confidence: 99%

1,2,3‐Triazole hybrids as anticancer agents: A review

Alam

2021

Archiv der Pharmazie

148

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Despite the advancements in the development of anticancer agents, more effective and safer anticancer drugs still need to be developed as the current agents cause unwanted side effects and many patients have become drug resistant. 1,2,3-Triazoles, due to their remarkable biological potential, have received considerable attention in drug discovery for the development of anticancer agents. The present review article presents an overview of the recent advances in 1,2,3-triazole hybrids with anticancer potential over the last 2 years, their chemical structures, structure-activity relationships, and mechanisms of action, as well as insights into the docking studies.

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confidence: 99%

1,2,3‐Triazole hybrids as anticancer agents: A review

Alam

2021

Archiv der Pharmazie

148

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“…The NMR of the isolated constituent was taken by dissolving it in dimethyl sulfoxide (DMSO). 1 H-NMR and 13 C-NMR showed different peaks for different types of protons and 13 C present in the structure of HA [12]. DSC DSC thermogram was obtained in the temperature range of 40°-400°C at 15°C/min rate on the Pyris 6 DSC instrument and the scan was obtained [13].…”

Section: Nmrmentioning

confidence: 99%

Development of solid lipid nanoparticle gel for transdermal delivery system of chaulmoogra oil

Parveen

Samal

Nafis³

et al. 2023

Exploration of Medicine

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Aim: The main objective of the study was to formulate, evaluate and perform an optimization study of chaulmoogra oil-loaded solid lipid nanoparticles (SLNs) based gel. Methods: The study involves isolation, identification, and quantification of hydnocarpic acid (HA), using high-performance thin-layer chromatography (HPTLC) and characterization using ultraviolet (UV), nuclear magnetic resonance (NMR), and mass spectroscopy (MS), and differential scanning calorimetry (DSC). Different concentration of assorted solid lipids and surfactants was used for the preparation of SLN gel with the improved transdermal application. Size distribution, entrapping efficiency, transmission electron microscopy (TEM), and percent yield were tested for the prepared SLN and the characterization of SLN gel was evaluated on the basis of in vitro diffusion study, stability studies, homogeneity, and skin irritancy test. Results: The amount of HA quantified in the oil sample was found to be 54.84% w/w. The percent yield and entrapment efficiency (EE) of HA SLNs were 96.176 ± 1.338% and 90.2 ± 0.5% respectively. The in vitro percent cumulative drug release was 80.89% for the developed SLN, the homogeneity test showed no grittiness, and the prepared gel was found to be effective as it shows no signs of erythema post-treatment of 10 days. The in vitro dissolution studies showed better results for SLN gel when compared to SLN suspension. Conclusions: The nano-gel could be a better option for the topical delivery of herbal drugs with improved bioavailability providing several benefits over conventional formulation.

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“…First semisynthetic therapeutic products derived from chaulmoogric acid were already patented in 1941 (Orlando et al 1941); recently (Osorio et al 2020), a series of novel triazole derivatives based on hydnocarpic acid conjugation have been synthesized showing promising antineoplastic activity against human cell lines from lung carcinoma. Furthermore, the chaulmoogra oil, rich in hydnocarpic acid, is an ingredient in a patented cosmetic formulation for the treatment of depigmented or non-pigmented skin (Leconte and Leclere 2012).…”

Section: Hydnocarpic Acid and Chaulmoogric Acidmentioning

confidence: 99%

Rare fatty acids and lipids in plant oilseeds: occurrence and bioactivity

Avato

Tava²

2021

Phytochem Rev

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Lipids are biomolecules which are present in plants as general metabolites with different functions such as structural, protective and also as storage material. Plants produce a high number of different fatty acids: the most common structural types are long linear hydrocarbon chains, saturated or unsaturated with an even number of carbon atoms. In addition, plants accumulate rare fatty acids with reference to their occurrence and to their structures such as number and arrangement of unsaturated bonds, chain branches, type of functional groups, cyclic structures and halogenation. Their presence is limited in plant leaves, roots or stems, while they are mostly found as components of storage seed oils. The present review aims to describe the structural features of selected unusual rare fatty acids occurring in plants, their bioactivity and applications as pharmaceutical, cosmetic, food and non-food industrial products. Cyanolipids, a group of rare natural lipids containing a cyanogenic group in the molecule and only found in seed oils of a few plant species are also commented.

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Synthesis of 1,2,3-Triazole Derivatives of Hydnocarpic Acid Isolated from Carpotroche brasiliensis Seed Oil and Evaluation of Antiproliferative Activity

Cited by 6 publications

References 0 publications

1,2,3‐Triazole hybrids as anticancer agents: A review

1,2,3‐Triazole hybrids as anticancer agents: A review

Development of solid lipid nanoparticle gel for transdermal delivery system of chaulmoogra oil

Rare fatty acids and lipids in plant oilseeds: occurrence and bioactivity

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