Synthesis of 14-deoxy-11,12-didehydroandrographolide analogues as potential cytotoxic agents for cholangiocarcinoma

Sombut, Sudarat; Bunthawong, Rada; Sirion, Uthaiwan; Kasemsuk, Teerapich; Piyachaturawat, Pawinee; Suksen, Kanoknetr; Suksamrarn, Apichart; Saeeng, Rungnapha

doi:10.1016/j.bmcl.2017.10.063

Cited by 15 publications

(9 citation statements)

References 34 publications

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“…Nees. The previously reported studies of various potential herbs (extracts or isolated compounds/synthelic analogs) for CCA focused on their antiproliferative activities against CCA cell lines or antitumor activities in animal models, activities on cell invasion and migration, and underlying mechanisms or targets of their actions 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , …”

Section: Resultsmentioning

confidence: 99%

“…f.: IC 50 < 1 µM] 13 , 14 , 15 , followed by rhinacanthin C [from Rhinacanthus nasutus (L.) Kurz (Acanthaceae): IC 50 = 1.5 µM] 16 , compounds from D. membranacea Pierre ex Prain & Burkill: IC 50 = 1 – 2 µM 8 , andrographolide and analogs [from A. paniculata (Burm.f.) Nees: IC 50 = 3 µM] 17 , 18 , 19 , cantharidin and norcantharidin [from Mylabris phalerata (Pallas): IC 50 = 2 – 3 µM] 20 , isolated/synthetic compounds from Atalantia monophylla DC. (Rutaceae): IC 50 = 3 – 5 µM 21 , 22 , tiliacorinine [from Tiliacora triandra (Colebr.)…”

Section: Resultsmentioning

confidence: 99%

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The Role of Herbal Medicine in Cholangiocarcinoma Control: A Systematic Review

2022

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The growing incidence of cholangiocarcinoma (bile duct cancer) and limited treatment options stimulate a pressing demand for research and the development of new chemotherapeutics against cholangiocarcinoma. This study aimed to systematically review herbs and herb-derived compounds or herbal formulations that have been investigated for their anti-cholangiocarcinoma potential. Systematic literature searches were conducted in three electronic databases: PubMed, ScienceDirect, and Scopus. One hundred and twenty-three research articles fulfilled the eligibility critera and were included in the analysis (68 herbs, isolated compounds and/or synthetic analogs, 9 herbal formulations, and 119 compounds that are commonly found in several plant species). The most investigated herbs were Atractylodes lancea (Thunb.) DC. (Compositae) and Curcuma longa L. (Zingiberaceae). Only A. lancea (Thunb.) DC. (Compositae) has undergone the full process of nonclinical and clinical development to deliver the final product for clinical use. The extracts of A. lancea (Thunb.) DC. (Compositae), Garcinia hanburyi Hook.f. (Clusiaceae), and Piper nigrum L. (Piperaceae) exhibit antiproliferative activities against human cholangiocarcinoma cells (IC50 < 15 µg/mL). Cucurbitacin B and triptolide are herbal isolated compounds that exhibit the most promising activities (IC50 < 1 µM). A series of experimental studies (in vitro, in vivo, and humans) confirmed the anti-cholangiocarcinoma potential and safety profile of A. lancea (Thunb.) DC. (Compositae) and its active compounds atractylodin and β-eudesmol, including the capsule pharmaceutical of the standardized A. lancea (Thunb.) DC. (Compositae) extract. Future research should be focused on the full development of the candidate herbs to deliver products that are safe and effective for cholangiocarcinoma control.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

The Role of Herbal Medicine in Cholangiocarcinoma Control: A Systematic Review

2022

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“…Compound 2 was prepared from naturally occurring andrographolide 1 following the procedure reported by Sombut and co-workers …”

Section: Methodsmentioning

confidence: 99%

“…Compound 2 was prepared from naturally occurring andrographolide 1 following the procedure reported by Sombut and co-workers. 23 3.6. Synthesis of deoxy-Andrographolide Terminal Alkyne 3.…”

Section: Drugs and Chemicalsmentioning

confidence: 99%

Synthesis of deoxy-Andrographolide Triazolyl Glycoconjugates for the Treatment of Alzheimer’s Disease

Jatav

Pandey²,

Dwivedi³

et al. 2022

ACS Chem. Neurosci.

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A new andrographolide-based terminal alkyne 3 was synthesized in good yield from deoxy-andrographolide 2, obtained from a natural compound andrographolide 1, which in turn was isolated from the leaves of the plant Andrographis paniculata.Copper(I)-catalyzed azide−alkyne cycloaddition reaction of alkyne 3 with azido-sugars 4a−f furnished a library of andrographolidefastened triazolyl glycoconjugates 5a−f in good yields. The structures of these semisynthetic andrographolide derivatives were established by Fourier transform infrared, NMR, and mass spectroscopy. The compounds 5a−f were further evaluated against Alzheimer's disease (AD) using a scopolamine (SCOP)-induced memory impairment mice model. It was observed that antioxidant and anticholinesterase properties of these compounds contribute significantly toward their remarkable potential to improve cognitive functioning.

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“…Currently, there are few reports on drug treatments for CCA. Studies suggest that 14-deoxy-11, 12-didehydroandrographolide and curcumin may be the potential drugs for the treatment of CCA ( 10 , 11 ). Even with the large number of tested drugs, the results remain unsatisfactory.…”

Section: Introductionmentioning

confidence: 99%

Survival analysis of genome-wide profiles coupled with Connectivity Map database mining to identify potential therapeutic targets for cholangiocarcinoma

et al. 2018

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Cholangiocarcinoma (CCA) is one of the most common epithelial cell malignancies worldwide. However, its prognosis is poor. The aim of the present study was to examine the prognostic landscape and potential therapeutic targets for CCA. RNA sequencing data and clinical information were downloaded from The Cancer Genome Atlas (TCGA) dataset and processed. A total of 172 genes that were significantly associated with overall survival of patients with CCA were identified using the univariate Cox regression method. Bioinformatics tools were applied using the Kyoto Encyclopedia of Genes and Genomes (KEGG) and gene ontology (GO). It was identified that ‘Wnt signaling pathway’, ‘cytoplasm’ and ‘AT DNA binding’ were the three most significant GO categories of CCA survival-associated genes. ‘Transcriptional misregulation in cancer’ was the most significant pathway identified in the KEGG analysis. Using the Drug-Gene Interaction database, a drug-gene interaction network was constructed, and 31 identified genes were involved in it. The most meaningful potential therapeutic targets were selected via protein-protein and gene-drug interactions. Among these genes, polo-like kinase 1 (PLK1) was identified to be a potential target due to its significant upregulation in CCA. To rapidly find molecules that may affect these genes, the Connectivity Map was queried. A series of molecules were selected for their potential anti-CCA functions. 0297417-0002B and tribenoside exhibited the highest connection scores with PLK1 via molecular docking. These findings may offer novel insights into treatment and perspectives on the future innovative treatment of CCA.

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Synthesis of 14-deoxy-11,12-didehydroandrographolide analogues as potential cytotoxic agents for cholangiocarcinoma

Cited by 15 publications

References 34 publications

The Role of Herbal Medicine in Cholangiocarcinoma Control: A Systematic Review

The Role of Herbal Medicine in Cholangiocarcinoma Control: A Systematic Review

Synthesis of deoxy-Andrographolide Triazolyl Glycoconjugates for the Treatment of Alzheimer’s Disease

Survival analysis of genome-wide profiles coupled with Connectivity Map database mining to identify potential therapeutic targets for cholangiocarcinoma

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