First synthesis of rugosaflavonoid and its derivatives and their activity against breast cancer

Puranik, Ninad V.; Srivastava, Pratibha

doi:10.1039/c7ra04971d

Cited by 11 publications

(21 citation statements)

References 23 publications

(22 reference statements)

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“…29,30 Before formation of rugosaflavonoids, we had obtained dihydrorugosaflavonoids (Scheme 1). 30,31 We had screened these compounds for tuberculosis in our previous studies, and we found that halogenated dihydrorugosaflavonoids were much better antitubercular agents than rugosaflavonoids. 31 Due to nonavailability of the antiviral drug against CHIKV, mostly natural compounds have been subjected to screening for antiviral activity to obtain lead molecules using highthroughput assays.…”

Section: ■ Introductionmentioning

confidence: 99%

Evaluation of the Antiviral Potential of Halogenated Dihydrorugosaflavonoids and Molecular Modeling with nsP3 Protein of Chikungunya Virus (CHIKV)

et al. 2019

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Antiviral therapy is crucial for the circumvention of viral epidemics. The unavailability of a specific antiviral drug against the chikungunya virus (CHIKV) disease has created an alarming situation to identify or develop potent chemical molecules for remedial management of CHIKV. In the present investigation, in silico studies of dihydrorugosaflavonoid derivatives (5a–f) with non-structural protein-3 (nsP3) were carried out. nsP3 replication protein has recently been considered as a possible antiviral target in which crucial inhibitors fit into the adenosine-binding pocket of the macrodomain. The 4′-halogenated dihydrorugosaflavonoids displayed intrinsic binding with the nsp3 macrodomain (PDB ID: 3GPO) of CHIKV. Compounds 5c and 5d showed docking scores of −7.54 and −6.86 kcal mol–1, respectively. Various in vitro assays were performed to confirm their (5a–f) antiviral potential against CHIKV. The non-cytotoxic dose was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay and was found to be <100 μM. The compounds 5c and 5d showed their inhibitory potential for CHIKV, which was determined through cytopathic effect assay and plaque reduction assay, which show inhibition up to 95 and 92% for 70 μM concentration of the compounds, respectively. The quantitative real-time polymerase chain reaction assay result confirmed the ability of 5c and 5d to reduce the viral RNA level at 70 μM concentration of compounds to nearly 95 and 93% concentration, respectively, in cells with CHIKV infection. Further, the CHIKV-inhibitory capacity of these compounds was corroborated by execution of immunofluorescence assay. The executed work will be meaningful for the future research of studied dihydrorugosaflavonoids against prime antiviral entrants, leading to remedial management to preclude CHIKV infection.

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Section: ■ Introductionmentioning

confidence: 99%

Evaluation of the Antiviral Potential of Halogenated Dihydrorugosaflavonoids and Molecular Modeling with nsP3 Protein of Chikungunya Virus (CHIKV)

et al. 2019

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“…In our ongoing research to develop simple and cost-effective synthetic methodologies for naturally occurring chromones, we have reported the first total synthesis of rugosaflavonoid and its derivatives and identified their cytotoxic potential towards breast cancer cells. 10 Recently, Villaume et al 11 performed structure–activity relationship (SAR) studies and identified mandatory sites that are necessary for a flavone molecule to exhibit anti-TB activity. As the molecules synthesized in the present study ( Scheme 1 ) possess the same backbone, this encouraged us to perform molecular docking studies of the active sites of β-ketoacyl-ACP reductase (MabA) (PDB ID: IUZN) and pantothenate kinase (PanK) (PDB ID: ).…”

Section: Introductionmentioning

confidence: 99%

Molecular modeling studies and in vitro screening of dihydrorugosaflavonoid and its derivatives against Mycobacterium tuberculosis

et al. 2018

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“…Notably, the residues Phe699, Lys721, Met769, Thr830 and Asp831 of wtEGFR involved in the binding with natural products, which is observed in methanone ( Singh and Bast, 2014 ). In addition, rugosaflavanoid derivatives were bound with the residues Leu694 and Gly772 exhibited anticancer activity, which is also observed with methanone ( Puranik et al, 2017 ). In addition, oxazole interacted with residues Met769, Lys721, Thr830, and Asp831 of wtEGFR, along with residues Phe771, Cys773, Leu694, Leu768, and Gly772 which were reported as key interactions ( Singh and Bast, 2014 ).…”

Section: Resultsmentioning

confidence: 78%

Identification of novel bioactive molecules from garlic bulbs: A special effort to determine the anticancer potential against lung cancer with targeted drugs

Padmini¹,

Maheshwari²,

Saravanan³

et al. 2020

Saudi Journal of Biological Sciences

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Garlic ( Allium sativum L.), is a predominant spice, which is used as an herbal medicine and flavoring agent, since ancient times. It has a rich source of various secondary metabolites such as flavonoids, terpenoids and alkaloids, which have various pharmacological properties. Garlic is used in the treatment of various ailments such as cancer, diabetes and cardiovascular diseases. The present study aims to explore the plausible mechanisms of the selected phytocompounds as potential inhibitors against the known drug targets of non-small-cell lung cancer (NSCLC). The phytocompounds of garlic were identified by gas chromatography-mass spectrometry (GC–MS) technique. Subsequently, the identified phytocompounds were subjected to molecular docking to predict the binding with the drug targets, epidermal growth factor receptor (EGFR), human epidermal growth factor receptor 2 (HER2), echinoderm microtubule-associated protein-like 4-anaplastic lymphoma kinase (EML4-ALK) and group IIa secretory phospholipase A2 (sPLA2-IIA). Molecular dynamics is used to predict the stability of the identified phytocompounds against NSCLC drug targets by refining the intermolecular interactions formed between them. Among the 12 phytocompounds of garlic, three compounds[1,4-dimethyl-7-(1-methylethyl)-2-azulenyl]phenylmethanone, 2,4-bis(1-phenylethyl)-phenol and 4,5–2 h-oxazole-5-one,4-[3,5-di-t-butyl-4-methoxyphenyl] methylene-2-phenyl were identified as potential inhibitors, which might be suitable for targeting the different clinical forms of EGFR and dual inhibition of the studied drug targets to combat NSCLC. The result of this study suggest that these identified phytocompounds from garlic would serve as promising leads for the development of lead molecules to design new multi-targeting drugs to address the different clinical forms of NSCLC.

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First synthesis of rugosaflavonoid and its derivatives and their activity against breast cancer

Abstract: Ligand interaction of 6f with 1M17.

Cited by 11 publications

References 23 publications

Evaluation of the Antiviral Potential of Halogenated Dihydrorugosaflavonoids and Molecular Modeling with nsP3 Protein of Chikungunya Virus (CHIKV)

Evaluation of the Antiviral Potential of Halogenated Dihydrorugosaflavonoids and Molecular Modeling with nsP3 Protein of Chikungunya Virus (CHIKV)

Molecular modeling studies and in vitro screening of dihydrorugosaflavonoid and its derivatives against Mycobacterium tuberculosis

Identification of novel bioactive molecules from garlic bulbs: A special effort to determine the anticancer potential against lung cancer with targeted drugs

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