Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation

Venkatasamy, Radhakrishnan; Faas, Laura; Young, Antony R.; Raman, Amala; Hider, Robert C.

doi:10.1016/j.bmc.2004.01.036

Cited by 70 publications

(57 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The spectral and analytical data of the synthesized piperine analogs were consistent with the previously reported data in the literature (Koul et al 2000;Sangwan et al 2008;Venkatasamy et al 2004). Piperic acid (PA1) was obtained by alkaline hydrolysis of piperine (PIP).…”

Section: Synthesis and Characterization Of Amide-substituted Piperinesupporting

confidence: 74%

Structure–activity relationship of piperine and its synthetic amide analogs for therapeutic potential to prevent experimentally induced ER stress in vitro

Hammad

Ravindran

Khalil

et al. 2017

Cell Stress and Chaperones

View full text Add to dashboard Cite

Endoplasmic reticulum (ER) is the key organelle involved in protein folding and maturation. Emerging studies implicate the role of ER stress in the development of chronic kidney disease. Thus, there is an urgent need for compounds that could ameliorate ER stress and prevent CKD. Piperine and its analogs have been reported to exhibit multiple pharmacological activities; however, their efficacy against ER stress in kidney cells has not been studied yet. Hence, the goal of this study was to synthesize amide-substituted piperine analogs and screen them for pharmacological activity to relieve ER stress using an in vitro model of tunicamycininduced ER stress using normal rat kidney (NRK-52E) cells. Five amide-substituted piperine analogs were synthesized and their chemical structures were elucidated by pertinent spectroscopic techniques. An in vitro model of ER stress was developed using tunicamycin, and the compounds of interest were screened for their effect on cell viability, and the expression of ER chaperone GRP78, the pro-apoptotic ER stress marker CHOP, and apoptotic caspases 3 and 12 (via western blotting). Our findings indicate that exposure to tunicamycin (0.5 μg/ mL) for 2 h induces the expression of GRP78 and CHOP, and apoptotic markers (caspase-3 and caspase-12) and causes a significant reduction in renal cell viability. Pre-treatment of cells with piperine and its cyclohexylamino analog decreased the tunicamycin-induced upregulation of GRP78 and CHOP and cell death. Taken together, our findings demonstrate that piperine and its analogs differentially regulate ER stress, and thus represent potential therapeutic agents to treat ER stressrelated renal disorders.

show abstract

Section: Synthesis and Characterization Of Amide-substituted Piperinesupporting

confidence: 74%

Structure–activity relationship of piperine and its synthetic amide analogs for therapeutic potential to prevent experimentally induced ER stress in vitro

Hammad

Ravindran

Khalil

et al. 2017

Cell Stress and Chaperones

View full text Add to dashboard Cite

show abstract

“…Synthesis of cinnamic acids. The syntheses of compounds 1ii [27], 2ii [28] and 3ii [29] have been previously reported. Compound 1i has been isolated in the cis-form by Chapman et al [30] whereas no evidence for the stereochemistry of 3i has been given [31,32].…”

Section: Chemistrymentioning

confidence: 99%

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

et al. 2014

View full text Add to dashboard Cite

Cinnamic acids have been identified as interesting compounds with antioxidant, anti-inflammatory and cytotoxic properties. In the present study, simple cinnamic acids were synthesized by Knoevenagel condensation reactions and evaluated for the above biological activities. Compound 4ii proved to be the most potent LOX inhibitor. Phenylsubstituted acids showed better inhibitory activity against soybean LOX, and it must be noted that compounds 4i and 3i with higher lipophilicity values resulted less active than compounds 2i and 1i. The compounds have shown very good activity in different antioxidant assays. The antitumor properties of these derivatives have been assessed by their 1/IC 50 inhibitory values in the proliferation of HT-29, A-549, OAW-42, MDA-MB-231, HeLa and MRC-5 normal cell lines. The compounds presented low antitumor activity considering the IC 50 values attained for the cell lines, with the exception of compound 4ii. Molecular docking studies were carried out on cinnamic acid derivative 4ii and were found to be in accordance with our experimental biological results.

show abstract

“…The melanin content was determined as previously described [36,37] with minor modifications. Cells were washed with PBS, harvested by trypsinization, and centrifuged for 10 minutes at 1500 g. The cell pellets were then dissolved in 1.4 M NaOH containing 14% DMSO during 2 hours incubation at 80 ºC.…”

Section: Melanin Assaymentioning

confidence: 99%

Effects of Quercetin on Mushroom Tyrosinase and B16-F10 Melanoma Cells

2007

View full text Add to dashboard Cite

Abstract:In searching for tyrosinase inhibitors from plants using L-3,4-dihydroxyphenylalanine (L-DOPA) as a substrate, quercetin was found to be partially oxidized to the corresponding o-quinone under catalysis by mushroom tyrosinase (EC 1.14.18.1). Simultaneously, L-DOPA was also oxidized to dopaquinone and both o-quinones were further oxidized, respectively. The remaining quercetin partially formed adducts with dopaquinone through a Michael type addition. In general, flavonols form adducts with dopaquinone as long as their 3-hydroxyl group is free. Quercetin enhanced melanin production per cell in cultured murine B16-F10 melanoma cells, but this effect may be due in part to melanocytotoxicity. The concentration leading to 50% viable cells lost was established as 20 µM and almost complete lethality was observed at 80 µM.

show abstract

Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation

Cited by 70 publications

References 10 publications

Structure–activity relationship of piperine and its synthetic amide analogs for therapeutic potential to prevent experimentally induced ER stress in vitro

Structure–activity relationship of piperine and its synthetic amide analogs for therapeutic potential to prevent experimentally induced ER stress in vitro

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

Effects of Quercetin on Mushroom Tyrosinase and B16-F10 Melanoma Cells

Contact Info

Product

Resources

About