Pheophytin a
Based on 1 Customer Validation
Pheophytin a is a multi-target inhibitor, anticancer agent, antioxidant and antiviral agent. Pheophytin a directly binds to and inhibits HCV-NS3/4A protease (IC50=0.89 μM) to block viral replication. Pheophytin a also scavenges free radicals, reduces ferric ions, and exhibits cytotoxic activity against breast cancer cells. Pheophytin a effectively inhibits LPS-induced production of nitric oxide, prostaglandin E2, NOS2 and COX-2, as well as various pro-inflammatory cytokines, by downregulating the transcription levels of inflammatory mediators and blocking the ERK1/2 and STAT-1 pathways. In a low nerve growth factor environment, Pheophytin a also enhances ERK1/2 phosphorylation and synergistically promotes neurite outgrowth through MAPK pathway. Pheophytin a can be used to investigate the pathogenic mechanisms of diseases including chronic hepatitis C, sepsis, breast cancer and Alzheimer's disease.
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- Pureza: 80.0%
- No. CAS: 603-17-8
- Fòrmula: C55H74N4O5
- Peso molecular:871.20
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Almacenamiento:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Actividad biológica
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Chemical Information
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- Referencias
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Help & FAQs
Actividad biológica
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ERK1 |
ERK2 |
COX-2 |
STAT1 |
At concentrations of 5-25 μM with a 30-min pre-incubation followed by 24 h of LPS stimulation, Pheophytin a exhibits cytotoxicity toward LPS-stimulated RAW 264.7 murine macrophages at 25 μM, but shows no such effect at 5 μM or 10 μM[1].
Pheophytin a (1-10 μM; pre-incubated for 30 min followed by LPS stimulation for 6 h) reduces LPS-induced NOS2 protein expression in RAW 264.7 mouse macrophages in a dose-dependent manner; when cells are pre-incubated with concentrations of 1, 5, or 10 μM for 30 min, the inhibitory effect at 10 μM is significant, whereas administration after LPS stimulation shows no effect[1].
Pheophytin a (1-10 μM; pre-incubated for 30 min, followed by LPS stimulation for 3 h) dose-dependently inhibits LPS-induced NOS2 mRNA expression in RAW 264.7 mouse macrophages when pre-incubated at concentrations of 1, 5 or 10 μM for 30 min, and exhibits significant inhibitory effects at all tested concentrations[1].
Pheophytin a (10 μM; pre-incubated for 30 min, 10-30 min after LPS stimulation) enhances LPS-induced ERK1/2 phosphorylation in RAW 264.7 mouse macrophages when cells are pre-incubated with 10 μM Pheophytin a for 30 min and proteins are harvested at 10, 15 or 30 min after LPS stimulation; its inhibitory effect on LPS-induced NO production is partially reversed by the ERK1/2 inhibitor U0126 (HY-12031A); Pheophytin a has no effect on LPS-induced phosphorylation of JNK, p38 or Akt[1].
The IC50 values of Pheophytin a microparticles for scavenging superoxide anion radicals and nitric oxide radicals are 200.5 μg/mL and 132.7 μg/mL, respectively; the IC50 value for cytotoxicity against MCF-7 human breast cancer cells is 35.9 μg/mL[2].
Pheophytin a (0.9-31.2 μg/mL; 48 h) dose-dependently potentiates nerve growth factor-induced neurite outgrowth in PC12 cells; the effect at 3.9 μg/mL is comparable to that of high-concentration nerve growth factor, which enhances the phosphorylation level of ERK1/2 without affecting the total ERK level or the phosphorylation levels of p38 and JNK[3].
Pheophytin a (100 nM-10 μM; 60 min) inhibits FmLP-induced chemotaxis of human polymorphonuclear leukocytes in a dose-dependent manner[4].
Pheophytin a (0.1-6 μM; 48-96 h) inhibits the expression of HCV proteins and RNA in HCV subgenomic replicon cells, with an IC50 of 4.97 μM, and exhibits synergistic anti-HCV activity with IFNa-2a[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:LPS-stimulated RAW 264.7 murine macrophages
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Concentration:10 μM
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Incubation Time:30 min pre-incubation; 10, 15, 30 min after LPS stimulation (protein harvest)
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Result:Significantly increased LPS-induced ERK1/2 phosphorylation. Showed no effect on LPS-induced JNK, p38, or Akt phosphorylation. Had its suppressive effect on LPS-induced NO production partially reversed by the ERK1/2 inhibitor U0126.
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Cell Line:PC12 rat phaeochromocytoma cells
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Concentration:3.9 μg/ml (in presence of 10 ng/ml NGF)
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Incubation Time:5 min (in presence of 10 ng/ml NGF)
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Result:Did not increase total ERK protein levels. Significantly enhanced the phosphorylation of ERK1/2 in PC12 cells treated with 10 ng/ml NGF, with activation levels similar to those induced by 50 ng/ml NGF alone. Did not stimulate phosphorylation of p38 or c-Jun N-terminal kinase (JNK) in PC12 cells.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:BALB/c (8 weeks old)[4]
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Dosage:80 nmol/20 μl; 800 nmol/20 μl
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Administration:topical; single application
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Result:Reduced TPA-induced ear edema to a mean ear disk weight of 12.2 ± 1.4 mg (P < 0.05 vs TPA alone).\nReduced TPA-induced ear edema to a mean ear disk weight of 8.6 ± 1.1 mg (P < 0.005 vs TPA alone).
Chemical Information
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No. CAS 603-17-8
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Appearance Solid
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Peso molecular 871.20
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Fòrmula C55H74N4O5
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Color Brown to black
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SMILES
COC([C@@H]1/C2=C([C@H]([C@@H]3C)CCC(OC/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=O)/N=C3/C=C(C(C)=C/4C=C)\NC4=C/C5=N/C(C(CC)=C5C)=C\C6=C(C)C(C1=O)=C2N6)=O
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Structure Classification
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Initial Source
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
Pureza y Documentación
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Ficha de datos (279 KB)
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SDS (251 KB)
- English - EN (251 KB)
- Français - FR (251 KB)
- Deutsch - DE (251 KB)
- Norwegian - NO (251 KB)
- Español - ES (251 KB)
- Swedish - SV (251 KB)
- Italian - IT (251 KB)
- Korean - KR (251 KB)
- Portuguese - PT (251 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Lin CY, et al. Pheophytin a inhibits inflammation via suppression of LPS-induced nitric oxide synthase-2, prostaglandin E2, and interleukin-1β of macrophages. Int J Mol Sci. 2014;15(12):22819-22834. Published 2014 Dec 9. [Content Brief]
[2]. Mohammed HA, et al. Formulation of Ethyl Cellulose Microparticles Incorporated Pheophytin A Isolated from Suaeda vermiculata for Antioxidant and Cytotoxic Activities. Molecules. 2019 Apr 17;24(8):1501. [Content Brief]
[3]. Ina A, et al. Pheophytin a, a low molecular weight compound found in the marine brown alga Sargassum fulvellum, promotes the differentiation of PC12 cells. Int J Dev Neurosci. 2007;25(1):63-68. [Content Brief]
[4]. Okai Y, et al. Potent anti-inflammatory activity of pheophytin a derived from edible green alga, Enteromorpha prolifera (Sujiao-nori). Int J Immunopharmacol. 1997;19(6):355-358. [Content Brief]
[5]. Wang SY, et al. Bioactivity-guided screening identifies pheophytin a as a potent anti-hepatitis C virus compound from Lonicera hypoglauca Miq. Biochem Biophys Res Commun. 2009;385(2):230-235. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Pheophytin a Related Classifications
HY-N12586 Related Classifications
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