Haplopine
Based on 1 Customer Validation
Haplopine is a substance with anti-inflammatory, antioxidant and photoactivated antibacterial activities. It also acts as an inhibitor of UGT1A7 and a photoactivated restriction endonuclease inhibitor. Haplopine inhibits the mRNA/protein expression of IL-6, TSLP, GM-CSF, G-CSF, IL-4, IL-13 and COX-2, while upregulating the mRNA/protein expression of SOD, CAT and HO-1. Haplopine inhibits the glucuronidation reaction catalyzed by UGT1A7 through competitive hydrophobic binding. Haplopine exerts photoactivated restriction endonuclease inhibitory effects by binding to DNA. Haplopine exhibits photoactivated activity against methicillin-resistant Staphylococcus aureus. Haplopine alleviates symptoms of atopic dermatitis. Haplopine can be used in research related to atopic dermatitis and methicillin-resistant Staphylococcus aureus infections.
For research use only. We do not sell to patients.
- Purity: 99.49%
- CAS No.: 5876-17-5
- Formula: C13H11NO4
- Molecular Weight:245.23
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Storage:
4°C, sealed storage, away from moisture and light
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| A549 | IC50 |
>10 μM
Compound: 9
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Cytotoxicity against human A549 cells by SRB assay
Cytotoxicity against human A549 cells by SRB assay
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[PMID: 18950230] |
| Neutrophil | IC50 |
57.32 μM
Compound: 9
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Antiinflammatory activity in human neutrophils assessed as fMLP-induced superoxide release after 5 mins by spectrometry
Antiinflammatory activity in human neutrophils assessed as fMLP-induced superoxide release after 5 mins by spectrometry
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[PMID: 17822293] |
Haplopine (12.5-25 μM; 0.5 h pre-incubation, 24 h stimulation) concentration-dependently inhibits the mRNA and protein expression of pro-inflammatory mediators IL-6, TSLP, GM-CSF and G-CSF in HaCaT cells stimulated with TNF-α/IFN-γ[1].
Haplopine (12.5-50 μM; 0.5 h pre-incubation, 24 h stimulation) inhibits the mRNA and protein expression of pro-inflammatory mediators IL-4, IL-13, and COX-2 in TNF-α/IFN-γ-stimulated Jurkat T cells[1].
Haplopine (12.5-50 μM; 0.5 h pre-incubation, 24 h stimulation) concentration-dependently restores the mRNA and protein expressions of antioxidant defense enzymes SOD, CAT and HO-1 in H2O2-stimulated Jurkat T cells[1].
Haplopine (0.5-100 μM; 30-120 min) competitively inhibits the 4-MU glucuronidation reaction catalyzed by recombinant human UGT1A7, with an IC50 of 13.4 μM, a Ki of 7.2 μM, and a calculated in vivo inhibition threshold of 0.72 μM[3].
Haplopine (100 μM; 30-120 min) inhibits the 4-MU glucuronidation reaction catalyzed by recombinant human UGT1A9 by 45% at a concentration of 100 μM[3].
Haplopine (100 μM; 30-120 min) inhibits the 4-MU glucuronidation reaction catalyzed by recombinant human UGT1A3 by 17% at a concentration of 100 μM[3].
Haplopine (100 μM; 30-120 min) inhibits 35% of the 4-MU glucuronidation reaction catalyzed by recombinant human UGT2B4 at a concentration of 100 μM[3].
Haplopine (12.5 nM/spot; overnight at 37°C) exhibits photoactivated antibacterial activity against methicillin-resistant Staphylococcus aureus after UVA irradiation, with a minimum inhibitory dose of 12.5 nM/spot, whereas it shows no activity in the dark[4].
Haplopine (100 nM/spot; overnight at 37°C) exhibits weak photoactivated antibacterial activity against Candida albicans, with a minimum inhibitory dose of 100 nM/spot under UVA irradiation, while it shows no activity in dark conditions[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:HaCaT human keratinocyte cell line
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Concentration:12.5 μM, 25 μM
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Incubation Time:0.5 h pre-incubation; 24 h stimulation
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Result:Inhibited TNF-α/IFN-γ-induced IL-6 mRNA expression by 42% at 25 μM.
Suppressed TNF-α/IFN-γ-induced increases in TSLP, GM-CSF, and G-CSF mRNA to 2.7, 1.9, and 1.9-fold versus vehicle controls, respectively, at 12.5 μM.
Reduced TNF-α/IFN-γ-induced increases in TSLP, GM-CSF, and G-CSF mRNA to 1.8, 1.2, and 1.2-fold versus vehicle controls, respectively, at 25 μM.
Reduced the protein levels of IL-6 and GM-CSF in a concentration-dependent manner, with 25 μM causing a greater reduction than 12.5 μM.
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Cell Line:Jurkat T human lymphocyte cell line
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Concentration:12.5 μM (protein analysis only), 25 μM, 50 μM
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Incubation Time:0.5 h pre-incubation; 24 h stimulation
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Result:Inhibited TNF-α/IFN-γ-induced IL-13 mRNA expression by 63% and COX-2 mRNA expression by 70% versus stimulated controls at 25 μM.
Inhibited TNF-α/IFN-γ-induced IL-13 mRNA expression by 89% and COX-2 mRNA expression by 100% versus stimulated controls at 50 μM.
Suppressed TNF-α/IFN-γ-induced IL-4 mRNA upregulation in a concentration-dependent manner.
Reduced COX-2 protein expression in a concentration-dependent manner.\nIncreased H2O2-reduced SOD mRNA activity to 0.86-fold at 25 μM and 0.91-fold at 50 μM versus vehicle controls.
Increased CAT mRNA activity to 0.84-fold versus vehicle controls at 50 μM.
Increased H2O2-reduced HO-1 mRNA levels to 0.79-fold at 25 μM and 0.88-fold at 50 μM versus vehicle controls.
Restored the reduced protein expressions of SOD, CAT, and HO-1 in a concentration-dependent manner.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Balb/c (6-week-old male, DNCB-induced atopic dermatitis)[1]
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Dosage:0.05%; 0.1%
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Administration:topical; daily; 14 days
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Result:Reduced clinical dermatitis scores by 50%, total serum IgE levels by 23%, mast cell infiltration by 61%, and epidermal thickening by 50% compared to DNCB-treated controls.
Reduced clinical dermatitis scores by 40%, total serum IgE levels by 41%, mast cell infiltration by 52%, and epidermal thickening by 60% compared to DNCB-treated controls.
Caused dose-dependent decreases in spleen weight relative to DNCB-treated controls.
Chemical Information
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CAS No. 5876-17-5
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Appearance Solid
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Molecular Weight 245.23
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Formula C13H11NO4
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Color White to off-white
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SMILES
OC1=CC=C2C(OC)=C3C(OC=C3)=NC2=C1OC
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Structure Classification
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Initial Source
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
4°C, sealed storage, away from moisture and light
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
Purity & Documentation
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Data Sheet (301 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
References
[1]. Kim TY, et al. Haplopine Ameliorates 2,4-Dinitrochlorobenzene-Induced Atopic Dermatitis-Like Skin Lesions in Mice and TNF-α/IFN-γ-Induced Inflammation in Human Keratinocyte. Antioxidants (Basel). 2021;10(5):806. Published 2021 May 19. [Content Brief]
[2]. Jeong GS, et al. Neuroprotective effects of constituents of the root bark of Dictamnus dasycarpus in mouse hippocampal cells. Arch Pharm Res. 2010;33(8):1269-1275. [Content Brief]
[3]. Li Y, et al. Inhibition of UDP-glucuronosyltransferases by different furoquinoline alkaloids. Xenobiotica. 2020;50(10):1170-1179. [Content Brief]
[4]. Hanawa F, et al. Photo-activated DNA binding and antimicrobial activities of furoquinoline and pyranoquinolone alkaloids from rutaceae. Planta Med. 2004 Jun;70(6):531-5. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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