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Purity: =99.93%
Diphencyprone, formerly known as DPCP and Diphenylcyclopropenone, is a topically administered drug intended for treating alopecia areata and alopecia totalis. Topical immunotherapy using diphenylcyclopropenone may also be an effective treatment option for recalcitrant warts. Diphenylcyclopropenone acts as a local irritant, triggering a local sensitization. It triggers an immune response that opposes the action of the autoreactive cells that otherwise cause hair loss.
| Targets |
Immunomodulator
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|---|---|
| ln Vitro |
Topical immunotherapy with diphenylcyclopropenone (DPCP) is considered to be the most effective treatment of severe AA. However, the mechanism is unclear and an early predictor for the efficacy needs to be explored. The TSLP/OX40L/IL-13 pathway is an important pathway to initiate and maintain Th2 immune responses. Our previous work suggests this pathway may play a role in severe AA treated with DPCP. Thus, to further investigate the mechanism of TSLP/OX40L/IL-13 pathway in severe AA treated with DPCP and explore the predictor for the efficacy of DPCP therapy, we conducted a prospective study to compare expression levels of TSLP, OX40L, Th2 cytokines IL-4, IL-5 and IL13, and Th1 cytokine IFN-γ in severe AA patients before and after the treatment. Results showed that 21 AA patients were responsive (responders) to the DPCP therapy and 12 were not responsive (non-responders). Responders had lower levels of TSLP, OX40L and IL-13 than non-responders before the treatment. After the DPCP treatment, TSLP, IL-5 and IL-13 increased and IFN-γ decreased in responders while there were no changes of TSLP, IL-4, IL-13 and IFN-γ in non-responders. Our data suggest that the TSLP/OX40L/IL-13 pathway is down-regulated in some severe AA patients and DPCP might play a therapeutic role by up-regulating the pathway in these severe AA patients. The TSLP/OX40L/IL-13 pathway could be a predictor of response to the DPCP therapy for severe AA patients[1].
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| ln Vivo |
Diphenylcyclopropenone enhanced antigen-specific IgG2a antibody responses as well as IL-10 cytokine production after epicutaneous immunization with ovalbumin (OVA). Epicutaneous allergen-specific immunotherapy (EPIT) with OVA and DCP also protected sensitized mice from anaphylaxis and asthma. The protective effect was more robust than that of conventional SCIT, which did not significantly alleviate the symptoms of allergy in the murine models of anaphylaxis and asthma.
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| Cell Assay |
Changes of cell-surface thiols induced by chemical treatment may affect the conformations of membrane proteins and intracellular signaling mechanisms. In our previous study, we found that a non-toxic dose of diphenylcyclopropene (DPCP), which is a potent skin sensitizer, induced an increase of cell-surface thiols in cells of a human monocytic cell line, THP-1. Here, we examined the influence of DPCP on intracellular signaling. First, we confirmed that DPCP induced an increase of cell-surface thiols not only in THP-1 cells, but also in primary monocytes. The intracellular reduced-form glutathione/oxidized-form glutathione ratio (GSH/GSSG ratio) was not affected by DPCP treatment. By means of labeling with a membrane-impermeable thiol-reactive compound, Alexa Fluor 488 C5 maleimide (AFM), followed by two-dimensional gel electrophoresis and analysis by liquid chromatography coupled with electrospray tandem mass spectrometry (LC/MS/MS), we identified several proteins whose thiol contents were modified in response to DPCP. These proteins included cell membrane components, such as actin and β-tubulin, molecular chaperones, such as heat shock protein 27A and 70, and endoplasmic reticulum (ER) stress-inducible proteins. Next, we confirmed the expression in DPCP-treated cells of spliced XBP1, a known marker of ER stress. We also detected the phosphorylation of SAPK/JNK and p38 MAPK, which are downstream signaling molecules in the IRE1α-ASK1 pathway, which is activated by ER stress. These data suggested that increase of cell-surface thiols might be associated with activation of ER stress-mediated signaling[3].
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| Animal Protocol |
In a mouse model of allergy, we tested the adjuvant potential of diphenylcyclopropenone (DCP), a strong contact sensitizer, which is currently used for the treatment of a T cell-mediated hair loss disease (alopezia areata).[3]
Female CBA mice were used at the age of 6–8 weeks. Before epicutaneous immunization, mice were shaved on their belly (2 × 2 cm). After 4 h, the mice were anaesthetized with xylazin 8 mg/kg and ketamine 50 mg/kg intraperitoneally (i.p.) 13. The skin was tape stripped 10 times with a scotch tape. Thereafter, the mice were immunized with 25-μg ovalbumin (OVA; Grade V) dissolved in water/acetone/dibutylphthalate (1 : 1 : 2) ± 1% DCP. The vaccination was repeated after 7, 14, and 28 days (Fig. 1A). Sham controls were treated with the vehicle with 1% DCP. For reference, some mice were immunized four times subcutaneously with 25-μg OVA in PBS/aluminum hydroxide (2 : 1). |
| References |
[1]. Yugang Gong, et al. Diphenylcyclopropenone plays an effective therapeutic role by up-regulating the TSLP/OX40L/IL-13 pathway in severe alopecia areata. Exp Dermatol. 2021 Feb;30(2):278-283.
[2]. Zekayi Kutlubay, et al. Assessment of treatment efficacy of diphenylcyclopropenone (DPCP) for alopecia areata. Turk J Med Sci. 2020 Dec 17;50(8):1817-1824. [3]. Changes of cell-surface thiols and intracellular signaling in human monocytic cell line THP-1 treated with diphenylcyclopropenone. J Toxicol Sci. 2010 Dec;35(6):871-9. [4]. The contact sensitizer diphenylcyclopropenone has adjuvant properties in mice and potential application in epicutaneous immunotherapy. Allergy. 2012 May;67(5):638-46. |
| Additional Infomation |
Diphenylcyclopropenone is a cyclopropenone compound having phenyl substituents at the 2- and 3-positions. It has a role as a photosensitizing agent, a hapten and a drug allergen.
Diphencyprone has been used in trials studying the treatment and basic science of Melanoma, Ultraviolet Rays, Immunosuppression, Neoplasm Metastasis, and Hypersensitivity, Delayed, among others. Diphencyprone is a synthetic, potent allergic contact sensitizer with potential immunostimulatory activity. After sensitization process by repeated topical application of diphencyprone to a specific area, further application of this agent to the affected area may stimulate an immune response and may potentially be useful to clear the affected area from infection or cancer. |
| Molecular Formula |
C15H10O
|
|---|---|
| Molecular Weight |
206.244
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| Exact Mass |
206.073
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| Elemental Analysis |
C, 87.36; H, 4.89; O, 7.76
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| CAS # |
886-38-4
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| Related CAS # |
886-38-4;
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| PubChem CID |
65057
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| Appearance |
Typically exists as Off-white to light yellow solids at room temperature
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
407.2±45.0 °C at 760 mmHg
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| Melting Point |
118-122 °C(lit.)
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| Flash Point |
182.7±23.7 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.669
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| LogP |
3.78
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
16
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| Complexity |
284
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C1C(C2C=CC=CC=2)=C1C1C=CC=CC=1
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| InChi Key |
HCIBTBXNLVOFER-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H10O/c16-15-13(11-7-3-1-4-8-11)14(15)12-9-5-2-6-10-12/h1-10H SMILES
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| Chemical Name |
2,3-Diphenylcycloprop-2-en-1-one
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| Synonyms |
Diphencyprone; DPCP; Diphenylcyclopropenone; Diphencyprone; 2,3-Diphenylcycloprop-2-en-1-one; 2,3-Diphenylcycloprop-2-enone; 2,3-Diphenylcyclopropenone; 1,2-Diphenylcyclopropen-3-one; Cyclopropenone, diphenyl-;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~484.87 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.12 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (12.12 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (12.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8487 mL | 24.2436 mL | 48.4872 mL | |
| 5 mM | 0.9697 mL | 4.8487 mL | 9.6974 mL | |
| 10 mM | 0.4849 mL | 2.4244 mL | 4.8487 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05481658 | RECRUITING | Drug: Diphencyprone (DPCP) | Cutaneous Metastases | Nicholas Gulati | 2022-10-06 | Phase 1 |
| NCT04775979 | COMPLETED | Drug: diphenylcyclopropenone (DPCP) | Vitiligo | Ain Shams University | 2021-01-17 | Phase 4 |
| NCT01452594 | COMPLETED | Drug: Diphenylcyclopropenone Drug: Placebo |
Healthy Volunteers | Rockefeller University | 2011-10 | |
| NCT05438290 | COMPLETED | Drug: DPCP | Cutaneous Neurofibroma | Nicholas Gulati | 2022-09-14 | Phase 1 |
| NCT01711684 | COMPLETED | Drug: Diphenylcyclopropenone (DPCP) | Melanoma Neoplasm Metastasis |
Rockefeller University | 2012-10-16 | Phase 1 |
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