MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 206704 | Name: Diphencyprone
Featured New

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Diphencyprone (DPCP) is a small-molecule contact sensitizer primarily used in dermatology for conditions like alopecia areata and warts. DPCP induces antigen-presenting cell activation, particularly by upregulating major histocompatibility complex (MHC) molecules and increasing cytokine secretion, such as IL-1β, IL-6, and TNF-α, in dendritic cells and keratinocytes. It has been shown to activate nuclear factor kappa B (NF-κB) signaling, leading to an inflammatory response. Additionally, DPCP exposure results in the recruitment and proliferation of T cells, particularly CD8+ cytotoxic T lymphocytes, which contribute to its immunomodulatory effects.

Chemical Structure

Diphencyprone
Diphencyprone
CAS#886-38-4

Theoretical Analysis

MedKoo Cat#: 206704

Name: Diphencyprone

CAS#: 886-38-4

Chemical Formula: C15H10O

Exact Mass: 206.0732

Molecular Weight: 206.24

Elemental Analysis: C, 87.36; H, 4.89; O, 7.76

Price and Availability

Size Price Availability Quantity
200mg USD 90.00 Ready to ship
500mg USD 150.00 Ready to ship
1g USD 250.00 Ready to ship
2g USD 450.00 Ready to ship
5g USD 750.00 2 weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Diphencyprone; DPCP and Diphenylcyclopropenone,
IUPAC/Chemical Name
2,3-Diphenylcycloprop-2-en-1-one
InChi Key
HCIBTBXNLVOFER-UHFFFAOYSA-N
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 Code
O=C1C(C2=CC=CC=C2)=C1C3=CC=CC=C3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#A7L05F26
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Diphenylcyclopropenone (Diphencyprone) is a topical immunomodulatory agent.
In vitro activity:
The influence of DPCP on intracellular signaling was examined. DPCP induced an increase of cell-surface thiols not only in THP-1 cells, but also in primary monocytes. Sseveral proteins were identified 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. The expression in DPCP-treated cells of spliced XBP1, a known marker of ER stress, was confirmed. The phosphorylation of SAPK/JNK and p38 MAPK, which are downstream signaling molecules in the IRE1α-ASK1 pathway, which is activated by ER stress, was also detected. These data suggested that increase of cell-surface thiols might be associated with activation of ER stress-mediated signaling. Reference: J Toxicol Sci. 2010 Dec;35(6):871-9. https://www.jstage.jst.go.jp/article/jts/35/6/35_6_871/_article
In vivo activity:
The adjuvant potential of diphenylcyclopropenone (DCP), a strong contact sensitizer, was tested in a mouse model of allergy. 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 (subcutaneous allergen-specific immunotherapy) which did not significantly alleviate the symptoms of allergy in the murine models of anaphylaxis and asthma. Reference: Allergy. 2012 May;67(5):638-46. https://onlinelibrary.wiley.com/doi/abs/10.1111/j.1398-9995.2012.02802.x
Solvent mg/mL mM
Solubility
DMF 20.0 96.97
DMSO 20.0 96.97
DMSO:PBS (pH 7.2) (1:1) 0.5 2.42
Ethanol 14.0 67.88
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 206.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Hirota M, Motoyama A, Suzuki M, Yanagi M, Kitagaki M, Kouzuki H, Hagino S, Itagaki H, Sasa H, Kagatani S, Aiba S. 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. doi: 10.2131/jts.35.871. PMID: 21139337. 2. von Moos S, Johansen P, Waeckerle-Men Y, Mohanan D, Senti G, Häffner A, Kündig TM. The contact sensitizer diphenylcyclopropenone has adjuvant properties in mice and potential application in epicutaneous immunotherapy. Allergy. 2012 May;67(5):638-46. doi: 10.1111/j.1398-9995.2012.02802.x. Epub 2012 Mar 2. PMID: 22380933.
In vitro protocol:
1. Hirota M, Motoyama A, Suzuki M, Yanagi M, Kitagaki M, Kouzuki H, Hagino S, Itagaki H, Sasa H, Kagatani S, Aiba S. 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. doi: 10.2131/jts.35.871. PMID: 21139337.
In vivo protocol:
1. von Moos S, Johansen P, Waeckerle-Men Y, Mohanan D, Senti G, Häffner A, Kündig TM. The contact sensitizer diphenylcyclopropenone has adjuvant properties in mice and potential application in epicutaneous immunotherapy. Allergy. 2012 May;67(5):638-46. doi: 10.1111/j.1398-9995.2012.02802.x. Epub 2012 Mar 2. PMID: 22380933.
1: Mousavian P, Mashayekhi Goyonlo V, Javanbakht M, Reza Jafari M, Moosavian H, Afzal Aghaei M, Malekzadeh M. Diphencyprone reduces the CD8+ lymphocytes and IL-4 and enhences IgG2a/IgG1 ratio in pathogenicity of acute leishmania major infection in BALB/c mice. Cytokine. 2024 Dec;184:156792. doi: 10.1016/j.cyto.2024.156792. Epub 2024 Nov 2. PMID: 39488893. 2: Poplausky D, Young JN, Block BR, Estrada Y, Singer GK, Wong V, Cabral P, Suemitsu Y, Kim RH, Friedlander P, Gulati N. Case report: Regression of in- transit metastases of cutaneous squamous cell carcinoma with combination pembrolizumab and topical diphencyprone. Front Oncol. 2024 May 10;14:1294331. doi: 10.3389/fonc.2024.1294331. PMID: 38800408; PMCID: PMC11116557. 3: Pham JP, Dwyer L, Phan K, Menzies AM, Frew JW. Efficacy of topical diphencyprone for melanoma in-transit metastases: a systematic review and meta- analysis. Melanoma Res. 2023 Oct 1;33(5):434-436. doi: 10.1097/CMR.0000000000000914. Epub 2023 Aug 29. PMID: 37650727. 4: Mehta H, Jack C, Maari C, Proulx ÉS, Bissonnette R, Ramirez-Valle F, Sarfati M. Oral prednisone regulates human skin T cells in delayed-type hypersensitivity reaction elicited by diphencyprone. Allergy. 2023 Aug;78(8):2255-2265. doi: 10.1111/all.15764. Epub 2023 May 19. PMID: 37163280. 5: Chadha M, Walsh S, du Vivier A. A large case series on the use of diphencyprone immunotherapy in the clearance of palmoplantar warts. Clin Exp Dermatol. 2023 Feb 2;48(2):96-99. doi: 10.1093/ced/llac046. PMID: 36730505. 6: Han J, Agarwal A, Young JN, Owji S, Luu Y, Poplausky D, Yassky D, Estrada Y, Ungar J, Krueger JG, Gulati N. Proteomic profiling of a patient with cutaneous melanoma metastasis regression following topical contact sensitizer diphencyprone and immune checkpoint inhibitor treatment. Sci Rep. 2022 Dec 26;12(1):22364. doi: 10.1038/s41598-022-27020-1. PMID: 36572780; PMCID: PMC9792448. 7: Han J, Correa da Rosa J, Owji S, Yassky D, Luu Y, Estrada Y, Ungar J, Ji A, Krueger JG, Gulati N. Skin proteomic analysis of immune activation associated with regression of melanoma metastases induced by diphencyprone. JAAD Int. 2022 Aug 23;9:65-68. doi: 10.1016/j.jdin.2022.08.006. PMID: 36147215; PMCID: PMC9486131. 8: Díaz-Guimaraens B, Saceda-Corralo D, Hermosa-Gelbard Á, Moreno-Arrones ÓM, Dominguez-Santas M, Suarez-Valle A, Vañó-Galván S. Imiquimod-enhanced immunotherapy with diphencyprone for patients with alopecia areata. Dermatol Ther. 2022 Jul;35(7):e15516. doi: 10.1111/dth.15516. Epub 2022 Apr 20. PMID: 35421278. 9: Rocha VB, Kakizaki P, Donati A, Machado CJ, Pires MC, Contin LA. Randomized controlled study comparing the use of diphencyprone and anthralin in the treatment of extensive chronic alopecia areata. An Bras Dermatol. 2021 May- Jun;96(3):372-376. doi: 10.1016/j.abd.2020.06.018. Epub 2021 Mar 16. PMID: 33849753; PMCID: PMC8178552. 10: Abedini R, Alipour E, Ghandi N, Nasimi M. Utility of Dermoscopic Evaluation in Predicting Clinical Response to Diphencyprone in a Cohort of Patients with Alopecia Areata. Int J Trichology. 2020 May-Jun;12(3):107-113. doi: 10.4103/ijt.ijt_73_20. Epub 2020 Aug 14. PMID: 33223734; PMCID: PMC7659740. 11: Foo HL, Lee JSS, Wang ECE. Discoid lupus erythematosus precipitated by topical diphencyprone immunotherapy for alopecia areata. JAAD Case Rep. 2020 Jun 4;6(8):747-750. doi: 10.1016/j.jdcr.2020.05.037. PMID: 32715069; PMCID: PMC7369523. 12: Lôbo MM, Calsavara VF, Ricci BV, Lopes Pinto CA, Bertolli E, Duprat Neto JP. Response rates of cutaneous melanoma metastases to diphencyprone: A meta- analysis. J Am Acad Dermatol. 2020 Dec;83(6):1812-1813. doi: 10.1016/j.jaad.2020.04.023. Epub 2020 Apr 11. PMID: 32289400. 13: Manimaran RP, Ramassamy S, Rajappa M, Chandrashekar L. Therapeutic outcome of diphencyprone and its correlation with serum cytokine profile in alopecia areata. J Dermatolog Treat. 2022 Feb;33(1):324-328. doi: 10.1080/09546634.2020.1752887. Epub 2020 May 21. PMID: 32249656. 14: Lo MC, Garioch J, Moncrieff MD. Sequencing in management of in-transit melanoma metastasis: Diphencyprone versus isolate limb infusion. J Plast Reconstr Aesthet Surg. 2020 Jul;73(7):1263-1267. doi: 10.1016/j.bjps.2020.03.007. Epub 2020 Mar 17. PMID: 32245735. 15: Kaptanoglu AF, Özgen Z, Demir G, Cömert E. An Easy, Cheap, and User-Friendly Technique for Topical Immunotherapy With Diphencyprone: Cotton Tip Injector Technique. Indian Dermatol Online J. 2020 Jan 13;11(1):119. doi: 10.4103/idoj.IDOJ_97_19. PMID: 32055528; PMCID: PMC7001399. 16: Happle R. Diphencyprone: the career of a strong contact sensitizer in clinical dermatology. J Eur Acad Dermatol Venereol. 2019 Nov;33(11):2012-2013. doi: 10.1111/jdv.15942. PMID: 31713911. 17: Leeyaphan C, Tantrapornpong P, Ungprasert P. The efficacy of diphencyprone immunotherapy for the treatment of cutaneous warts: a systematic review and meta-analysis. J Dermatolog Treat. 2021 Sep;32(6):658-662. doi: 10.1080/09546634.2019.1688230. Epub 2019 Nov 20. PMID: 31679413. 18: Parkinson E, Aleksic M, Arthur R, Regufe Da Mota S, Cubberley R, Skipp PJ. Proteomic analysis of haptenation by skin sensitisers: Diphencyprone and ethyl acrylate. Toxicol In Vitro. 2020 Feb;62:104697. doi: 10.1016/j.tiv.2019.104697. Epub 2019 Oct 24. PMID: 31669365. 19: Nahidi Y, Mashayekhi Goyonlo V, Layegh P, Taghavi F, Najaf Najafi M. Immunomodulatory effects of topical diphencyprone for the treatment of acute urban cutaneous leishmaniasis. J Dermatolog Treat. 2021 Mar;32(2):220-226. doi: 10.1080/09546634.2019.1642997. Epub 2019 Aug 1. PMID: 31294619. 20: Bullen A, Polcz M, Rowe CJ, Byrom L, Soyer HP, Khosrotehrani K. Level of contact hypersensitivity response to diphencyprone and keratinocyte cancer. J Eur Acad Dermatol Venereol. 2019 Nov;33(11):2101-2105. doi: 10.1111/jdv.15766. Epub 2019 Jul 19. PMID: 31265155.