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M7068

MPP dihydrochloride hydrate

Name: MPP dihydrochloride hydrate
Brand: SIGMA

≥97% (HPLC), powder, estrogen receptor α agonist

Synonym(s):

1,3-Bis(4-hydroxyphenyl)-4-methyl-5-[4-(2-piperidinylethoxy)phenol]-1H-pyrazole dihydrochloride hydrate, Methyl-piperidino-pyrazole hydrate

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₃₁N₃O₃· 2 HCl · xH₂O

CAS Number:

911295-24-4

Molecular Weight:

542.50 (anhydrous basis)

MDL number:

MFCD06411603

UNSPSC Code:

51111800

PubChem Substance ID:

24724540

NACRES:

NA.77

product name

MPP dihydrochloride hydrate, ≥97% (HPLC), white, powder

Quality Level

100

Assay

≥97% (HPLC)

form

powder

storage condition

desiccated

color

white

solubility

DMSO: soluble ≥20 mg/mL

SMILES string

Cl.Cl.Cc1c(nn(-c2ccc(O)cc2)c1-c3ccc(OCCN4CCCCC4)cc3)-c5ccc(O)cc5

InChI

1S/C29H31N3O3.2ClH/c1-21-28(22-5-11-25(33)12-6-22)30-32(24-9-13-26(34)14-10-24)29(21)23-7-15-27(16-8-23)35-20-19-31-17-3-2-4-18-31;;/h5-16,33-34H,2-4,17-20H2,1H3;2*1H

InChI key

FWDNPWVVRVSJQH-UHFFFAOYSA-N

General description

Methyl-piperidino-pyrazole hydrate (MPP) is prepared from a methyl-pyrazole-triol (MPT), a pyrazole triol.

Application

MPP dihydrochloride hydrate has been used as an estrogen receptor α antagonist:

in human breast cancer MCF-7 cells
to pre-treat endometrial ex vivo organ cultures (EVOCs)
to treat pituitary glands to monitor luteinizing hormone secretion

Biochem/physiol Actions

MPP dihydrochloride is a specific estrogen receptor α antagonist.

Methyl-piperidino-pyrazole hydrate (MPP) is an agonist for estrogen receptor α and lacks any ligand functionality with estrogen receptor (ER)β. It promotes silibinin induced apoptosis in human breast cancer MCF-7 cells.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Icariin Alleviates Wear Particle-Induced Periprosthetic Osteolysis via Down-Regulation of the Estrogen Receptor α-mediated NF-κB Signaling Pathway in Macrophages.

Fu Guangtao et al.

Frontiers in pharmacology, 12, 746391-746391 (2021-11-23)

Periprosthetic osteolysis is one of the major long-term complications following total joint replacement. Its cause is widely accepted to be wear particle-induced activation of inflammatory macrophages. No effective strategy for the prevention and treatment of periprosthetic osteolysis is yet available.

Localization of estrogen receptor ERα, ERβ and GPR30 on myenteric neurons of the gastrointestinal tract and their role in motility.

Julia Y H Liu et al.

General and comparative endocrinology, 272, 63-75 (2018-12-06)

Estrogen is well known to have a modulatory role on gastrointestinal tract, particularly through its interaction with nuclear estrogen receptors (ERs), alpha and beta (ERα/β). Recent functional studies also indicate that estrogen can activate a G-protein coupled estrogen receptor, GPR30

Analogs of methyl-piperidinopyrazole (MPP): antiestrogens with estrogen receptor alpha selective activity.

Hai-Bing Zhou et al.

Bioorganic & medicinal chemistry letters, 19(1), 108-110 (2008-11-19)

Methyl-piperidino-pyrazole (MPP), an estrogen receptor alpha (ERalpha)-selective antagonist we developed, has a basic side chain (BSC) attached to an ERalpha-selective agonist ligand, methyl-pyrazole-triol (MPT) through an ether linkage. To remove the possibility that metabolic cleavage of the BSC in MPP

ERα down-regulation plays a key role in silibinin-induced autophagy and apoptosis in human breast cancer MCF-7 cells.

Nan Zheng et al.

Journal of pharmacological sciences, 128(3), 97-107 (2015-06-29)

The estrogen receptor alpha (ERα) has been proven to be one of the most important therapeutic targets in breast cancer over the last 30 years. Previous studies pointed out that a natural flavonoid, silibinin, induced apoptosis in human breast cancer

Estrogen prevent atherosclerosis by attenuating endothelial cell pyroptosis via activation of estrogen receptor α-mediated autophagy.

Qinghai Meng et al.

Journal of advanced research, 28, 149-164 (2020-12-29)

Excessive inflammation and the pyroptosis of vascular endothelial cells caused by estrogen deficiency is one cause of atherosclerosis in post-menopausal women. Because autophagy is highly regulated by estrogen, we hypothesized that estrogen can reduce vascular endothelial cell pyroptosis through estrogen

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