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M7068

Sigma-Aldrich

MPP dihydrochloride hydrate

≥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

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

Storage Class Code

11 - Combustible Solids

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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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.
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
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
Ke-Wei Zhang et al.
Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology, 237, 110328-110328 (2019-08-29)
Insulin-like growth factors (Igf1 and Igf2) play a key role in growth and development of vertebrates. In mammals, the expression of IGFs is regulated by estradiol-17β (E2) via estrogen receptors (ESRs). The expression of igfs can also be regulated by
Junqiang Yan et al.
Aging, 12(9), 8107-8119 (2020-05-14)
Neuroinflammation and oxidative stress play key roles in the pathological development of Parkinson's disease (PD). Nerve growth factor-induced gene B (Nur77) is closely related to dopamine neurotransmission, and its pathogenesis is unclear. This study aims to investigate the role and
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