PHTPP | CAS#805239-56-9 | ERß receptor antagonist

MedKoo Cat#: 562451 | Name: PHTPP

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Description:

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

PHTPP is an estrogen ERß receptor antagonist.

Chemical Structure

PHTPP

CAS#805239-56-9

Theoretical Analysis

MedKoo Cat#: 562451

Name: PHTPP

CAS#: 805239-56-9

Chemical Formula: C20H11F6N3O

Exact Mass: 423.0806

Molecular Weight: 423.32

Elemental Analysis: C, 56.75; H, 2.62; F, 26.93; N, 9.93; O, 3.78

Price and Availability

Size	Price	Availability
50mg	USD 550.00	2 Weeks
100mg	USD 950.00	2 Weeks
200mg	USD 1,450.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,450.00	2 Weeks
2g	USD 5,450.00	2 Weeks

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Related CAS #

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Synonym

PHTPP;

IUPAC/Chemical Name

4-[2-Phenyl-5,7-bis(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-3-yl]phenol

InChi Key

AEZPAUSGTAHLOQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H11F6N3O/c21-19(22,23)14-10-15(20(24,25)26)29-18(27-14)16(11-6-8-13(30)9-7-11)17(28-29)12-4-2-1-3-5-12/h1-10,30H

SMILES Code

OC1=CC=C(C2=C3N=C(C(F)(F)F)C=C(C(F)(F)F)N3N=C2C4=CC=CC=C4)C=C1

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

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

Instruction

View handling instruction

Biological target:

PHTPP is a selective estrogen receptor β (ERβ) antagonist.

In vitro activity:

The most distinctive ligand in this series, 2-phenyl-3-(4-hydroxyphenyl)-5,7-bis(trifluoromethyl)-pyrazolo[1,5-a]pyrimidine, was 36-fold selective for ERbeta in binding. Curiously, on the basis of molecular modeling, the ERbeta binding selectivity of compounds in this series appears to be derived from differing orientations that they adapt in the ligand binding pockets of ERalpha vs ERbeta. In transcription assays this pyrazolopyrimidine was fully effective as an ERbeta antagonist while exhibiting no significant activity on ERalpha. Reference: J Med Chem. 2004 Nov 18;47(24):5872-93. https://pubmed.ncbi.nlm.nih.gov/15537344/

In vivo activity:

Using in vitro cell lines and an in vivo carcinogen N-butyl-N-(4-hydroxybutyl) nitrosamine (BBN)-induced mouse BCa model, this study found that ERβ plays a positive role in promoting BCa progression. Supportively, treating cells with the ERβ-specific antagonist, 4-[2-Phenyl-5,7-bis(trifluoromethyl) pyrazolo[1,5-a]pyrimidin-3-yl]phenol (PHTPP), reduced BCa cell growth and invasion, as well as MCM5 expression. Furthermore, this study provides the first evidence that BCa burden and mortality can be controlled by PHTPP treatment in the carcinogen-induced BCa model. Reference: Carcinogenesis. 2014 Mar;35(3):651-61. https://pubmed.ncbi.nlm.nih.gov/24148819/

	Solvent	mg/mL	mM
Solubility
	DMF	50.0	118.11
	DMSO	34.7	82.07
	DMSO:PBS (pH 7.2) (1:3)	0.3	0.59
	Ethanol	52.1	123.10

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 423.32 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.

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. Ogo Y, Taniuchi S, Ojima F, Hayashi S, Murakami I, Saito Y, Takeuchi S, Kudo T, Takahashi S. IGF-1 gene expression is differentially regulated by estrogen receptors α and β in mouse endometrial stromal cells and ovarian granulosa cells. J Reprod Dev. 2014;60(3):216-23. doi: 10.1262/jrd.2013-085. Epub 2014 Mar 25. PMID: 24670778; PMCID: PMC4085386. 2. Compton DR, Sheng S, Carlson KE, Rebacz NA, Lee IY, Katzenellenbogen BS, Katzenellenbogen JA. Pyrazolo[1,5-a]pyrimidines: estrogen receptor ligands possessing estrogen receptor beta antagonist activity. J Med Chem. 2004 Nov 18;47(24):5872-93. doi: 10.1021/jm049631k. Erratum in: J Med Chem. 2005 Apr 7;48(7):2724. PMID: 15537344. 3. Luo F, Guo H, Yu H, Li Y, Feng Y, Wang Y. PM2.5 organic extract mediates inflammation through the ERβ pathway to contribute to lung carcinogenesis in vitro and vivo. Chemosphere. 2021 Jan;263:127867. doi: 10.1016/j.chemosphere.2020.127867. Epub 2020 Aug 6. PMID: 32841872. 4. Hsu I, Chuang KL, Slavin S, Da J, Lim WX, Pang ST, O'Brien JH, Yeh S. Suppression of ERβ signaling via ERβ knockout or antagonist protects against bladder cancer development. Carcinogenesis. 2014 Mar;35(3):651-61. doi: 10.1093/carcin/bgt348. Epub 2013 Oct 22. PMID: 24148819.

In vitro protocol:

In vivo protocol:

1. Luo F, Guo H, Yu H, Li Y, Feng Y, Wang Y. PM2.5 organic extract mediates inflammation through the ERβ pathway to contribute to lung carcinogenesis in vitro and vivo. Chemosphere. 2021 Jan;263:127867. doi: 10.1016/j.chemosphere.2020.127867. Epub 2020 Aug 6. PMID: 32841872. 2. Hsu I, Chuang KL, Slavin S, Da J, Lim WX, Pang ST, O'Brien JH, Yeh S. Suppression of ERβ signaling via ERβ knockout or antagonist protects against bladder cancer development. Carcinogenesis. 2014 Mar;35(3):651-61. doi: 10.1093/carcin/bgt348. Epub 2013 Oct 22. PMID: 24148819.

1: Yu J, Zhang Y, Yao H, Zhang Z, Yang X, Zhu W, Xu J. ERβ activation improves nonylphenol-induced depression and neurotransmitter secretion disruption via the TPH2/5-HT pathway. Ecotoxicol Environ Saf. 2024 Jul 15;280:116521. doi: 10.1016/j.ecoenv.2024.116521. Epub 2024 Jun 8. PMID: 38850708. 2: Hu Z, Chen L, Zhao J, Zhang W, Jin Z, Sun Y, Li Z, Chang B, Shen P, Yang Y. Lipoxin A4 ameliorates knee osteoarthritis progression in rats by antagonizing ferroptosis through activation of the ESR2/LPAR3/Nrf2 axis in synovial fibroblast-like synoviocytes. Redox Biol. 2024 Jul;73:103143. doi: 10.1016/j.redox.2024.103143. Epub 2024 Mar 30. PMID: 38754271; PMCID: PMC11126537. 3: Li F, Zhu J, Liu J, Hu Y, Wu P, Zeng C, Lu R, Wu N, Xue Q. Targeting Estrogen Receptor Beta Ameliorates Diminished Ovarian Reserve via Suppression of the FOXO3a/Autophagy Pathway. Aging Dis. 2024 Feb 25. doi: 10.14336/AD.2024.0221. Epub ahead of print. PMID: 38421826. 4: Hassan HA, Mohamed Abdelhamid A, Samy W, Osama Mohammed H, Mortada Mahmoud S, Fawzy Abdel Mageed A, Abbas NAT. Ameliorative effects of androstenediol against acetic acid-induced colitis in male wistar rats via inhibiting TLR4-mediated PI3K/Akt and NF-κB pathways through estrogen receptor β activation. Int Immunopharmacol. 2024 Jan 25;127:111414. doi: 10.1016/j.intimp.2023.111414. Epub 2023 Dec 22. PMID: 38141404. 5: Liu M, Guo P, Zeng M, Zhang Y, Jia J, Liu Y, Chen X, Kuang H, Feng W, Zheng X. Effects and mechanisms of frehmaglutin D and rehmaionoside C improve LPS- induced acute kidney injury through the estrogen receptor-mediated TLR4 pathway in vivo and in vitro. Phytomedicine. 2024 Jan;123:155218. doi: 10.1016/j.phymed.2023.155218. Epub 2023 Nov 14. PMID: 37980806. 6: Leite BA, Bezerra PHA, Stocco B, Abichabki N, Andrade LN, Fonseca MJV, Torqueti MR. Biotransformed soybean cream as a new nutraceutical for skin care: collagen stimulation in vitro and ex vivo. Braz J Med Biol Res. 2023 Oct 20;56:e12781. doi: 10.1590/1414-431X2023e12781. PMID: 37878883; PMCID: PMC10591485. 7: Lin P, Zhang X, Zhu B, Gao J, Yin D, Zeng J, Kang Z. Naringenin protects pancreatic β cells in diabetic rat through activation of estrogen receptor β. Eur J Pharmacol. 2023 Dec 5;960:176115. doi: 10.1016/j.ejphar.2023.176115. Epub 2023 Oct 21. PMID: 37866740. 8: Li J, Yao X, Wu Y, Wang C, Yang J, Wu C. The anticonvulsant effect of saiga horn on febrile seizures by regulating brain serotonin content and inhibiting neuroinflammation. J Ethnopharmacol. 2024 Jan 30;319(Pt 1):117180. doi: 10.1016/j.jep.2023.117180. Epub 2023 Sep 12. PMID: 37709104. 9: Refaat B, Aslam A, Idris S, Almalki AH, Alkhaldi MY, Asiri HA, Almaimani RA, Mujalli A, Minshawi F, Alamri SA, AlHussain MI, Baltow BA, Alqasmi MH, Basfar GT, Alosaimi OM, Muhayya IA. Profiling estrogen, progesterone, and androgen receptors in colorectal cancer in relation to gender, menopausal status, clinical stage, and tumour sidedness. Front Endocrinol (Lausanne). 2023 May 3;14:1187259. doi: 10.3389/fendo.2023.1187259. PMID: 37206439; PMCID: PMC10190606. 10: Bano A, Stevens JH, Modi PS, Gustafsson JÅ, Strom AM. Estrogen Receptor β4 Regulates Chemotherapy Resistance and Induces Cancer Stem Cells in Triple Negative Breast Cancer. Int J Mol Sci. 2023 Mar 20;24(6):5867. doi: 10.3390/ijms24065867. PMID: 36982940; PMCID: PMC10058198. 11: Smiley CE, Pate BS, Bouknight SJ, Francis MJ, Nowicki AV, Harrington EN, Wood SK. Estrogen receptor beta in the central amygdala regulates the deleterious behavioral and neuronal consequences of repeated social stress in female rats. Neurobiol Stress. 2023 Feb 21;23:100531. doi: 10.1016/j.ynstr.2023.100531. PMID: 36879670; PMCID: PMC9984877. 12: Wesselman HM, Gatz AE, Pfaff MR, Arceri L, Wingert RA. Estrogen Signaling Influences Nephron Segmentation of the Zebrafish Embryonic Kidney. Cells. 2023 Feb 20;12(4):666. doi: 10.3390/cells12040666. PMID: 36831333; PMCID: PMC9955091. 13: Le G, Baumann CW, Warren GL, Lowe DA. In vivo potentiation of muscle torque is enhanced in female mice through estradiol-estrogen receptor signaling. J Appl Physiol (1985). 2023 Mar 1;134(3):722-730. doi: 10.1152/japplphysiol.00731.2022. Epub 2023 Feb 3. PMID: 36735234; PMCID: PMC10027088. 14: Wang M, Yang X, Zhou Q, Guo Y, Chen Y, Song L, Yang J, Li L, Luo L. Neuroprotective Mechanism of Icariin on Hypoxic Ischemic Brain Damage in Neonatal Mice. Oxid Med Cell Longev. 2022 Nov 15;2022:1330928. doi: 10.1155/2022/1330928. PMID: 36425058; PMCID: PMC9681555. 15: Queathem ED, Fitzgerald M, Welly R, Rowles CC, Schaller K, Bukhary S, Baines CP, Rector RS, Padilla J, Manrique-Acevedo C, Lubahn DB, Vieira-Potter VJ. Suppression of estrogen receptor beta classical genomic activity enhances systemic and adipose-specific response to chronic beta-3 adrenergic receptor (β3AR) stimulation. Front Physiol. 2022 Sep 16;13:920675. doi: 10.3389/fphys.2022.920675. PMID: 36213237; PMCID: PMC9534559. 16: Qiao D, Qin X, Yang H, Liu X, Liu L, Liu S, Jia Z. Estradiol mediates the interaction of LINC01541 and miR-429 to promote angiogenesis of G1/G2 endometrioid adenocarcinoma in-vitro: A pilot study. Front Oncol. 2022 Aug 5;12:951573. doi: 10.3389/fonc.2022.951573. PMID: 35992774; PMCID: PMC9389109. 17: Wu H, Zeng L, Ou J, Wang T, Chen Y, Nandakumar KS. Estrogen Acts Through Estrogen Receptor-β to Promote Mannan-Induced Psoriasis-Like Skin Inflammation. Front Immunol. 2022 May 19;13:818173. doi: 10.3389/fimmu.2022.818173. PMID: 35663991; PMCID: PMC9160234. 18: Li Q, Yang Y, Wang H, Jiang Z, Ma H. Genistein accelerates glucose catabolism via activation the GPER-mediated cAMP/PKA-AMPK signaling pathway in broiler chickens. Life Sci. 2022 Aug 15;303:120676. doi: 10.1016/j.lfs.2022.120676. Epub 2022 May 28. PMID: 35640778. 19: Azizian H, Farhadi Z, Khaksari M. Selective estrogen receptor α and β antagonist aggravate cardiovascular dysfunction in type 2 diabetic ovariectomized female rats. Horm Mol Biol Clin Investig. 2022 May 6;43(4):427-436. doi: 10.1515/hmbci-2021-0073. PMID: 35512107. 20: Wang J, Zhang L, Cao H, Shi X, Zhang X, Gao Z, Ikeda K, Yan T, Jia Y, Xu F. Silibinin improves L-cell mass and function through an estrogen receptor- mediated antioxidative mechanism. Phytomedicine. 2022 May;99:154022. doi: 10.1016/j.phymed.2022.154022. Epub 2022 Feb 27. PMID: 35255283.