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Cat. No.: HY-189016

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ORG 2058

ORG 2058 is a progesterone receptor agonist with a K_d of 1.25-1.68 nM. ORG 2058 exhibits nuclear uptake/retention, activates progesterone-specific receptor-chromatin binding, induces apoptosis, inhibits normal breast epithelial proliferation and bcl-2/bclxL expression, and induces hydroxysteroid dehydrogenase activity. ORG 2058 can be used in breast cancer research.

For research use only. We do not sell to patients.

CAS No.: 24320-06-7
Formula: C₂₂H₃₂O₃
Molecular Weight:344.49

Storage:

Please store the product under the recommended conditions in the Certificate of Analysis.

ORG 2058 Chemical Structure

CAS No.: 24320-06-7

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Use of MCE Products

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- IC₅₀ & Target
- In Vitro
- In Vivo
Chemical Information
Purity & Documentation
References
Calculators
Help & FAQs
Classifications
Bioz

Biological Activity

Description

IC₅₀ & Target

^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]^[9]

progesterone receptor

1.25-1.68 nM (Kd)

Bcl-2

Bcl-xL

All Bcl-2 Family Isoforms :

In Vitro

ApoptosisAnti-cancerOthers

Apoptosis

ORG 2058 (100 nM; 4 days) is proapoptotic in normal human breast epithelial cells, with the highest potency among the tested progestins^[3].
ORG 2058 (100 nM; 48 h) strongly inhibits bcl-2 and slightly reduces bcl-xL in normal human breast epithelial cells without altering Bax or bak^[3].

Apoptosis

Anti-cancer

ORG 2058 (100 nM; 3 days) is proapoptotic in T47-D breast cancer cells, and E2 attenuates this effect^[3].
ORG 2058 (100 nM; 8-48 h) inhibits bcl-2 expression in ZR75-1 cells by 8 hours and further at 48 hours and reduces bcl-xL to 70% of control^[3].

Others

ORG 2058 in human and calf cytosols binds PR with an equilibrium dissociation constant of 1.25-1.68 nM^[2].
ORG 2058 (100 nM; days 4-6) is antiproliferative in normal human breast epithelial cells in medium A^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Proliferation Assay^[3]

Cell Line:

Normal human breast epithelial cells
Concentration:

100 nM
Incubation Time:

2; 3; 4; 5; 6 days
Result:

Inhibited the proliferation of normal human mammary epithelial cells.

Apoptosis Analysis^[3]

Cell Line:

T47-D breast cancer cells
Concentration:

100 nM (alone); 10 nM E2 + 100 nM (combination)
Incubation Time:

3 days
Result:

Increased apoptosis to 160%.

Western Blot Analysis^[3]

Cell Line:

ZR75-1 breast cancer cells
Concentration:

100 nM
Incubation Time:

8 h; 48 h
Result:

Inhibited bcl-2 expression as soon as 8 hours after exposure, with a greater effect at 48 hours.
bcl-xL expression was decreased to 70% of control.

In Vivo

ORG 2058 (2.5 μg/kg; i.v.; single injection; 1 h) concentrates in nuclei of a minority of alveolar secretory cells and in interlobular duct and connective tissue cells in estrogen-primed baboons, while unlabeled progesterone co-injection diminishes this nuclear labeling^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Baboon^[1]
Dosage:

2.5 μg/kg body weight
Administration:

i.v.; single injection; 1 h
Result:

Nuclear uptake and retention were observed in secretory and stromal elements, with unlabeled cytoplasm.
Only 13.4% of alveolar secretory cells examined were labeled (n = 3816), while 60.2% of alveoli contained at least one labeled epithelial cell per cross-section (n = 260).
Individual secretory cells heavily concentrated radioactivity in their nuclei.
Most epithelial cells of interlobular ducts were labeled.
Fibroblasts of the interlobular connective tissue were heavily labeled, but fat cells were not labeled.
No cells of the intralobular connective tissue were labeled.
In the animal co-injected with unlabeled Progesterone, nuclear labeling in all aforementioned cell types was absent or significantly diminished.

Related Protocols :

Chemical Information

CAS No. 24320-06-7
Molecular Weight 344.49
Formula C₂₂H₃₂O₃
SMILES

C[C@@]12[C@](C[C@H]([C@@H]2C(CO)=O)CC)([H])[C@@]3([H])[C@]([C@]4([H])C(CC3)=CC(CC4)=O)([H])CC1
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Weaker FJ, et al. Autoradiographic localization of3H-ORG 2058, a synthetic progestin, in the mammary glands of the baboon. Breast Cancer Research and Treatment. 1984 Jun;4(2):143-7.

[2]. Traish AM, et al. 7α-17α-Dimethyl-19-nortestosterone (mibolerone) induces conformational changes in progesterone receptors distinct from those induced by ORG 2058. Steroids. 1994 Jun 1;59(6):362-70.

[3]. Gompel A, et al. In vitro studies of tibolone in breast cells. Fertility and sterility. 2002 Aug;78(2):351-9.

[4]. Geier A, et al. Differences in the association of the progesterone receptor ligated by antiprogestin RU38486 or progestin ORG 2058 to chromatin components. Biochimica et biophysica acta. 1987 Oct 22;931(1):78-86.

[5]. Bakos T, et al. Steroids 51. An improved synthesis of ORG 2058 and the synthesis of [3H]ORG 2058. Steroids. 1993 Mar;58(3):115-8.

[6]. Koga M, et al. Modulation of the growth-inhibitory effects of progestins and the antiestrogen hydroxyclomiphene on human breast cancer cells by epidermal growth factor and insulin. Cancer research. 1989 Jan 1;49(1):112-6.

[7]. Šauer P, et al. Two synthetic progestins and natural progesterone are responsible for most of the progestagenic activities in municipal wastewater treatment plant effluents in the Czech and Slovak republics. Water research. 2018 Jun 15;137:64-71.

[8]. Houtman CJ, et al. Characterisation of (anti-)progestogenic and (anti-)androgenic activities in surface and wastewater using high resolution effectdirected analysis. Environment international. 2021 Aug;153:106536.

[9]. Heubner A, et al. High-performance and ion-exchange chromatography and chromatofocusing of the human uterine progesterone receptor: its application to the identification of 21-[3H] dehydro org 2058-labelled receptor. Journal of Chromatography A. 1984 Aug 2;297:301-11.

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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Biological Activity
- Description
- IC₅₀ & Target
- In Vitro
- In Vivo
Chemical Information
Purity & Documentation
References

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ORG 2058

All Bcl-2 Family Isoforms