O4I2
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MedKoo CAT#: 522505

CAS#: 165682-93-9

Description: O4I2 is a potent inducers of Oct3/4. O4I2 showed high activity in enforcing Oct3/4 expression. O4I2 is a new class of small molecules suitable for iPSC generation. The octamer-binding transcription factor 4 (Oct3/4) is a master gene in the transcriptional regulatory network of pluripotent cells. Repression of Oct3/4 in embryonic stem cells (ESCs) is associated with cell differentiation and loss of pluripotency, whereas forced overexpression in cooperation with other transcriptional factors, such as Nanog, Sox2, and Lin28, can reprogram somatic cells back into pluripotent cells, termed induced pluripotent stem cells (iPSCs).


Chemical Structure

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O4I2
CAS# 165682-93-9

Theoretical Analysis

MedKoo Cat#: 522505
Name: O4I2
CAS#: 165682-93-9
Chemical Formula: C12H11ClN2O2S
Exact Mass: 282.02298
Molecular Weight: 282.74
Elemental Analysis: C, 50.98; H, 3.92; Cl, 12.54; N, 9.91; O, 11.32; S, 11.34

Price and Availability

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25.0mg USD 150.0 Same Day
50.0mg USD 250.0 Same Day
100.0mg USD 450.0 Same Day
200.0mg USD 650.0 Same Day
500.0mg USD 1450.0 Same Day
1.0g USD 2450.0 Same Day
2.0g USD 3850.0 Same Day
5.0g USD 5850.0 2 Weeks
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Synonym: O4I2; O-4I2; O4I-2.

IUPAC/Chemical Name: ethyl 2-((4-chlorophenyl)amino)thiazole-4-carboxylate

InChi Key: ULUBAPWNHROTEU-UHFFFAOYSA-N

InChi Code: InChI=1S/C12H11ClN2O2S/c1-2-17-11(16)10-7-18-12(15-10)14-9-5-3-8(13)4-6-9/h3-7H,2H2,1H3,(H,14,15)

SMILES Code: O=C(C1=CSC(NC2=CC=C(Cl)C=C2)=N1)OCC

Appearance: White to off-white 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

Biological target: O4I2 is a potent Oct3/4 inducer that induces the expression of pluripotent-associated genes Lin28, Sox2 and Nanog, and suppresses Rex1.
In vitro activity: Repression of Oct3/4 in embryonic stem cells (ESCs) is associated with cell differentiation and loss of pluripotency, whereas forced overexpression in cooperation with other transcriptional factors, such as Nanog, Sox2, and Lin28, can reprogram somatic cells back into pluripotent cells, termed induced pluripotent stem cells (iPSCs). However, random integration and potential tumorigenic transformation caused by viral transduction limit the clinical application of iPSCs. By performing a cell-based high throughput screening (HTS) campaign, several potential small molecules were identified as inducers of Oct3/4 expression. A lead structure ethyl 2-((4-chlorophenyl)amino)-thiazole-4-carboxylate, termed O4I2 was reported, showing high activity in enforcing Oct3/4 expression. On the basis of chemical expansion, further derivatives having increased activities toward Oct3/4 induction have been identified. Thus, O4I2 and its derivatives should provide a new class of small molecules suitable for iPSC generation. J Med Chem. 2015 Aug 13;58(15):5742-50. https://pubmed.ncbi.nlm.nih.gov/26143659/
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 70.7

Preparing Stock Solutions

The following data is based on the product molecular weight 282.74 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. Gama-Brambila RA, Chen J, Zhou J, Tascher G, Münch C, Cheng X. A PROTAC targets splicing factor 3B1. Cell Chem Biol. 2021 May 11:S2451-9456(21)00211-7. doi: 10.1016/j.chembiol.2021.04.018. Epub ahead of print. PMID: 34048672. 2. Cheng X, Yoshida H, Raoofi D, Saleh S, Alborzinia H, Wenke F, Göhring A, Reuter S, Mah N, Fuchs H, Andrade-Navarro MA, Adjaye J, Gul S, Utikal J, Mrowka R, Wölfl S. Ethyl 2-((4-Chlorophenyl)amino)thiazole-4-carboxylate and Derivatives Are Potent Inducers of Oct3/4. J Med Chem. 2015 Aug 13;58(15):5742-50. doi: 10.1021/acs.jmedchem.5b00226. Epub 2015 Jul 23. PMID: 26143659.
In vitro protocol: 1. Gama-Brambila RA, Chen J, Zhou J, Tascher G, Münch C, Cheng X. A PROTAC targets splicing factor 3B1. Cell Chem Biol. 2021 May 11:S2451-9456(21)00211-7. doi: 10.1016/j.chembiol.2021.04.018. Epub ahead of print. PMID: 34048672. 2. Cheng X, Yoshida H, Raoofi D, Saleh S, Alborzinia H, Wenke F, Göhring A, Reuter S, Mah N, Fuchs H, Andrade-Navarro MA, Adjaye J, Gul S, Utikal J, Mrowka R, Wölfl S. Ethyl 2-((4-Chlorophenyl)amino)thiazole-4-carboxylate and Derivatives Are Potent Inducers of Oct3/4. J Med Chem. 2015 Aug 13;58(15):5742-50. doi: 10.1021/acs.jmedchem.5b00226. Epub 2015 Jul 23. PMID: 26143659.
In vivo protocol: TBD

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1: Cheng X, Yoshida H, Raoofi D, Saleh S, Alborzinia H, Wenke F, Göhring A,
Reuter S, Mah N, Fuchs H, Andrade-Navarro MA, Adjaye J, Gul S, Utikal J, Mrowka
R, Wölfl S. Ethyl 2-((4-Chlorophenyl)amino)thiazole-4-carboxylate and Derivatives
Are Potent Inducers of Oct3/4. J Med Chem. 2015 Aug 13;58(15):5742-50. doi:
10.1021/acs.jmedchem.5b00226. Epub 2015 Jul 23. PubMed PMID: 26143659.

O4I2

25.0mg / USD 150.0