O4I2 | CAS#165682-93-9 | inducers of Oct3/4

MedKoo Cat#: 522505 | Name: O4I2

Description:

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

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

O4I2

CAS#165682-93-9

Theoretical Analysis

MedKoo Cat#: 522505

Name: O4I2

CAS#: 165682-93-9

Chemical Formula: C12H11ClN2O2S

Exact Mass: 282.0230

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

Size	Price	Availability
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 650.00	Ready to ship
500mg	USD 1,450.00	Ready to ship
1g	USD 2,450.00	Ready to ship
2g	USD 3,850.00	Ready to ship
5g	USD 5,850.00	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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#CRB60223

QC Data

View QC data: current batch, Lot#CRB60223

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	70.70

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 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.

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:

In vivo protocol:

TBD

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.