Oncrasin-1 | CAS#75629-57-1 | antitumor agent

MedKoo Cat#: 562886 | Name: Oncrasin-1

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Description:

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

Oncrasin-1 is an antitumor agent. Oncrasin-1 acts by inducing abnormal nuclear aggregation of PKC1 and suppressing RNA transcription. Oncrasin-1 was identified from a screen of KRAS mutant cancer cells and has shown specificity for KRAS mutant cell killing.

Chemical Structure

Oncrasin-1

CAS#75629-57-1

Theoretical Analysis

MedKoo Cat#: 562886

Name: Oncrasin-1

CAS#: 75629-57-1

Chemical Formula: C16H12ClNO

Exact Mass: 269.0607

Molecular Weight: 269.73

Elemental Analysis: C, 71.25; H, 4.48; Cl, 13.14; N, 5.19; O, 5.93

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 470.00
25mg	USD 860.00

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Synonym

Oncrasin-1; Oncrasin 1; Oncrasin1;

IUPAC/Chemical Name

1-(4-Chlorobenzyl)-1H-indole-3-carbaldehyde

InChi Key

ZDRQMXCSSAPUMM-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H12ClNO/c17-14-7-5-12(6-8-14)9-18-10-13(11-19)15-3-1-2-4-16(15)18/h1-8,10-11H,9H2

SMILES Code

O=CC1=CN(CC2=CC=C(Cl)C=C2)C3=C1C=CC=C3

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oncrasin-1 is an antitumor agent.

In vitro activity:

Results showed that oncrasin-1 treatment led to coaggregation of PKCiota and splicing factors into megaspliceosomes but had no obvious effects on the DNA repair molecule Rad51. Moreover, oncrasin-1 treatment suppressed the phosphorylation of the largest subunit of RNA polymerase II and the expression of intronless reporter genes in sensitive cells but not in resistant cells, suggesting that suppression of RNA transcription is a major effect of oncrasin-1 treatment. Studies with cultured cells or with recombinant proteins showed that oncrasin-1 can disrupt the interaction of PKCiota and cyclin-dependent protein kinase 9/cyclin T1 complex, which is known to phosphorylate the largest subunit of RNA polymerase II and is required for RNA transcription. Reference: J Med Chem. 2011 Apr 28;54(8):2668-79. https://pubmed.ncbi.nlm.nih.gov/19208825/

In vivo activity:

The results showed that, in comparison with solvent, oncrasin-1 suppressed tumor growth by 75.4% (Fig. 6A). Treatment with oncrasin-1 also prolonged survival (Fig. 6B): the mean survival times for mice treated with solvent and oncrasin-1 were 24 and 32, respectively. Reference: Cancer Res. 2008 Sep 15;68(18):7403-8. https://pubmed.ncbi.nlm.nih.gov/18794128/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	37.07
	DMSO	48.0	177.92
	DMSO:PBS (pH 7.2) (1:3)	0.3	0.93
	Ethanol	5.9	21.76

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 269.73 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. Wu S, Wang L, Guo W, Liu X, Liu J, Wei X, Fang B. Analogues and derivatives of oncrasin-1, a novel inhibitor of the C-terminal domain of RNA polymerase II and their antitumor activities. J Med Chem. 2011 Apr 28;54(8):2668-79. doi: 10.1021/jm101417n. Epub 2011 Apr 6. PMID: 21443218; PMCID: PMC3082393. 2. Guo W, Wu S, Wang L, Wang RY, Wei X, Liu J, Fang B. Interruption of RNA processing machinery by a small compound, 1-[(4-chlorophenyl)methyl]-1H-indole-3-carboxaldehyde (oncrasin-1). Mol Cancer Ther. 2009 Feb;8(2):441-8. doi: 10.1158/1535-7163.MCT-08-0839. Epub 2009 Feb 10. PMID: 19208825; PMCID: PMC2653085. 3. Guo W, Wu S, Liu J, Fang B. Identification of a small molecule with synthetic lethality for K-ras and protein kinase C iota. Cancer Res. 2008 Sep 15;68(18):7403-8. doi: 10.1158/0008-5472.CAN-08-1449. PMID: 18794128; PMCID: PMC2678915.

In vitro protocol:

In vivo protocol:

1. Guo W, Wu S, Liu J, Fang B. Identification of a small molecule with synthetic lethality for K-ras and protein kinase C iota. Cancer Res. 2008 Sep 15;68(18):7403-8. doi: 10.1158/0008-5472.CAN-08-1449. PMID: 18794128; PMCID: PMC2678915.

1: Dung DTM, Park EJ, Anh DT, Hai PT, Bao LQ, Ji AY, Kang JS, Tung TT, Han SB, Nam NH. Design, Synthesis and Evaluation of Novel (E)-N'-((1-(4-chlorobenzyl)-1H -indol-3-yl)methylene)-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides as Antitumor Agents. Anticancer Agents Med Chem. 2022;22(14):2586-2598. doi: 10.2174/1871520622666220118154914. PMID: 35040418. 2: McDonald AF, Goh YW, White JM, Scott AM, Ackermann U. Automated synthesis of 18F radiolabelled indole containing Oncrasin-like molecules; a comparison of iodonium salts and boronic ester chemistry. EJNMMI Radiopharm Chem. 2020 Nov 9;5(1):23. doi: 10.1186/s41181-020-00104-x. PMID: 33169204; PMCID: PMC7652984. 3: Singh M, Zhou X, Chen X, Santos GS, Peuget S, Cheng Q, Rihani A, Arnér ESJ, Hartman J, Selivanova G. Identification and targeting of selective vulnerability rendered by tamoxifen resistance. Breast Cancer Res. 2020 Jul 29;22(1):80. doi: 10.1186/s13058-020-01315-5. PMID: 32727562; PMCID: PMC7388523. 4: Peuget S, Zhu J, Sanz G, Singh M, Gaetani M, Chen X, Shi Y, Saei AA, Visnes T, Lindström MS, Rihani A, Moyano-Galceran L, Carlson JW, Hjerpe E, Joneborg U, Lehti K, Hartman J, Helleday T, Zubarev R, Selivanova G. Thermal Proteome Profiling Identifies Oxidative-Dependent Inhibition of the Transcription of Major Oncogenes as a New Therapeutic Mechanism for Select Anticancer Compounds. Cancer Res. 2020 Apr 1;80(7):1538-1550. doi: 10.1158/0008-5472.CAN-19-2069. Epub 2020 Feb 4. PMID: 32019870. 5: Gupta P, Dixit D, Sen E. Oncrasin targets the JNK-NF-κB axis to sensitize glioma cells to TNFα-induced apoptosis. Carcinogenesis. 2013 Feb;34(2):388-96. doi: 10.1093/carcin/bgs352. Epub 2012 Nov 3. PMID: 23125226. 6: Guo W, Wu S, Wang L, Wei X, Liu X, Wang J, Lu Z, Hollingshead M, Fang B. Antitumor activity of a novel oncrasin analogue is mediated by JNK activation and STAT3 inhibition. PLoS One. 2011;6(12):e28487. doi: 10.1371/journal.pone.0028487. Epub 2011 Dec 12. PMID: 22174819; PMCID: PMC3236185. 7: Wu S, Wang L, Guo W, Liu X, Liu J, Wei X, Fang B. Analogues and derivatives of oncrasin-1, a novel inhibitor of the C-terminal domain of RNA polymerase II and their antitumor activities. J Med Chem. 2011 Apr 28;54(8):2668-79. doi: 10.1021/jm101417n. Epub 2011 Apr 6. PMID: 21443218; PMCID: PMC3082393. 8: Wei X, Guo W, Wu S, Wang L, Huang P, Liu J, Fang B. Oxidative stress in NSC-741909-induced apoptosis of cancer cells. J Transl Med. 2010 Apr 16;8:37. doi: 10.1186/1479-5876-8-37. PMID: 20398386; PMCID: PMC2873373. 9: Guo W, Wu S, Wang L, Wang RY, Wei X, Liu J, Fang B. Interruption of RNA processing machinery by a small compound, 1-[(4-chlorophenyl)methyl]-1H-indole-3-carboxaldehyde (oncrasin-1). Mol Cancer Ther. 2009 Feb;8(2):441-8. doi: 10.1158/1535-7163.MCT-08-0839. Epub 2009 Feb 10. PMID: 19208825; PMCID: PMC2653085. 10: Guo W, Wu S, Liu J, Fang B. Identification of a small molecule with synthetic lethality for K-ras and protein kinase C iota. Cancer Res. 2008 Sep 15;68(18):7403-8. doi: 10.1158/0008-5472.CAN-08-1449. PMID: 18794128; PMCID: PMC2678915.