Topovale | ARC-111 | CAS#500214-53-9 | topoisomerase I inhibitor

MedKoo Cat#: 407363 | Name: Topovale

Description:

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

Topovale, also known as ARC-111, is a potent topoisomerase I inhibitor. ARC-111 inhibits hypoxia-mediated hypoxia-inducible factor-1alpha accumulation. ,ARC-111 exhibited low nM cytotoxicity against a panel of cancer cells. ARC-111 cytotoxicity as well as ARC-111-induced apoptosis was reduced >100-fold in CPT-resistant topoisomerase I (TOP1)-deficient P388/CPT45 cells as compared with P388 cells.

Chemical Structure

Topovale

CAS#500214-53-9

Theoretical Analysis

MedKoo Cat#: 407363

Name: Topovale

CAS#: 500214-53-9

Chemical Formula: C23H23N3O5

Exact Mass: 421.1638

Molecular Weight: 421.45

Elemental Analysis: C, 65.55; H, 5.50; N, 9.97; O, 18.98

Price and Availability

Size	Price	Availability
25mg	USD 550.00	2 Weeks
50mg	USD 950.00	2 Weeks
100mg	USD 1,650.00	2 Weeks
200mg	USD 2,450.00	2 Weeks
500mg	USD 3,650.00	2 Weeks
1g	USD 4,950.00	2 Weeks
2g	USD 8,950.00	2 Weeks

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Related CAS #

No Data

Synonym

Topovale; Topoval; ARC 111; ARC111; ARC-111.

IUPAC/Chemical Name

12-(2-(dimethylamino)ethyl)-2,3-dimethoxy-[1,3]dioxolo[4',5':4,5]benzo[1,2-h]benzo[c][1,6]naphthyridin-13(12H)-one

InChi Key

UVXCXZBZPFCAAJ-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H23N3O5/c1-25(2)5-6-26-22-15-9-20-21(31-12-30-20)10-17(15)24-11-16(22)13-7-18(28-3)19(29-4)8-14(13)23(26)27/h7-11H,5-6,12H2,1-4H3

SMILES Code

COC1=C(OC)C=C(C(N(CCN(C)C)C2=C3C=NC4=C2C=C(OCO5)C5=C4)=O)C3=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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 421.45 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

1: Zhou W, Dai Z, Chen Y, Wang H, Yuan Z. High-Dimensional descriptor selection and computational QSAR modeling for antitumor activity of ARC-111 analogues Based on Support Vector Regression (SVR). Int J Mol Sci. 2012;13(1):1161-72. doi: 10.3390/ijms13011161. PubMed PMID: 22312310; PubMed Central PMCID: PMC3269744. 2: Li TK, Houghton PJ, Desai SD, Daroui P, Liu AA, Hars ES, Ruchelman AL, LaVoie EJ, Liu LF. Characterization of ARC-111 as a novel topoisomerase I-targeting anticancer drug. Cancer Res. 2003 Dec 1;63(23):8400-7. PubMed PMID: 14679002. 3: Feng W, Satyanarayana M, Tsai YC, Liu AA, Liu LF, LaVoie EJ. Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c ,h][1,6]naphthyridin-6-one iodide. Eur J Med Chem. 2009 Sep;44(9):3433-8. doi: 10.1016/j.ejmech.2009.02.004. PubMed PMID: 19299037; PubMed Central PMCID: PMC2766012. 4: Kurtzberg LS, Battle T, Rouleau C, Bagley RG, Agata N, Yao M, Schmid S, Roth S, Crawford J, Krumbholz R, Ewesuedo R, Yu XJ, Wang F, Lavoie EJ, Teicher BA. Bone marrow and tumor cell colony-forming units and human tumor xenograft efficacy of noncamptothecin and camptothecin topoisomerase I inhibitors. Mol Cancer Ther. 2008 Oct;7(10):3212-22. doi: 10.1158/1535-7163.MCT-08-0568. PubMed PMID: 18852125. 5: Feng W, Satyanarayana M, Tsai YC, Liu AA, Liu LF, Lavoie EJ. Facile formation of hydrophilic derivatives of 5H-8,9-dimethoxy-5-[2-(N,N-dimethylamino)ethyl]-2,3-methylenedioxydibenzo[c,h] [1,6]naphthyridin-6-one (ARC-111) and its 12-aza analog via quaternary ammonium intermediates. Bioorg Med Chem Lett. 2008 Jun 15;18(12):3570-2. doi: 10.1016/j.bmcl.2008.05.005. PubMed PMID: 18511275. 6: Meng F, Nguyen XT, Cai X, Duan J, Matteucci M, Hart CP. ARC-111 inhibits hypoxia-mediated hypoxia-inducible factor-1alpha accumulation. Anticancer Drugs. 2007 Apr;18(4):435-45. PubMed PMID: 17351396. 7: Ruchelman AL, Houghton PJ, Zhou N, Liu A, Liu LF, LaVoie EJ. 5-(2-aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: variation of n-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance. J Med Chem. 2005 Feb 10;48(3):792-804. PubMed PMID: 15689163. 8: Ruchelman AL, Zhu S, Zhou N, Liu A, Liu LF, LaVoie EJ. Dimethoxybenzo[i]phenanthridine-12-carboxylic acid derivatives and 6H-dibenzo[c,h][2,6]naphthyridin-5-ones with potent topoisomerase I-targeting activity and cytotoxicity. Bioorg Med Chem Lett. 2004 Nov 15;14(22):5585-9. PubMed PMID: 15482929. 9: Zhu S, Ruchelman AL, Zhou N, Liu AA, Liu LF, LaVoie EJ. Esters and amides of 2,3-dimethoxy-8,9-methylenedioxy-benzo[i]phenanthridine-12-carboxylic acid: potent cytotoxic and topoisomerase I-targeting agents. Bioorg Med Chem. 2005 Dec 15;13(24):6782-94. PubMed PMID: 16153852.