NC190 sodium

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MedKoo CAT#: 591665

CAS#: 120602-99-5

Description: NC190 is a topoisomerase II-inhibitor that inhibited the growth of FM3A cells in clinical trials. NC-190 strongly inhibited the growth of FM3A cells with an IC50 of 0.019 microg/ml (0.042 microM) when cultured with NC-190 for 48 h. NC-190 potently suppressed DNA synthesis, with 90% inhibition observed at 0.1 microg/ml of NC-190.


Price and Availability

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Pricing updated 2020-08-08. Prices are subject to change without notice.

NC190 sodium is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 591665
Name: NC190 sodium
CAS#: 120602-99-5
Chemical Formula: C23H21N4NaO5
Exact Mass:
Molecular Weight: 456.43
Elemental Analysis: C, 60.52; H, 4.64; N, 12.28; Na, 5.04; O, 17.53


Synonym: NC190; NC-190; NC 190

IUPAC/Chemical Name: Sodium 6-((2-(dimethylamino)ethyl)carbamoyl)-5-hydroxy-10-methoxybenzo[a]phenazine-9-carboxylate

InChi Key: GHPJVVCCBMRQAR-UHFFFAOYSA-M

InChi Code: InChI=1S/C23H22N4O5.Na/c1-27(2)9-8-24-22(29)18-20-19(12-6-4-5-7-13(12)21(18)28)25-16-11-17(32-3)14(23(30)31)10-15(16)26-20;/h4-7,10-11,28H,8-9H2,1-3H3,(H,24,29)(H,30,31);/q;+1/p-1

SMILES Code: O=C(C1=C(OC)C=C2C(N=C3C(C(NCCN(C)C)=O)=C(O)C4=CC=CC=C4C3=N2)=C1)[O-].[Na+]


Technical Data

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


Additional Information

Although NC-190 did not directly inhibit the activitiy of thymidine kinase in a cell-free system, expression of mRNA of thymidine kinase was suppressed by 75% in NC-190-treated cells. These results indicate that NC-190 can suppress the expression of the gene for thymidine kinase and the inhibition of thymidine kinase contributes to the inhibition of cell growth by NC-190 together with the inhibition of topoisomerase II. (https://www.ncbi.nlm.nih.gov/pubmed/14632316)


References

1: Moorthy NS, Pratheepa V, Ramos MJ, Vasconcelos V, Fernandes PA. Fused aryl-phenazines: scaffold for the development of bioactive molecules. Curr Drug Targets. 2014;15(7):681-8. Review. PubMed PMID: 24499398.

2: Gibbs JF, Rustum YM, Slocum HK. Image analysis using the fluorochromasia assay to quantify tumor drug sensitivity. Methods Mol Med. 2005;110:185-95. PubMed PMID: 15901936.

3: Samata K, Yamagishi T, Ikeda T, Kuraishi A, Nakaike S, Tanaka M, Kashiwagi K, Igarashi K. The topoisomerase II-inhibitor NC-190 reduces the level of thymidine kinase mRNA in murine tumor cells. Res Commun Mol Pathol Pharmacol. 2002;111(1-4):77-87. PubMed PMID: 14632316.

4: Samata K, Yamagishi T, Ichihara T, Nanaumi K, Ikeda T, Ikeya H, Kuraishi A, Nakaike S, Kashiwagi K, Igarashi K. Establishment and characterization of a mouse FM3A cell mutant resistant to topoisomerase II-inhibitor NC-190. Cancer Chemother Pharmacol. 2002 Nov;50(5):367-72. Epub 2002 Sep 5. PubMed PMID: 12439594.

5: Yamagishi T, Nakaike S, Ikeda T, Ikeya H, Otomo S. A novel antitumor compound, NC-190, induces topoisomerase II-dependent DNA cleavage and DNA fragmentation. Cancer Chemother Pharmacol. 1996;38(1):29-34. PubMed PMID: 8603448.

6: Furue H. [Topoisomerase inhibitors developing in Japan]. Gan To Kagaku Ryoho. 1993 Jan;20(1):42-9. Review. Japanese. PubMed PMID: 8422186.

7: Yamagishi T, Nakaike S, Nanaumi K, Otomo S, Tsukagoshi S. The effect of NC-190, a novel antitumor compound, on the cell-cycle progression of HeLa S3 cells. Cancer Chemother Pharmacol. 1993;32(4):249-54. PubMed PMID: 8324865.

8: Sugiura T, Ariyoshi Y. [DNA topoisomerase inhibitor]. Gan To Kagaku Ryoho. 1992 Nov;19(13):2140-5. Review. Japanese. PubMed PMID: 1332623.

9: Nakaike S, Yamagishi T, Nanaumi K, Otomo S, Tsukagoshi S. Cell-killing activity and kinetic analysis of a novel antitumor compound NC-190, a benzo[a]phenazine derivative. Jpn J Cancer Res. 1992 Apr;83(4):402-9. PubMed PMID: 1506275; PubMed Central PMCID: PMC5918839.

10: Ebina T, Shishido K, Murata K. [Antitumor effect of a novel antitumor compound, NC-190, in the double grafted tumor system]. Gan To Kagaku Ryoho. 1990 Jul;17(7):1345-50. Japanese. PubMed PMID: 2369138.

11: Tsuruo T, Naito M, Takamori R, Tsukahara S, Yamabe-Mitsuhashi J, Yamazaki A, Oh-hara T, Sudo Y, Nakaike S, Yamagishi T. A benzophenazine derivative, N-beta-dimethylaminoethyl 9-carboxy-5-hydroxy-10-methoxy-benzo[a]phenazine-6-carboxamide, as a new antitumor agent against multidrug-resistant and sensitive tumors. Cancer Chemother Pharmacol. 1990;26(2):83-7. PubMed PMID: 2161296.

12: Nakaike S, Yamagishi T, Samata K, Nishida K, Inazuki K, Ichihara T, Migita Y, Otomo S, Aihara H, Tsukagoshi S. In vivo activity on murine tumors of a novel antitumor compound, N-beta-dimethylaminoethyl 9-carboxy-5-hydroxy-10-methoxybenzo[a]phenazine-6-carboxamide sodium salt (NC-190). Cancer Chemother Pharmacol. 1989;23(3):135-9. PubMed PMID: 2924370.