A 62176

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

MedKoo CAT#: 571173

CAS#: 148201-53-0

Description: A 62176 is a potent topoisomerase inhibitor. It exhibits antineoplastic activity by arresting the cell cycle in the G1 phase via the down-regulation of cyclin D1 and the up-regulation of p27(Kip1) in NCI-N87 gastric cancer cells.


Price and Availability

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A 62176 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#: 571173
Name: A 62176
CAS#: 148201-53-0
Chemical Formula: C20H17ClFN3O4
Exact Mass: 417.0892
Molecular Weight: 417.82
Elemental Analysis: C, 57.49; H, 4.10; Cl, 8.48; F, 4.55; N, 10.06; O, 15.32


Synonym: A 62176; A-62176; A62176

IUPAC/Chemical Name: 3H-Pyrido(3,2,1-kl)phenoxazine-2-carboxylic acid, 6-(2-amino-1-pyrrolidinyl)-5-fluoro-3-oxo-, monohydrochloride, (+-)-

InChi Key: VXQZSJYENUHWOD-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H16FN3O4.ClH/c21-12-8-10-16-19(17(12)23-7-3-6-15(23)22)28-14-5-2-1-4-13(14)24(16)9-11(18(10)25)20(26)27;/h1-2,4-5,8-9,15H,3,6-7,22H2,(H,26,27);1H

SMILES Code: O=C(C1=CN2C3=C(C(N4C(N)CCC4)=C(F)C=C3C1=O)OC5=CC=CC=C25)O.[H]Cl


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).

Harmonized System Code:
293490


References

1: Kim HL, Jeon KH, Jun KY, Choi Y, Kim DK, Na Y, Kwon Y. A-62176, a potent topoisomerase inhibitor, inhibits the expression of human epidermal growth factor receptor 2. Cancer Lett. 2012 Dec 1;325(1):72-9. doi: 10.1016/j.canlet.2012.06.004. Epub 2012 Jun 23. PubMed PMID: 22732416.

2: Yu H, Kwok Y, Hurley LH, Kerwin SM. Efficient, Mg(2+)-dependent photochemical DNA cleavage by the antitumor quinobenzoxazine (S)-A-62176. Biochemistry. 2000 Aug 22;39(33):10236-46. PubMed PMID: 10956013.

3: Fan JY, Sun D, Yu H, Kerwin SM, Hurley LH. Self-assembly of a quinobenzoxazine-Mg2+ complex on DNA: a new paradigm for the structure of a drug-DNA complex and implications for the structure of the quinolone bacterial gyrase-DNA complex. J Med Chem. 1995 Feb 3;38(3):408-24. PubMed PMID: 7853333.

4: Kwok Y, Zeng Q, Hurley LH. Structural insight into a quinolone-topoisomerase II-DNA complex. Further evidence for a 2:2 quinobenzoxazine-mg2+ self-assembly model formed in the presence of topoisomerase ii. J Biol Chem. 1999 Jun 11;274(24):17226-35. PubMed PMID: 10358081.

5: Kwok Y, Sun D, Clement JJ, Hurley LH. The quinobenzoxazines: relationship between DNA binding and biological activity. Anticancer Drug Des. 1999 Oct;14(5):443-50. PubMed PMID: 10766299.

6: Kang DH, Kim JS, Jung MJ, Lee ES, Jahng Y, Kwon Y, Na Y. New insight for fluoroquinophenoxazine derivatives as possibly new potent topoisomerase I inhibitor. Bioorg Med Chem Lett. 2008 Feb 15;18(4):1520-4. doi: 10.1016/j.bmcl.2007.12.053. Epub 2007 Dec 25. PubMed PMID: 18178085.

7: Kwon Y, Na Y. Study on the synthesis and cytotoxicity of new quinophenoxazine derivatives. Chem Pharm Bull (Tokyo). 2006 Feb;54(2):248-51. PubMed PMID: 16462076.

8: Permana PA, Snapka RM, Shen LL, Chu DT, Clement JJ, Plattner JJ. Quinobenoxazines: a class of novel antitumor quinolones and potent mammalian DNA topoisomerase II catalytic inhibitors. Biochemistry. 1994 Sep 20;33(37):11333-9. PubMed PMID: 7727384.

9: Kim MY, Na Y, Vankayalapati H, Gleason-Guzman M, Hurley LH. Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents. J Med Chem. 2003 Jul 3;46(14):2958-72. PubMed PMID: 12825936.