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.


Chemical Structure

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A 62176
CAS# 148201-53-0

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

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 417.82 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.

Recalculate based on batch purity %
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

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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.