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
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.
| 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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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.
