Related CAS #
468719-52-0 (free base)
1350966-83-4 (mesylate 1:1)
468719-53-1 (mesylate 1:3)
1523457-12-6 (HBr 1:1)
468719-51-9 (HBr 1:3)
Synonym
AFP464; AFP 464; AFP-464; AFP-464 mesylate
IUPAC/Chemical Name
(2S)-2,6-diamino-N-[4-(5-amino-6,8-difluoro-7-methyl-4-oxochromen-2-yl)-2-fluorophenyl]hexanamide
InChi Key
WHWJKUICJXPKFQ-ZDUSSCGKSA-N
InChi Code
InChI=1S/C22H23F3N4O3/c1-10-18(24)20(28)17-15(30)9-16(32-21(17)19(10)25)11-5-6-14(12(23)8-11)29-22(31)13(27)4-2-3-7-26/h5-6,8-9,13H,2-4,7,26-28H2,1H3,(H,29,31)/t13-/m0/s1
SMILES Code
O=C(NC1=CC=C(C2=CC(C3=C(O2)C(F)=C(C)C(F)=C3N)=O)C=C1F)[C@@H](N)CCCCN
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, not in water
Shelf Life
>5 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
According to http://www.tigrispharma.com/afp464.html, AFP-464, a lysyl pro-drug of aminoflavone (AF), is synthesized to improve the aqueous solubility of the parent compound AF. AFP-464 undergoes rapid conversion to AF in plasma by nonspecific plasma esterases. AF is an investigational anticancer agent with a unique pattern of growth inhibitory activity in the NCI 60 tumor cell line screen (COMPARE analysis; http://www.dtp.nci.nih.gov), suggesting a novel mechanism of action. Human tumor cell lines that exhibited particular sensitivity to AF included those of breast and renal origin. In vivo antitumor activity of AF was demonstrated in several xenograft studies in mice bearing A-498, CaKi-1 renal and MCF-7 breast cancer. Previous studies with human breast and renal cancer cell lines showed that AF induced CYP1A1/1A2 and CYP1B1 protein expression and was converted to metabolites that were covalently bound to DNA. This resulted in phosphorylation of p53 with induction of the p53 downstream target p21Waf1/Cip1 and apotosis.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
448.45
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. Kuffel MJ, Schroeder JC, Pobst LJ, et al., Activation of the antitumor agent aminoflavone (NSC 686288) is mediated by induction of tumor cell cytochrome P450 1A1/1A2. Mol Pharmacol 2002:62:143-153.
2. Loaiza-Perez AI, Kenney S, Boswell J, et al., Sensitivity of renal cell carcinoma to aminoflavone: Role of CYP1A1. The Journal of Urology 2004:171:1688-1697.
3. Loaiza-Perez AI, Kenney S, Boswell J, et al., Aryl hydrocarbon receptor activation of an antitumor aminoflavone: Basis of selective toxicity for MCF-7 breast tumor cells. Mol Cancer Therapeutics 2004:3(6):715-725.
4. Meng L, Kohlhagen G, Liao Z, et al., DNA-protein cross-links and replication-dependent histone H2AX phosphorylation induced by aminoflavone (NSC 686288), a novel anticancer agent active against human breast cancer cells. Cancer Res 2005:65(12):5337-43.
5. Pobst LJ, Ames MM, et al., CYP1A1 activation of aminoflavone leads to DNA damage in human tumor cell lines. Cancer Chemother Pharmacol 2005.
