69408-81-7

Basic information

• Product Name: Amonafide
• Synonyms: AMONAFIDE DIHYDROCHLORIDE,1H-BENZ[DE]ISOQUINOLINE-1,3(2H)-DIONE, 5-AMINO-2-[2-(DIMETHYLAMINO)ETHYL]-;AMONAFIDE;1H-Benz[de]isoquinoline-1,3(2H)-dione, 5-amino-2-[2-(dimethylamino)ethyl]-;5-Amino-2-[2-(dimethylamino)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione;FA-142;MFA-142;Nafidimide;NSC-308847
• CAS NO: 69408-81-7
• Molecular Formula: C₁₆H₁₇N₃O₂
• Molecular Weight: 283.32
• Product Categories: Amines;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 69408-81-7.mol
• Article Data: 20

Chemical Properties

• Melting Point: 162-164°C
• Boiling Point: 500.2 °C at 760 mmHg
• Flash Point: 256.3 °C
• Appearance: /
• Density: 1.306 g/cm³
• Vapor Pressure: 3.89E-10mmHg at 25°C
• Refractive Index: 1.681
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.83±0.28(Predicted)
• CAS DataBase Reference: Amonafide(CAS DataBase Reference)
• NIST Chemistry Reference: Amonafide(69408-81-7)
• EPA Substance Registry System: Amonafide(69408-81-7)

Safety Data

• Hazardous Substances Data: 69408-81-7(Hazardous Substances Data)

Usage

Uses

Amonafide is a DNA intercalator and topoisomerase II inhibitor in clinical development for the treatment of neoplastic diseases. Antitumor agent.

Biological Activity

amonafide is a novel topoisomerase ii inhibitor. topoisomerase ii plays critical roles including dna transcription, replication and chromosome segregation. though the biological functions of topoisomerase ii are important for insuring genomic integrity, the ability to interfere with topoisomerase ii and generate enzyme mediated dna damage is an effective strategy for cancer chemotherapy.

in vitro

amonafide intercalated with dna and disrupted the loading of topoisomerases. in contrast to the classic agents, amonafide was found to induce higher molecular weight fragmentation, resulting in the apoptosis without dna cleavage. amonafide was found to act in an atp-independent manner and seemed unlikely to induce the chromosome translocations associated with treatmentinduced leukemia [1].

in vivo

amonafide was found to be able to inhibit ip l1210 leukemia, with optimal increased life spans (ils) of 61% to 106% following single 16 mg/kg dosing on days 1 to 9. similar efficacy was noted against ip p388 murine leukemia and the sc implanted l1210 leukemia. additionally, amonafide demonstrated activity against two nonleukemic ip implanted murine tumors, the m5076 sarcoma and the b16 melanoma [2].

IC 50

4.67, 2.73, and 6.38 for ht-29, hela, and pc3 cells, respectively

references

[1] freeman cl,swords r,giles fj. amonafide: a future in treatment of resistant and secondary acute myeloid leukemia expert rev hematol.2012 feb;5(1):17-26. [2] saez r,craig jb,kuhn jg,weiss gr,koeller j,phillips j,havlin k,harman g,hardy j,melink tj, et al. phase i clinical investigation of amonafide. j clin oncol.1989 sep;7(9):1351-8.

InChI:InChI=1/C16H17N3O2/c1-18(2)6-7-19-15(20)12-5-3-4-10-8-11(17)9-13(14(10)12)16(19)21/h3-5,8-9H,6-7,17H2,1-2H3

Upstream product

• 3027-38-1 3-nitro-1,8-naphthalic anhydride 
• 81-84-5 1,8-Naphthalic anhydride 
• 108-00-9 N,N-dimethylethylenediamine 
• 54824-17-8 mitonafide 
• 23204-38-8 3-amino-naphthalene-1,8-dicarboxylic acid-anhydride 

Downstream Products

• 868962-44-1 2-[2-(dimethylamino)ethyl]-5-{[(1Z)-(2,5-dihydroxyphenyl)methylene]amino}-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 868962-66-7 5-{[(1Z)-benzo-(3,5-bis(acetoxy)-2-[(acetoxy)methyl]-6-oxy-tetrahydro-2H-pyran-4-ylacetate)-5-ylmethylene]amino}-N-(2-[2-(dimethylamino)ethyl]-1H-benzo[de]isoquinolin-1,3(2H)-dione) 
• 69409-02-5 2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5-ylacetamide 
• 1358552-78-9 2-[2-(dimethylamino)ethyl]-5-[(4-methoxylphenyl)amino]-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 1358552-81-4 2-[2-(dimethylamino)ethyl]-5-[(4-nitrophenyl)amino]-1H-benzo[de]isoquinoline-1,3(2H)-dione 

Relevant articles and documents

Real-Time Multi-Photon Tracking and Bioimaging of Glycosylated Theranostic Prodrugs upon Specific Enzyme Triggered Release

Real-time tracking of prodrug uptake, delivery and activation in vivo represents a major challenge for prodrug development. Herein, we demonstrate the use of novel glycosylated theranostics of the cancer pharmacophore Amonafide in highly-selective, enzyma

Fluorescent probe for detecting tiredness level Preparation method and application thereof

The invention discloses a fluorescence probe for detecting the level of hypoxia, a preparation method and application thereof, and can realize specific response Na. 2 S2 O4 The fluorescence probe is used for detecting the tiredness level, and the structure is as follows. The probe comprises a nitrogen-nitrogen double bond, which can be broken down in a hypoxic environment to cause fluorescence recovery of the compound. The naphthalimide is introduced as a fluorophore, and has the characteristics of stable fluorescence and high fluorescence quantum efficiency. The fluorescent probe is simple and convenient to prepare, obvious in spectral change, good in specificity effect, small in cytotoxicity, good in imaging effect and good in specificity detection Na. 2 S2 O4 , The fluorophore precursor and the anti-tumor drug nitrogen mustard compound can be released under the hypoxic condition, the tumor cell growth can be inhibited while the hypoxia imaging is carried out, the diagnosis and treatment integrated function is achieved, and the application prospect is good.

Hydrogen sulfide triggered molecular agent for imaging and cancer therapy

We developed an activatable molecular reagent, PNF, triggered by intracellular H2S in the lysosome to release the therapeutic drug amonafide, which can escape from the lysosome into the nucleus to induce autophagy of cancer cells. PNF exhibits potent inhibitory activity against cisplatin-resistant tumor cell lines.