Mitonafide

• CAT Number: R051029
• CAS Number: 54824-17-8
• Molecular Formula: C16H15N3O4
• Molecular Weight: 313.31
• Purity: ≥95%
• Synonyms: 2-[2-(dimethylamino)ethyl]-5-nitrobenzo[de]isoquinoline-1,3-dione
• InChI: InChI=1S/C16H15N3O4/c1-17(2)6-7-18-15(20)12-5-3-4-10-8-11(19(22)23)9-13(14(10)12)16(18)21/h3-5,8-9H,6-7H2,1-2H3
• InChIKey: XXVLKDRPHSFIIB-UHFFFAOYSA-N
• SMILES: CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(=C32)C1=O)[N+](=O)[O-]

Mitonafide (NSC 300288) is a cytostatic agent. Mitonafide binds to double-stranded DNA through intercalation, and inhibits DNA and RNA synthesis. Mitonafide is an antitumor agent that can be used in the research of cancers, such as non-small cell lung cancer (NSCLC), leukemia[1][2][3].
Mitonafide inhibits DNA and RNA synthesis and induces single-strand breaks in the DNA of chinese hamster ovary cells[1].
The incubation of Mitonafide with rat liver microsomes and NADPH under anaerobic conditions results in the formation of a metabolite identified as 5-aminomitonafide[2].
Mitonafide (25, 50 μM, 1 h) induces single-stand breaks in the DNA of L1210 cells[2].
Mitonafide (10-100 μM) exhibits cytotoxic effect in the HOP-62 lung cell line[4].
Mitonafide (0.5 and 1 mg/kg, i.p., 1-7 days) shows antitumoral potency in S-180 bearing mice[4].
Mitonafide (5 mg/kg, i.p., twice a day) shows anticancer activity in HepG2 xenograft model[6].
Mitonafide (single i.p. injection, S-180 bearing mice) shows the LD50 value of 10.0 mg/kg[5].

Reference

[1]. Llombart M, et al. Phase I study of mitonafide in solid tumors. Invest New Drugs. 1992 Aug;10(3):177-81.
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[2]. inha BK, et al. Mechanism of DNA strand breaks by mitonafide, an imide derivative of 3-nitro-1,8-naphthalic acid. Biochem Pharmacol. 1985 Nov 1;34(21):3845-52.
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[3]. Rosell R, et al. Phase I study of mitonafide in 120 hour continuous infusion in non-small cell lung cancer. Invest New Drugs. 1992 Aug;10(3):171-5.
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[4]. Samanta S, et al. Antitumor activity of Nitronaphthal-NU, a novel mixed-function agent. J Exp Ther Oncol. 2005;5(1):15-22.
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[5]. Pain A, et al. Evaluation of naphthalmustine, a nitrogen mustard derivative of naphthalimide as a rationally-designed anticancer agent. J Exp Clin Cancer Res. 2003 Sep;22(3):411-8.
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[6]. Xin M, et al. Design, synthesis and biological evaluation of 3-nitro-1,8-naphthalimides as potential antitumor agents. Bioorg Med Chem Lett. 2020 Apr 15;30(8):127051.
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