Netropsin dihydrochloride

• CAT Number: M084937
• CAS Number: 18133-22-7
• Molecular Formula: C18H28Cl2N10O3
• Molecular Weight: 503.39
• Purity: ≥95%
• Synonyms: N-[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]-4-[[2-(diaminomethylideneamino)acetyl]amino]-1-methylpyrrole-2-carboxamide;dihydrochloride
• InChI: InChI=1S/C18H26N10O3.2ClH/c1-27-9-11(6-12(27)16(30)23-4-3-14(19)20)26-17(31)13-5-10(8-28(13)2)25-15(29)7-24-18(21)22;;/h5-6,8-9H,3-4,7H2,1-2H3,(H3,19,20)(H,23,30)(H,25,29)(H,26,31)(H4,21,22,24);2*1H
• InChIKey: SDRHUASONSRLFR-UHFFFAOYSA-N
• SMILES: CN1C=C(C=C1C(=O)NC2=CN(C(=C2)C(=O)NCCC(=N)N)C)NC(=O)CN=C(N)N.Cl.Cl

Netropsin dihydrochloride is a small-molecule MGB (minor-groove binder), inhibits the catalytic activity of isolated topoisomerase and interferes with the stabilization of the cleavable complexes of topoisomerase II and I in nuclei[1]. Netropsin dihydrochloride exhibits antiviral activity against the vaccinia virus[4].
Netropsin dihydrochloride has potential antibiotic and antiviral properties by binding to dsDNA in a non-intercalative manner, it improves survival from murine endotoxaemia by attenuating NOS2 induction through interference with HMGA1 DNA binding to the core NOS2 promoter[2].
Netropsin dihydrochloride in solutions of DNA has radioprotective ability against radiation-induced damage due to its high binding affinity and high structural stabilization, hydroxyl radical (OH*) generated by ionizing radiation cannot radiolyse the netropsin-DNA complex[3].

Reference

[1]. Beerman TA et al. Netropsin and bis-netropsin analogs as inhibitors of the catalytic activity of mammalian DNA topoisomerase II and topoisomerase cleavable complexes. Biochim Biophys Acta. 1991 Aug 27;1090(1):52-60.
 [Content Brief]

[2]. Grant MA, et al. Netropsin improves survival from endotoxaemia by disrupting HMGA1 binding to the NOS2 promoter. Biochem J. 2009 Feb 15;418(1):103-12.
 [Content Brief]

[3]. Mishra K et al. Netropsin, a minor groove binding ligand: a potential radioprotective agent. Radiat Res. 2009 Dec;172(6):698-705.
 [Content Brief]

[4]. Smee DF, et, al. A review of compounds exhibiting anti-orthopoxvirus activity in animal models. Antiviral Res. 2003 Jan;57(1-2):41-52.
 [Content Brief]