Netropsin dihydrochloride

A DNA minor groove binder

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1mg

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Background

Netropsin is a DNA minor groove binder originally isolated from S. netropsis.^1,2 It binds to A/T rich regions of DNA (K_a = 4.9 x 10⁵ M^-1 for poly(dA)poly(dT) DNA).³ Netropsin inhibits topoisomerase II (IC₉₀ = 200 ?M in a cell-free assay) and teniposide-induced crosslinks in nuclei from 935.1 mouse fibrosarcoma cells (IC₅₀ = 65 ?M).⁴ It is active against several bacteria, including S. aureus, S. typhosa, K. pneumoniae, and A. aerogenes with MIC values of 5, 10, 10, and 5 ?g/ml, respectively.² Netropsin (75 ?g/ml) inhibits viral plaque formation in Shope fibroma virus- or vaccinia virus-infected BS-C-1 host cells.⁵ It increases survival in a mouse model of endotoxemia induced by LPS when administered at a dose of 25 mg/kg.⁶

1.Neidle, S.DNA minor-groove recognition by small moleculesNat. Prod. Rep.18(3)291-309(2001) 2.Finlay, A.C., Hochstein, F.A., Sobin, B.A., et al.Netropsin, a new antibiotic produced by a StreptomycesJ. Am. Chem. Soc.73(1)341-343(1951) 3.Wartell, R.M., Larson, J.E., and Wells, R.D.Netropsin. A specific probe for A-T regions of duplex deoxyribonucleic acidJ. Biol. Chem.249(21)6719-6731(1974) 4.Beerman, T.A., Woynarowski, J.M., Sigmund, R.D., et al.Netropsin and bis-netropsin analogs as inhibitors of the catalytic activity of mammalian DNA topoisomerase II and topoisomerase cleavable complexesBiochim. Biophys. Acta1090(1)52-60(1991) 5.Becker, Y., Asher, Y., and Zakay-Rones, Z.Congocidine and distamycin A, antipoxvirus antibioticsAntimicrob. Agents Chemother.1(6)483-488(1972) 6.Grant, M.A., Baron, R.M., Macias, A.A., et al.Netropsin improves survival from endotoxaemia by disrupting HMGA1 binding to the NOS2 promoterBiochem. J.418(1)103-112(2009)