{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 416422024 | ImageFile =Netropsin.png | ImageClass = skin-invert-image | IUPACName = N-{5-[(3-Amino-3-iminopropyl)carbamoyl]-1-methyl-1H-pyrrol-3-yl}-4-[(N-carbamimidoylglycyl)amino]-1-methyl-1H-pyrrole-2-carboxamide | OtherNames = Nt, congocidin, sinanomycin | Section1 = {{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 1438-30-8 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 64B3O0RD7N | PubChem = 4461 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 553984 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4306 | SMILES = [H]/N=C(/CCNC(=O)c1cc(cn1C)NC(=O)c2cc(cn2C)NC(=O)CN=C(N)N)\N | InChI = 1/C18H26N10O3/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) | InChIKey = IDBIFFKSXLYUOT-UHFFFAOYAW | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C18H26N10O3/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) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = IDBIFFKSXLYUOT-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties | Formula = C<sub>18</sub>H<sub>26</sub>N<sub>10</sub>O<sub>3</sub> · 2HCl | MolarMass = 503.39 g/mol | Appearance = White powder }} }} '''Netropsin''' (also termed '''congocidine''' or '''sinanomycin'''<ref>[http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/N9653 Netropsin dihydrochloride] at [[Sigma-Aldrich]]</ref>) is a [[polyamide]] with [[antibiotic]] and [[Antiviral drug|antiviral]] activity. Netropsin was discovered by Finlay ''et al.'', and first isolated from the [[Actinomycetota|actinobacterium]] ''[[Streptomyces netropsis]]''.<ref>A.C. Finlay, F. A. Hochstein, B. A. Sobin, and F. X. Murphy, ''J. Am. Chem Soc.'' '''73''' 341-343 (1951)</ref> It belongs to the class of pyrrole-amidine [[antibiotics]].
== DNA binding properties == Netropsin binds to the [[minor groove]] of AT-rich sequences of double stranded [[DNA]].<ref>C. Zimmer and U. Wähnert, ''Prog. Biophys. Molec. Biol.'' '''47''' 31-112 (1986)</ref> In contrast, netropsin does not bind single stranded DNA or double stranded RNA. Crystallographic structures of DNA-bound Netropsin have been obtained and elucidate details of how the drug binds in the minor groove.<ref>M. L. Kopka, C. Yoon, D. Goodsell, P. Pjura, and R.E. Dickerson, ''J. Mol. Biol.'' '''183''' 553-563 (1985)</ref><ref>M. L. Kopka, C. Yoon, D. Goodsell, P. Pjura, and R.E. Dickerson, ''Proc. Natl. Acad. Sci. USA'' '''82''' 1376-1380 (1985)</ref> In the bound structure, the drug makes hydrogen bonding interactions with four subsequent base pairs of the DNA duplex, locally displacing the water molecules of the spine of hydration.
[[Image:Netropsin DNA bound.gif|thumb|right|150px|Netropsin (shown in space-filling representation) bound to DNA (shown as bonds)]]
Using gel mobility and analytical ultracentrifugation, it was shown that Netropsin binding to DNA increases the twist per base by similar to 9˚ per molecule bound.<ref>G. Snounou and A. D. B. Malcolm, ''J. Mol. Biol.'' '''167''' 211-216 (1983)</ref><ref>H. Triebel, H. Bär, R. Geuther, and G. Burckhardt, ''Progr. Colloid. Polym. Sci.'' '''99''' 45-54 (1995)</ref> Thus, it removes supercoils when interacting with positively supercoiled DNA and introduces (additional) negative supercoils when binding to relaxed or negatively supercoiled DNA. Netropsin's effect on supercoiled DNA was observed in detail on single molecules using a magnetic tweezers.<ref>J. Lipfert, S. Klijnhout, and Nynke H. Dekker, "Nucleic Acids Res." "38" 7122-32 (2010)</ref>
== Antibiotic properties == It has been shown that Netropsin is active both against [[Gram-positive bacteria]] and [[Gram-negative bacteria]].<ref>C. Zimmer and U. Wähnert, ''Prog. Biophys. Molec. Biol.'' '''47''' 31-112 (1986)</ref>
== See also == * [[Lexitropsin]] * [[Hoechst 33258]] * [[DAPI]] * [[Pentamidine]] * [[DNA-binding protein]] * [[Single-strand binding protein]] * [[Comparison of nucleic acid simulation software]]
== References == {{Reflist}}
[[Category:Amidines]] [[Category:Guanidines]] [[Category:Antibiotics]] [[Category:DNA-binding substances]] [[Category:Imidazoles]]