Netropsin

Netropsin

Names
IUPAC name N-{5-[(3-Amino-3-iminopropyl)carbamoyl]-1-methyl-1H-pyrrol-3-yl}-4-[(N-carbamimidoylglycyl)amino]-1-methyl-1H-pyrrole-2-carboxamide
Other names Nt, congocidin, sinanomycin
Identifiers
CAS Number	1438-30-8 Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL553984 N
ChemSpider	4306 N
ECHA InfoCard	100.162.288
PubChem	4461
InChI InChI=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) N Key: IDBIFFKSXLYUOT-UHFFFAOYSA-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) Key: IDBIFFKSXLYUOT-UHFFFAOYAW
SMILES [H]/N=C(/CCNC(=O)c1cc(cn1C)NC(=O)c2cc(cn2C)NC(=O)CN=C(N)N)\N
Properties
Chemical formula	C18H26N10O3 · 2HCl
Molar mass	503.39 g/mol
Appearance	White powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Netropsin (also termed congocidine or sinanomycin) is a polyamide with antibiotic and antiviral activity. Netropsin was discovered by Finlay et al., and first isolated from the actinobacterium Streptomyces netropsis. It belongs to the class of pyrrole-amidine antibiotics.

Netropsin binds to the minor groove of AT-rich sequences of double stranded DNA. 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. 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.

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. 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.

It has been shown that Netropsin is active both against Gram-positive bacteria and Gram-negative bacteria.