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N9653

Sigma-Aldrich

Netropsin dihydrochloride

from Streptomyces netropsis, ≥98% (HPLC and TLC), powder

Synonym(s):

Congocidin, Sinanomycin

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About This Item

Empirical Formula (Hill Notation):
C18H26N10O3 · 2HCl
CAS Number:
18133-22-7
Molecular Weight:
503.39
UNSPSC Code:
12352200
PubChem Substance ID:
24897909
NACRES:
NA.77

biological source

Streptomyces netropsis

Quality Level

200

Assay

≥98% (HPLC and TLC)

form

powder

color

faintly yellow

solubility

H2O: 1 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
viruses

Mode of action

DNA synthesis | interferes

storage temp.

−20°C

SMILES string

[H]Cl.[H]Cl.NC(CCNC(C1=CC(NC(C2=CC(NC(CNC(N)=N)=O)=CN2C)=O)=CN1C)=O)=N

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

InChI key

SDRHUASONSRLFR-UHFFFAOYSA-N

Biochem/physiol Actions

Netropsin is an unusual n-methylpyrrole-containing oligopeptide that binds to AT-rich sequences of dsDNA, especially in the minor groove. Thus, it protects such regions from DNase I and other endonucleases, and also inhibits topoisomerases. Netropsin disrupts the cell cycle, prolonging G and arresting in G.

Caution

Protect from light.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Michael Rettig et al.
Chembiochem : a European journal of chemical biology, 14(3), 323-331 (2013-01-29)
With a growing understanding of the microstructural variations of DNA, it has become apparent that subtle conformational features are essential for specific DNA molecular recognition and function. DNA containing an A-tract has a narrow minor groove and a globally bent
C Zimmer et al.
Nucleic acids research, 8(13), 2999-3010 (1980-07-11)
The specific DNA binding ligand netropsin selectively blocks dA-dT base pairs in clusters containing two or more consecutive thymine residues at the dNAase I cleavage sites of DNA. Using CD and UV absorption measurements it is shown, that at various
Katy A Muzikar et al.
Organic letters, 13(20), 5612-5615 (2011-10-01)
A furan amino acid, inspired by the recently discovered proximicin natural products, was incorporated into the scaffold of a DNA-binding hairpin polyamide. While unpaired oligomers of 2,4-disubstituted furan amino acids show poor DNA-binding activity, furan (Fn) carboxamides paired with N-methylpyrrole
Souvik Maiti et al.
Biophysical chemistry, 159(1), 162-171 (2011-07-15)
We use a variety of biophysical techniques to determine thermodynamic profiles, including hydration, for the unfolding of DNA stem-loop motifs (hairpin, a three-way junction and a pseudoknot) and their interaction with netropsin and random cationic copolymers. The unfolding thermodynamic data
Niels Hansen et al.
Journal of computational chemistry, 33(6), 640-651 (2012-01-10)
The performance of enveloping distribution sampling (EDS) simulations to estimate free enthalpy differences associated with seven alchemical transformations of A-T into G-C base pairs at the netropsin binding site in the minor groove of a 13-base pair DNA duplex in
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