Skip to Content
Merck
All Photos(1)

Documents

N9653

Sigma-Aldrich

Netropsin dihydrochloride

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

Synonym(s):

Congocidin, Sinanomycin

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
M Poot et al.
Cell structure and function, 15(3), 151-157 (1990-06-01)
Distamycin A, netropsin and berenil are known to cause undercondensation of heterochromatic regions of metaphase chromosomes. These ligands interfere with DNA curvature by binding to the minor groove of the DNA. Whereas the effects of these ligands upon chromatin structure
Edwin A Lewis et al.
Nucleic acids research, 39(22), 9649-9658 (2011-09-06)
Structural results with minor groove binding agents, such as netropsin, have provided detailed, atomic level views of DNA molecular recognition. Solution studies, however, indicate that there is complexity in the binding of minor groove agents to a single site. Netropsin
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service