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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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T A Beerman et al.
Biochimica et biophysica acta, 1090(1), 52-60 (1991-08-27)
This study examined the ability of netropsin and related minor groove binders to interfere with the actions of DNA topoisomerases II and I. We evaluated a series of netropsin dimers linked with flexible aliphatic chains of different lengths. These agents
Irina Belozerova et al.
Journal of the American Chemical Society, 134(45), 18667-18676 (2012-10-11)
A variety of solution methods exist for analysis of interactions between small molecule ligands and nucleic acids; however, accomplishing this task economically at the scale of hundreds to thousands of sequences remains challenging. Surface assays offer a prospective solution through
M Poot et al.
Experimental cell research, 218(1), 326-330 (1995-05-01)
DNA topoisomerases are enzymes governing the multitude of conformational changes DNA undergoes during the cell cycle. Several compounds are likely to interfere with specific steps of the catalytic cycle of these enzymes. Camptothecin arrests the activity of DNA topoisomerase I
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
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