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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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Ben L Kelly et al.
PloS one, 6(6), e21412-e21412 (2011-07-07)
AT-rich DNA, and the proteins that bind it (AT-hook proteins), modulate chromosome structure and function in most eukaryotes. Unlike other trypanosomatids, the genome of Leishmania species is unusually GC-rich, and the regulation of Leishmania chromosome structure, replication, partitioning is not
N P Bazhulina et al.
Biofizika, 57(2), 232-242 (2012-05-19)
Data obtained show that antiviral activities of bis-linked netropsin derivatives are targeted by specific complexes formed by helicase UL9 of herpes simplex virus type 1 with viral DNA replication origins, represented by two OriS sites and one OriL site. According
Federico Riccardi Sirtori et al.
ChemMedChem, 7(6), 1112-1122 (2012-04-11)
Postreplicative mismatch repair (MMR) is a cellular system involved in the recognition and correction of DNA polymerase errors that escape detection in proofreading. Of the various mismatched bases, T:G pairing in DNA is one of the more common mutations leading
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
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