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N9653

Netropsin dihydrochloride

Name: Netropsin dihydrochloride
Brand: SIGMA

From Streptomyces netropsis, ≥98% (HPLC), 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

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

200

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Properties

Product Name

Netropsin dihydrochloride, from Streptomyces netropsis, ≥98% (HPLC), powder

biological source

Streptomyces netropsis

Quality Level

200

assay

≥98% (HPLC)

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

Description

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.

Disclaimer

Protect from light.

Storage Class

11 - Combustible Solids

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

涉药品监管产品

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Certificates of Analysis (COA)

Lot/Batch Number

0000455911

0000465983

0000430623

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Complexity in the binding of minor groove agents: netropsin has two thermodynamically different DNA binding modes at a single site.

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

The minor-groove binding DNA-ligands netropsin, distamycin A and berenil cause polyploidisation via impairment of the G2 phase of the cell cycle.

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

Netropsin and bis-netropsin analogs as inhibitors of the catalytic activity of mammalian DNA topoisomerase II and topoisomerase cleavable complexes.

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

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Global Trade Item Number

SKU	GTIN
N9653-5MG	04061834118886