N9653

Netropsin dihydrochloride

Name: Netropsin dihydrochloride
Brand: SIGMA
Price: 352 USD
Availability: InStock

From Streptomyces netropsis, ≥98% (HPLC), powder

Synonym(s):

Congocidin, Sinanomycin

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N9653-5MG

$352.00

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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

Key Documents

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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

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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1 of 4

This Item	N2001	N7758	SML1823
Sigma-Aldrich N9653 Netropsin dihydrochloride	Sigma-Aldrich N2001 Neostigmine bromide	Sigma-Aldrich N7758 Naloxone hydrochloride dihydrate	Sigma-Aldrich SML1823 Vosaroxin hydrochloride
assay ≥98% (HPLC and TLC)	assay ≥98% (HPLC and titration)	assay ≥98% (TLC and titration)	assay ≥98% (HPLC)
form powder	form powder	form powder	form powder
Quality Level 200	Quality Level 100	Quality Level 200	Quality Level 100
storage temp. −20°C	storage temp. -	storage temp. 2-8°C	storage temp. −20°C
solubility H₂O: 1 mg/mL	solubility H₂O: 1 g/mL, ethanol: soluble	solubility ethanol: 3.3 mg/mL, H₂O: 50 mg/mL	solubility H₂O: 1 mg/mL, clear (warmed)
color faintly yellow	color white	color white to off-white	color white to beige

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

wgk_germany

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number

0000455911

0000465983

0000430623

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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

Melting thermodynamics of reversible DNA/ligand complexes at interfaces.

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

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

Distinct patterns of cell cycle disturbance elicited by compounds interfering with DNA topoisomerase I and II activity.

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

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