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N9653

Sigma-Aldrich

Netropsin dihydrochloride

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

Synonyme(s) :

Congocidin, Sinanomycin

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About This Item

Formule empirique (notation de Hill):
C18H26N10O3 · 2HCl
Numéro CAS:
18133-22-7
Poids moléculaire :
503.39
Code UNSPSC :
12352200
ID de substance PubChem :
24897909
Nomenclature NACRES :
NA.77

Source biologique

Streptomyces netropsis

Niveau de qualité

200

Pureté

≥98% (HPLC and TLC)

Forme

powder

Couleur

faintly yellow

Solubilité

H2O: 1 mg/mL

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria
viruses

Mode d’action

DNA synthesis | interferes

Température de stockage

−20°C

Chaîne SMILES 

[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

Clé InChI

SDRHUASONSRLFR-UHFFFAOYSA-N

Actions biochimiques/physiologiques

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.

Attention

Protect from light.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

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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
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.
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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