Synonym
Netropsin HCl; Netropsin hydrochloride; Congocidine; Sinanomycin;
IUPAC/Chemical Name
N-(3-amino-3-iminopropyl)-4-(4-(2-guanidinoacetamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamide dihydrochloride
InChi Key
SDRHUASONSRLFR-UHFFFAOYSA-N
InChi Code
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
SMILES Code
CN1C(C(NC2=CN(C(C(NCCC(N)=N)=O)=C2)C)=O)=CC(NC(CNC(N)=N)=O)=C1.Cl.Cl
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Netropsin dihydrochloride is a small-molecule MGB (minor-groove binder), inhibits the catalytic activity of isolated topoisomerase and interferes with the stabilization of the cleavable complexes of topoisomerase II and I in nuclei.
In vitro activity:
Netropsin suppressed the increase of intracellular proteolytic activity when added to B. megaterium incubated in a sporulation medium. Different concentrations of netropsin affected various aspects of protein catabolism differently.
Reference: Folia Microbiol (Praha). 1993;38(1):10-4. https://pubmed.ncbi.nlm.nih.gov/8388845/
In vivo activity:
Netropsin improved survival from endotoxaemia in wild-type mice, yet not in NOS2-deficient mice, supporting an important role for NOS2 in the beneficial effects of MGB administration. Netropsin significantly attenuated NOS2 promoter activity in macrophage transient transfection studies and the AT-rich HMGA1 DNA-binding site was critical for this effect.
Reference: Biochem J. 2009 Feb 15;418(1):103-12. https://pubmed.ncbi.nlm.nih.gov/18937643/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
125.0 |
248.32 |
| Water |
20.0 |
39.73 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
503.39
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Kucerová H, Chaloupka J. Netropsin inhibits the increase of intracellular Ca(2+)-dependent serine proteinase activity in sporulating Bacillus megaterium. Folia Microbiol (Praha). 1993;38(1):10-4. doi: 10.1007/BF02814541. PMID: 8388845.
2. Ueno A, Baek K, Jeon C, Agarwal K. Netropsin specifically enhances RNA polymerase II termination at terminator sites in vitro. Proc Natl Acad Sci U S A. 1992 May 1;89(9):3676-80. doi: 10.1073/pnas.89.9.3676. PMID: 1315032; PMCID: PMC525553.
3. Grant MA, Baron RM, Macias AA, Layne MD, Perrella MA, Rigby AC. Netropsin improves survival from endotoxaemia by disrupting HMGA1 binding to the NOS2 promoter. Biochem J. 2009 Feb 15;418(1):103-12. doi: 10.1042/BJ20081427. PMID: 18937643; PMCID: PMC2821790.
In vitro protocol:
1. Kucerová H, Chaloupka J. Netropsin inhibits the increase of intracellular Ca(2+)-dependent serine proteinase activity in sporulating Bacillus megaterium. Folia Microbiol (Praha). 1993;38(1):10-4. doi: 10.1007/BF02814541. PMID: 8388845.
2. Ueno A, Baek K, Jeon C, Agarwal K. Netropsin specifically enhances RNA polymerase II termination at terminator sites in vitro. Proc Natl Acad Sci U S A. 1992 May 1;89(9):3676-80. doi: 10.1073/pnas.89.9.3676. PMID: 1315032; PMCID: PMC525553.
In vivo protocol:
1. Grant MA, Baron RM, Macias AA, Layne MD, Perrella MA, Rigby AC. Netropsin improves survival from endotoxaemia by disrupting HMGA1 binding to the NOS2 promoter. Biochem J. 2009 Feb 15;418(1):103-12. doi: 10.1042/BJ20081427. PMID: 18937643; PMCID: PMC2821790.
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