Netropsin Dihydrochloride
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| Category | Antibiotics |
| Catalog number | BBF-05804 |
| CAS | 18133-22-7 |
| Molecular Weight | 503.40 |
| Molecular Formula | C18H26N10O3.2HCl |
| Purity | ≥98% |
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Description
It is a basic cytotoxic polypeptide produced by the strain of Streptomyces netropsis. It is a DNA minor groove binding ligand.
Specification
| Related CAS | 1438-30-8 (free base) |
| Synonyms | Congocidin Dihydrochloride; Sinanomycin Dihydrochloride; Netropsin Dihydrochloride; Congocidine Dihydrochloride; N'-(2-amidinoethyl)-4-(2-guanidinoacetamido)-1,1'-dimethyl-N,4'-Bi[pyrrole-2-carboxamide] Dihydrochloride; 4-[[2-[(Aminoiminomethyl)amino]acetyl]amino]-N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-1-methyl-1H-pyrrole-2-carboxamide Dihydrochloride |
| Storage | Store at -20°C |
| IUPAC Name | N-[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]-4-[[2-(diaminomethylideneamino)acetyl]amino]-1-methylpyrrole-2-carboxamide;dihydrochloride |
| Canonical SMILES | CN1C=C(C=C1C(=O)NC2=CN(C(=C2)C(=O)NCCC(=N)N)C)NC(=O)CN=C(N)N.Cl.Cl |
| InChI | 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 |
Properties
| Appearance | White to Slight Yellow Powder |
| Melting Point | 241-247°C |
| Solubility | Soluble in Water |
Reference Reading
1. Efficacy of netropsin dihydrochloride against the viability, cytopathogenicity and hemolytic activity of Trichomonas vaginalis clinical isolates
Maha Marzouk Abou Gamra, Hanan Hussein Kamel, Hayam Mohamed Ezz Eldin, Fatima Mohamed Taha Zahran J Infect Chemother. 2019 Dec;25(12):955-964. doi: 10.1016/j.jiac.2019.05.015. Epub 2019 Jun 10.
Trichomonas vaginalis (T. vaginalis) is a common sexually transmitted infection, affecting the urogenital tract. Trichomoniasis is customarily treated with metronidazole (MTZ). MTZ is known to cause undesirable side effects and there is several reports on MTZ resistant T. vaginalis. Thus, the present study aimed to in-vitro evaluate the activity of DNA minor groove binder drug ''Netropsin dihydrochloride'' against metronidazole-sensitive T. vaginalis isolates (G and U isolates) and resistant T. vaginalis isolate (ATCC50138) (R isolate). Netropsin was tested at concentrations ranging from 3.5 to 200 μg/ml. It showed effectiveness against all isolates with MLC of 12.5 μg/ml for G and U isolates and of 25 μg/ml for R isolate. Cytotoxicity assay of isolates exposed to the respective MLC of netropsin for 42 h showed a highly significant reduction in the death percentage of MCDK cell line as compared to the effect elicited by drug free controls. The hemolytic activity was evaluated by hemolytic assay and by monitoring the interaction of T. vaginalis isolates with human erythrocytes by inverted microscopy and scanning electron microscopy. The hemolytic assay showed (0%) hemolysis of RBCs incubated with T. vaginalis isolates treated with the corresponding MLC of netropsin for 24 h. Scanning electron microscopy revealed cytoskeletal deformities of netropsin treated isolates. Taken together, these observations suggest that netropsin is a promising therapy for T. vaginalis infection affecting its viability, virulence, cytopathogenic and hemolytic activity with a mechanism of action that might overcome T. vaginalis resistance to metronidazole.
2. Repair in Escherichia coli alkB mutants of abasic sites and 3-methyladenine residues in DNA
S Dinglay, B Gold, B Sedgwick Mutat Res. 1998 Mar;407(2):109-16. doi: 10.1016/s0921-8777(97)00065-7.
Escherichia coli alkB mutants are sensitive to methyl methanesulfonate and dimethylsulphate, and are defective in the processing of methylated DNA. The function of the AlkB protein has not been determined. Here, we show that alkB mutants are not defective in repairing several different types of potentially toxic DNA lesions that are known to be generated by MMS, including apyrimidinic and apurinic sites, and secondary lesions that could arise at these sites (DNA-protein cross-links and DNA interstrand cross-links). Also, alkB mutants were not sensitive to MeOSO2-(CH2)2-Lex, a compound that alkylates the minor groove of DNA generating primarily 3-methyladenine.
3. Sulfated Ceria Catalyzed Synthesis of Imidazopyridines and Their Implementation as DNA Minor Groove Binders
Surender Mohan, Shobith Rangappa, Nirvanappa C Anilkumar, Julian E Fuchs, Andreas Bender, Basappa, Kanchugarakoppal S Rangappa, Rakesh Bhatnagar Chem Biodivers. 2019 May;16(5):e1800435. doi: 10.1002/cbdv.201800435. Epub 2019 Apr 10.
The small molecules that bind to DNA minor groove are considered as potential therapeutic agents to fight against many human diseases. They induce cell death by interfering with transcription, replication and progression of cell cycle. Herein, we report the synthesis of imidazopyridine-3-amines using sulfated ceria catalyst by employing Groebkee-Blackburne-Bienayme reaction. We evaluated the possible antiproliferative and antimycobacterial activity against A549 cells and Mycobacterium tuberculosis, respectively. Among the tested compounds, N-tert-butyl-2-(2-butyl-4-chloro-1H-imidazol-5-yl)-5,7-dimethylimidazo[1,2-a]pyridin-3-amine (4g) was identified as cytotoxic heterocycle and antimycobacterial agent. Molecular docking studies of the imidazopyridine derivatives revealed the consistent positioning in the minor groove with a tight shape fit between receptor and ligands. Therefore, we speculate that new imidazopyridines induce their pharmacological effect by targeting the minor groove of DNA.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
