WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H525748
CAS#: 1438-30-8 (free base)
Description: Netropsin is a DNA minor groove binder originally isolated from S. netropsis. It binds to A/T rich regions of DNA (Ka = 4.9 x 105 M-1 for poly(dA)poly(dT) DNA). Netropsin inhibits topoisomerase II (IC90 = 200 µM in a cell-free assay) and teniposide-induced crosslinks in nuclei from 935.1 mouse fibrosarcoma cells (IC50 = 65 µM). It is active against several bacteria, including S. aureus, S. typhosa, K. pneumoniae, and A. aerogenes with MIC values of 5, 10, 10, and 5 µg/ml, respectively. Netropsin (75 µg/ml) inhibits viral plaque formation in Shope fibroma virus- or vaccinia virus-infected BS-C-1 host cells.5 It increases survival in a mouse model of endotoxemia induced by LPS when administered at a dose of 25 mg/kg.
Hodoodo Cat#: H525748
Name: Netropsin free base
CAS#: 1438-30-8 (free base)
Chemical Formula: C18H26N10O3
Exact Mass: 430.22
Molecular Weight: 430.473
Elemental Analysis: C, 50.22; H, 6.09; N, 32.54; O, 11.15
This product is not in stock, which may be available by custom synthesis.
For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge).
Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.
Related CAS #: 1438-30-8 (free base) 18133-22-7 (HCl),
Synonym: Antibiotic 1142; Antibiotic T-1384; Antibiotic T1384; Antibiotic T 1384; Sinanomycin; Congocidin; Congocidine; F 6; F6; F-9; IA-887; IA887; IA 887; K-117; K117; K 117; Netropsin
IUPAC/Chemical Name: N-(3-amino-3-iminopropyl)-4-(4-(2-guanidinoacetamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamide
InChi Key: IDBIFFKSXLYUOT-UHFFFAOYSA-N
InChi Code: InChI=1S/C18H26N10O3/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)
SMILES Code: O=C(C1=CC(NC(C2=CC(NC(CNC(N)=N)=O)=CN2C)=O)=CN1C)NCCC(N)=N
Appearance: Solid powder
Purity: >98% (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: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
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
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 430.47 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Chung JH, Bhat A, Kim CJ, Yong D, Ryu CM. Combination therapy with polymyxin B and netropsin against clinical isolates of multidrug-resistant Acinetobacter baumannii. Sci Rep. 2016 Jun 16;6:28168. doi: 10.1038/srep28168. PubMed PMID: 27306928; PubMed Central PMCID: PMC4910107.
2: Andronova VL, Grokhovsky SL, Surovaya AN, Gursky GV, Galegov GA. Effect of dimeric netropsin analogue 15Lys-bis-Nt and acyclovir on the reproduction of herpes simplex virus type 1. The search for variants of herpes virus with drug resistance to 15Lys-bis-Nt and acyclovir. Dokl Biochem Biophys. 2015;460:42-6. doi: 10.1134/S1607672915010123. Epub 2015 Mar 13. PubMed PMID: 25772989.
3: Szerszenowicz J, Drozdowska D. Semi-automatic synthesis, antiproliferative activity and DNA-binding properties of new netropsin and bis-netropsin analogues. Molecules. 2014 Jul 31;19(8):11300-15. doi: 10.3390/molecules190811300. PubMed PMID: 25090119.
4: Ramos JP, Le VH, Lewis EA. Role of water in netropsin binding to an A(2)T(2) hairpin DNA site: osmotic stress experiments. J Phys Chem B. 2013 Dec 19;117(50):15958-65. doi: 10.1021/jp408077m. Epub 2013 Dec 5. PubMed PMID: 24274393.
5: andronova VL, Grokhovskiĭ SL, Surovaia AN, Gurskiĭ GV, Deriabin PG, L'vov DK, Galegov GA. [Estimation of activity of bis-netropsin derivatives based on a model of an experimental cutaneous herpes simplex virus disease of guinea pigs]. Vopr Virusol. 2013 Jan-Feb;58(1):32-5. Russian. PubMed PMID: 23785759.
6: Ghosh S, Salsbury FR Jr, Horita DA, Gmeiner WH. Cooperative stabilization of Zn(2+):DNA complexes through netropsin binding in the minor groove of FdU-substituted DNA. J Biomol Struct Dyn. 2013;31(11):1301-10. doi: 10.1080/07391102.2012.732343. Epub 2012 Nov 16. PubMed PMID: 23153072; PubMed Central PMCID: PMC3825453.
7: Andronova VL, Grokhovskiĭ SL, Deriabin PG, Gurskiĭ GV, Galegov GA, L'vov DK. [Antiherpetic activity of netropsin derivatives as tested in experiments in laboratory animals]. Vopr Virusol. 2012 Jul-Aug;57(4):24-6. Russian. PubMed PMID: 23012980.
8: Bazhulina NP, Surovaia AN, Gurskiĭ IaG, Andronova VL, Arkhipova VS, Golovkin MV, Nikitin AM, Galegov GA, Gorokhovskiĭ SL, Gurskiĭ GV. [Inhibition of herpes simplex virus helicase UL9 by netropsin derivatives and antiviral activities of bis-netropsins]. Biofizika. 2012 Mar-Apr;57(2):232-42. Russian. PubMed PMID: 22594278.
9: Hansen N, Dolenc J, Knecht M, Riniker S, van Gunsteren WF. Assessment of enveloping distribution sampling to calculate relative free enthalpies of binding for eight netropsin-DNA duplex complexes in aqueous solution. J Comput Chem. 2012 Mar 5;33(6):640-51. doi: 10.1002/jcc.22879. Epub 2012 Jan 7. PubMed PMID: 22228455.
10: Lewis EA, Munde M, Wang S, Rettig M, Le V, Machha V, Wilson WD. Complexity in the binding of minor groove agents: netropsin has two thermodynamically different DNA binding modes at a single site. Nucleic Acids Res. 2011 Dec;39(22):9649-58. doi: 10.1093/nar/gkr699. Epub 2011 Sep 3. PubMed PMID: 21890907; PubMed Central PMCID: PMC3239193.
11: Andronova VL, Grokhovskiĭ SL, Galegov GA, Deriabin PG, Gurskiĭ GV, L'vov DK. [Antiviral properties of the derivatives of netropsin and distamycin against herpes simplex viruses type 1 and variolovaccine]. Vopr Virusol. 2010 Nov-Dec;55(6):24-7. Russian. PubMed PMID: 21381336.
12: Andac CA, Miandji AM, Hornemann U, Noyanalpan N. Use of the parmbsc0 force field and trajectory analysis to study the binding of netropsin to the DNA fragment (5'CCAATTGG)(2) in the presence of excess NaCl salt in aqueous solution. Int J Biol Macromol. 2011 May 1;48(4):531-9. doi: 10.1016/j.ijbiomac.2011.02.004. Epub 2011 Feb 16. PubMed PMID: 21335028.
13: Fang YY, Morris VR, Lingani GM, Long EC, Southerland WM. Genome-Targeted Drug Design: Understanding the Netropsin-DNA Interaction. Open Conf Proc J. 2010;1:157-163. PubMed PMID: 21297883; PubMed Central PMCID: PMC3032215.
14: Dolenc J, Gerster S, van Gunsteren WF. Molecular dynamics simulations shed light on the enthalpic and entropic driving forces that govern the sequence specific recognition between netropsin and DNA. J Phys Chem B. 2010 Sep 2;114(34):11164-72. doi: 10.1021/jp100483f. PubMed PMID: 20690690.
15: Zhang R, Wu X, Guziec LJ, Guziec FS, Chee GL, Yalowich JC, Hasinoff BB. Design, synthesis and biological evaluation of a novel series of anthrapyrazoles linked with netropsin-like oligopyrrole carboxamides as anticancer agents. Bioorg Med Chem. 2010 Jun 1;18(11):3974-84. doi: 10.1016/j.bmc.2010.04.028. Epub 2010 Apr 18. PubMed PMID: 20471276; PubMed Central PMCID: PMC2880227.
16: Ameerunisha Begum MS, Saha S, Nethaji M, Chakravarty AR. Iron(III) Schiff base complexes of arginine and lysine as netropsin mimics showing AT-selective DNA binding and photonuclease activity. J Inorg Biochem. 2010 Apr;104(4):477-84. doi: 10.1016/j.jinorgbio.2010.01.001. Epub 2010 Jan 11. PubMed PMID: 20106530.
17: Mishra K, Bhardwaj R, Chaudhury NK. Netropsin, a minor groove binding ligand: a potential radioprotective agent. Radiat Res. 2009 Dec;172(6):698-705. doi: 10.1667/RR1815.1. PubMed PMID: 19929416.
18: Premvardhan L, Maurizot JC. Netropsin binding in five duplex-dimer DNA constructs as a function of size and distance between binding sites: circular dichroism and absorption spectroscopy. Eur Biophys J. 2010 Apr;39(5):781-7. doi: 10.1007/s00249-009-0550-x. Epub 2009 Oct 28. PubMed PMID: 19859703.
19: Wolter FE, Molinari L, Socher ER, Schneider K, Nicholson G, Beil W, Seitz O, Süssmuth RD. Synthesis and evaluation of a netropsin-proximicin-hybrid library for DNA binding and cytotoxicity. Bioorg Med Chem Lett. 2009 Jul 15;19(14):3811-5. doi: 10.1016/j.bmcl.2009.04.042. Epub 2009 Apr 18. PubMed PMID: 19427785.
20: Patra AK, Bhowmick T, Roy S, Ramakumar S, Chakravarty AR. Copper(II) complexes of L-arginine as netropsin mimics showing DNA cleavage activity in red light. Inorg Chem. 2009 Apr 6;48(7):2932-43. doi: 10.1021/ic8017425. PubMed PMID: 19254037.
