Furamidine dihydrochloride - CAS 55368-40-6
Category: Inhibitor
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Molecular Formula:
Molecular Weight:
Furamidine dihydrochloride is a protein arginine methyltransferase 1 (PRMT1) inhibitor (IC50 = 9.4 μM) in the class of antimicrobial and antiparasitic agents. It was shown to inhibit cell proliferation in leukemia cell lines.
Brife Description:
PRMT1 inhibitor
≥98% by HPLC
Related CAS:
73819-26-8 (free base)
4,4'-(2,5-Furandiyl)bis-benzenecarboximidamide dihydrochloride
Canonical SMILES:
1.Characterization of a novel DNA minor-groove complex.
Nguyen B;Hamelberg D;Bailly C;Colson P;Stanek J;Brun R;Neidle S;Wilson WD Biophys J. 2004 Feb;86(2):1028-41.
Many dicationic amidine compounds bind in the DNA minor groove and have excellent biological activity against a range of infectious diseases. Para-substituted aromatic diamidines such as furamidine, which is currently being tested against trypanosomiasis in humans, and berenil, which is used in animals, are typical examples of this class. Recently, a meta-substituted diamidine, CGP 40215A, has been found to have excellent antitrypanosomal activity. The compound has a linear, conjugated linking group that can be protonated under physiological conditions when the compound interacts with DNA. Structural and molecular dynamics analysis of the DNA complex indicated an unusual AT-specific complex that involved water-mediated H-bonds between one amidine of the compound and DNA bases at the floor of the minor groove. To investigate this unique system in more detail DNase I footprinting, surface plasmon resonance biosensor techniques, linear dichroism, circular dichroism, ultraviolet-visible spectroscopy, and additional molecular dynamics simulations have been conducted. Spectrophotometric titrations of CGP 40215A binding to poly(dAT)(2) have characteristics of DNA-binding-induced spectral changes as well as effects due to binding-induced protonation of the compound linker.
2.Unusual dehydroxylation of antimicrobial amidoxime prodrugs by cytochrome b5 and NADH cytochrome b5 reductase.
Saulter JY;Kurian JR;Trepanier LA;Tidwell RR;Bridges AS;Boykin DW;Stephens CE;Anbazhagan M;Hall JE Drug Metab Dispos. 2005 Dec;33(12):1886-93. Epub 2005 Aug 30.
Furamidine is an effective antimicrobial agent; however, oral potency of furamidine is poor. A prodrug of furamidine, 2,5-bis(4-amidinophenyl)furan-bis-O-methylamidoxime (DB289), has greatly improved oral potency. DB289 is transformed to furamidine via O-demethylation, and N-dehydroxylation reactions with four intermediate metabolites formed. The O-demethylation reactions have been shown to be catalyzed by cytochrome P450. The enzymes catalyzing the reductive N-dehydroxylation reactions have not been determined. The objective of this study was to identify the enzymes that catalyze N-dehydroxylation of metabolites M1, a monoamidoxime, and M2, a diamidoxime, formed during generation of furamidine. M1 and M2 metabolism was investigated using human liver microsomes and human soluble cytochrome b5 and NAD cytochrome b5 reductase, expressed in Escherichia coli. Kinetics of M1 and M2 reduction by human liver microsomes exhibited high affinity and moderate capacity. Metabolism was significantly inhibited by antibodies to cytochrome b5 and b5 reductase and by chemical inhibitors of b5 reductase. The amidoximes were efficiently metabolized by liver mitochondria, which contain cytochrome b5/b5 reductase, but not by liver cytosol, which contains minimal amounts of these proteins.
3.Efficacy of the diamidine DB75 and its prodrug DB289, against murine models of human African trypanosomiasis.
Thuita JK;Karanja SM;Wenzler T;Mdachi RE;Ngotho JM;Kagira JM;Tidwell R;Brun R Acta Trop. 2008 Oct;108(1):6-10. doi: 10.1016/j.actatropica.2008.07.006. Epub 2008 Aug 5.
The choice of drugs for the treatment of sleeping sickness is extremely limited. To redress this situation, the recently synthesised diamidine, 2,5-bis(4-amidinophenyl)-furan (DB75, furamidine) and its methamidoxime prodrug, 2,5-bis(4-amidinophenyl)-furan-bis-O-methylamidoxime (DB289, pafuramidine) were, together with pentamidine, evaluated for efficacy in acute rodent models. The activity was compared in three common mouse models that mimic the first stage of human African trypanosomiasis. The mice were infected with the pleomorphic T .b. rhodesiense strains KETRI2537 and STIB900 or with the monomorphic T. b. brucei strain STIB795. Importantly, DB75 showed activity superior to that of pentamidine at comparable doses in all three mouse models. Complete cures were achieved with oral dosing of the prodrug DB289 in all three models without any overt toxicity. This shows that the prodrug strategy was successful in terms of reducing toxicity and increasing efficacy and oral bioavailability.
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CAS 55368-40-6 Furamidine dihydrochloride

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