Bacterial nitroreductase enzymes that can efficiently catalyse the oxygen-independent reduction of prodrugs originally developed to target tumour hypoxia offer great potential for expanding the therapeutic range of these molecules to aerobic tumour regions, via the emerging cancer strategy of gene-directed enzyme prodrug therapy (GDEPT). Two promising hypoxia prodrugs for GDEPT are the dinitrobenzamide mustard PR-104A, and the nitrochloromethylbenzindoline prodrug nitro-CBI-DEI. We describe here use of a nitro-quenched fluorogenic probe to identify MsuE from Pseudomonas aeruginosa as a novel nitroreductase candidate for GDEPT. In SOS and bacteria-delivered enzyme prodrug cytotoxicity assays MsuE was less effective at activating CB1954 (a first-generation GDEPT prodrug) than the

1ICR: The structure of Escherichia coli nitroreductase complexed with nicotinic acid: three crystal forms at 1.7 A, 1.8 A and 2.4 A resolution.

The overall goal of our research is to investigate mechanisms of chemical toxicity. We are particularly interested in genetic effects. These include examining how chemicals induce mutations, and also determining how different compounds alter gene regulation. Our approaches are primarily molecular, and we apply new technologies to our experimental objectives whenever possible.. Bacterial Nitroreductases. Several nitrosubstituted compounds (NSCs) are potent antimicrobial agents and others are important environmental pollutants. Nitroreductases (NRs) are enzymes that bioactivate NSCs. Our ongoing studies in this area involve cloning and characterizing microbial NRs and examining their mode of regulation. We have shown that NRs may be useful as activating enzymes for Enzyme Prodrug Therapy, a novel cancer chemotherapeutic strategy based on activation of nontoxic prodrugs to cytotoxic products in a tumor-specific manner. MUTAGENESIS AND DNA REPAIR. We have a long-standing interest in determining how ...

The data indicate that FA1090(M1) possessed a small insertion of 7 nucleotides about midway through the coding sequence, producing a frame shift mutation in nfsB. This genetic data supported the hypothesis that the nitrofurantoin resistant phenotype is due to the loss of nitroreductase activity. Conclusive evidence that this gene was responsible for nitrofurantoin resistance was obtained by deleting the coding. sequence for this gene from FA1090 and then demonstrating that FA1090NfsB-BsmIS lacked nitroreductase https://www.selleckchem.com/products/bix-01294.html activity (data not shown). Identification of the genetic basis of spontaneous nitrofurantoin resistant mutants We isolated numerous independent spontaneous nitrofurantoin resistant mutants and determined the DNA sequence of the buy GDC-0449 nfsB gene in these strains. Most of these mutants (90%) possessed the insertion of an adenine in a run of 5 adenines near the beginning of the gene, suggesting a bias for base insertion during. DNA ...

As the appreciation for anaerobic bacteriology has grown, it has become apparent that the isolation of Bacteroides species from clinical isolates is a significant finding. Studies by Redondo et al. (15) and Nguyen et al. (14) have linked Bacteroides bacteremia to higher mortality rates, which can be further affected by the use of inactive antimicrobials in the treatment regimen.. The class of 5-nitroimidazole drugs (metronidazole, tinidizole, and ornidizole) exerts antimicrobial actions via inhibition of DNA synthesis (19). This action requires intracellular reduction of the nitro group of these prodrugs to produce reactive radical species. Although the 5-nitroimidazole drugs were introduced into clinical practice in 1960, resistance of B. fragilis to these drugs was not described until 1978 (10) and remains rare (1, 20-22). The first metronidazole-resistant Bacteroides isolates were found to have altered end products of glucose metabolism that conferred distinctive biochemical and growth ...

Inducible and sell-specific gene KO with shRNA. For further reading:. http://cre.jax.org/introduction.html. http://link.springer.com/protocol/10.1385/1-59259-065-9:477#page-1. Update. I re-read OP question and, as commented to it, feel some confusion. So I would like to mention as well way to express mutated gene in specific tissue that, when expressed constitutively (all the time, everywhere), is lethal. Imagine some very strong oncogene. Or something like cell-toxic protein, e.g. chemically-activatable nitroreductase or light-activatable Killer-red. Or it might be mutated version of your favourite synaptic protein that, when expressed in all neurons, causes severe lethal phenotype.. What you do, is create transgenic animal with transgene-GFP fusion (nitroreductase, KillerRed, etc) that has floxed stop-codons in front, and cross that animal with transgenic with tissue-specific CreER (for example). What you get is animal that, when injected with tamoxifen, start to express mutated gene/toxic ...

CP001022.PE191 Location/Qualifiers FT CDS_pept complement(209651..210208) FT /codon_start=1 FT /transl_table=11 FT /locus_tag=Exig_0193 FT /product=nitroreductase FT /note=PFAM: nitroreductase; KEGG: bsu:BSU08480 FT hypothetical protein FT /db_xref=EnsemblGenomes-Gn:Exig_0193 FT /db_xref=EnsemblGenomes-Tr:ACB59679 FT /db_xref=GOA:B1YHE7 FT /db_xref=InterPro:IPR000415 FT /db_xref=InterPro:IPR026021 FT /db_xref=InterPro:IPR029479 FT /db_xref=UniProtKB/TrEMBL:B1YHE7 FT /protein_id=ACB59679.1 FT /translation=MNTRQLILERRSVRAYTDQPVPNEMIEEILEAAIYAPTHKLREPW FT RFVLVNEESQERYVDQLMTLLAKRGQLDQKTDEQRQMMRQKFADVPVYLTVLYEVKGTE FT DQQMEDLLATAAMIQNVQLLATELGLGCCWKSGKHWFTEEYAEMIGASENERVAGIIQF FT GWPALIPPLKKRTAARDKLTHF atgaacaccc gacaactgat tttagaacga cgatccgtcc gtgcttacac cgatcagccg 60 gttccaaatg aaatgattga agaaattctc gaagccgcca tctatgctcc gactcataaa 120 ttgcgtgaac cttggcgatt tgtcctcgtt aacgaagaaa gccaagagcg gtatgtcgac 180 caattgatga cgctgcttgc caagcgggga cagctggatc aaaaaacaga cgaacaacgc 240 ...

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The PDB archive contains information about experimentally-determined structures of proteins, nucleic acids, and complex assemblies. As a member of the wwPDB, the RCSB PDB curates and annotates PDB data according to agreed upon standards. The RCSB PDB also provides a variety of tools and resources. Users can perform simple and advanced searches based on annotations relating to sequence, structure and function. These molecules are visualized, downloaded, and analyzed by users who range from students to specialized scientists.

2,2-Diallylazetidine; CAS Number: 889939-55-3; Linear Formula: C9H15N; find Combi-Blocks, Inc.-COMH042386FF MSDS, related peer-reviewed papers, technical documents, similar products & more at Sigma-Aldrich

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Gene directed enzyme prodrug therapy (GDEPT) of cancer aims to improve the selectivity of chemotherapy by gene transfer, thus enabling target cells to convert nontoxic prodrugs to cytotoxic drugs. A zone of cell kill around gene-modified cells due to transfer of toxic metabolites, known as the bystander effect, leads to tumour regression. Here we discuss the implications of either striving for a strong bystander effect to overcome poor gene transfer, or avoiding the bystander effect to reduce potential systemic effects, with the aid of three successful GDEPT systems. This review concentrates on bystander effects and drug development with regard to these enzyme prodrug combinations, namely herpes simplex virus thymidine kinase (HSV-TK) with ganciclovir (GCV), cytosine deaminase (CD) from bacteria or yeast with 5-fluorocytodine (5-FC), and bacterial nitroreductase (NfsB) with 5-(azaridin-1-yl)-2,4-dinitrobenzamide (CB1954), and their respective derivatives.

Three 2,4,6-trinitrotoluene (TNT) nitroreductases from Klebsiella sp. C1 have different reduction capabilities that can degrade TNT by simultaneous utilization of two initial reduction pathways. Of these, nitroreductase II was purified to homogeneity by sequential chromatographies. Nitroreductase II...

1ylu: Structural and mechanistic studies of Escherichia coli nitroreductase with the antibiotic nitrofurazone. Reversed binding orientations in different redox states of the enzyme.

Virus-directed enzyme prodrug therapy (VDEPT) utilising the bacterial enzyme nitroreductase delivered by a replication-defective adenovirus vector to activate the prodrug CB1954 is a promising strategy currently undergoing clinical trials in patients with a range of cancers. An understanding of the

The present brief account relates our discovery of new reactions revolving around the chemistry of the NO2 group. It covers the condensation of MeNO2 with hindered ketones, and the synthesis of pyrroles, triazoles, and enamides. It also describes new transformations of allylic nitro compounds, such as their conversion to allylic sulfones and unsaturated lactones, their sigmatropic rearrangement into allylic nitrites and thence into allylic alcohols, as well as their use in a short synthesis of nitroestrone derivatives. This is followed by an unusual reduction method furnishing unsubstituted amines (RRC?NH) under conditions where these hydrolytically labile species can be captured inter- or intramolecularly. Finally, a mechanistic study of a strange alkyne-forming reaction, first reported by Abidi and later shown by Corey and co-workers to proceed through allylic nitro intermediates, ultimately led to a practical and powerful synthesis of alkynes starting from beta-keto esters.

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1idt: Studies on the nitroreductase prodrug-activating system. Crystal structures of complexes with the inhibitor dicoumarol and dinitrobenzamide prodrugs and of the enzyme active form.

Principal Investigator：IZUMI Yusuke, Project Period (FY)：1991 - 1992, Research Category：Grant-in-Aid for Developmental Scientific Research (B), Research Field：有機工業化学

PA 824: nitroimidazopyran derived from 5-nitroimidazoles; a prodrug that requires activation by a bacterial F420-depedent glucose-6-phosphate dehydrogenase (Fgd) and nitroreductase to activate components that then inhibit bacterial mycolic acid and protein synthesis; structure in first source

Nitrofurans are a class of drugs that have the ability to kill micro-organisms. The group consists of four drugs. Since 1989, nitrofurazone has been

DESCRIPTION (provided by applicant): In response to NIH RFA: RM-12-014, it is proposed to engineer exosomes, the bodys natural antigen delivery system, in order to enhance their natural capacity to activate reductive prodrugs and attach to their surface ligands that specifically target HER2-positive breast cancer, many cases of which are resistant to the current therapies (e.g., trastuzumab) . This will be done for an enzyme-activated prodrug therapy newly discovered by the P.I. (A.C. Matin, Ph.D.). The prodrug is 6-chloro-9-nitro-5-oxo-5H-benzo-(a)-phenoxazine (CNOB), and the humanized enzyme improved by the PI is hChrR43. A highly helpful feature of this regimen is that the activated cytotoxic product of CNOB, 9-amino-6-chloro-5H-benzo[a]phenoxazine-5-one (MCHB), is strongly fluorescent and can be visualized in living mice. This property makes an observational approach possible, and will minimize the need for mouse sacrifice and the use of more involved tests, e.g., LC/MS/MS, ...

Electrically conductive complexes of polypyrroles with nitroaromatic anions are prepared by polymerizing pyrrole, an N-alkylpyrrole and/or an N-arylpyrrole by anodic oxidation in a polar solvent, in the presence of a salt of an acidic nitroaromatic compound.

Exposure to nitroaromatic compounds has been reported to result in unextractable residues, or residues not readily extracted by traditional techniques. However, limited information is available about the formation rate ...

Nitryl chloride is a nitro compound in which the nitrogen of the nitro group is bonded to a chlorine.It is used as a nitrating and chlorinating agent in organic synthesis. It has a role as an oxidising agent, an apoptosis inducer and a reagent.. Nitryl chloride is a volatile inorganic compound with formula ClNO2. At standard conditions it is a gas. Nitryl chloride can be formed in the reaction of

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Oh, Danny…. Pro-drug people may be stoo-pid, but at least we are consistent. Right? Lets call a spade a spade. I vaguely recall an earlier post somewhere that talks about a stint you had at a grocery store and how appalled you were that we werent allowed to be adults in this country anymore…correct? How dare they ask an 85 year old man for I.D. on cigarettes? How dare they? Is he not an adult? And, now trying to pass a law about people smoking in cars with children…the nerve. Arent people free agents? Must we mandate everything? Now, a man cant even smoke a cigarette in his own car with his infant. The outrage! I remember it well, how you lambasted society for infringing on somebodys right. I believe you ended with, Whats next? You cant smoke in your own house? Um, yes, pardon me for the huge smirk on my face. It is so funny how those pesky Conservatives are all about less government, fewer laws…well, until they want them. You know, it is completely outrageous to try and tell ...

Fifty cases of nitrofurantoin-associated hepatic injury and two cases of nifurtoinol (hydroxymethylnitrofurantoin)-associated hepatic injury reported to the Netherlands Centre for Monitoring of Adverse Reactions to Drugs were analyzed in detail. In 38 cases, a causal relationship was considered like …

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Methyl 3-amino-3-[3-(trifluoromethyl)phenyl]propanoate; CAS Number: 1038323-37-3; Linear Formula: C11H12F3NO2; find Combi-Blocks, Inc.-COMH93D5D7BF MSDS, related peer-reviewed papers, technical documents, similar products & more at Sigma-Aldrich

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The nitroheterocycle nifurtimox, as part of a nifurtimox-eflornithine combination therapy, represents one of a limited number of treatments targeting Trypanosoma brucei, the causative agent of human African trypanosomiasis. The mode of action of this prodrug involves an initial activation reaction catalysed by a type I nitroreductase (NTR), an enzyme found predominantly in prokaryotes, leading to the formation of a cytotoxic unsaturated open chain nitrile metabolite. Here, we evaluate the trypanocidal activity of a library of other 5-nitrofurans against bloodstream form T. brucei as a preliminary step in the identification of additional nitroaromatic compounds that could potentially partner eflornithine. Biochemical screening against purified enzyme revealed that all 5-nitrofurans were effective substrates for TbNTR with the preferred compounds having apparent k(cat)/K(M) values approximately 50-fold greater than nifurtimox. For several compounds, in vitro reduction by this nitroreductase ...

Nitro compounds are organic compounds that contain one or more nitro functional groups (−NO2). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature, being almost invariably produced by nitration reactions starting with nitric acid. Aromatic nitro compounds are typically synthesized by nitration. Nitration is achieved using a mixture of nitric acid and sulfuric acid, which produce the nitronium ion (NO2+), which the electrophile: + H+ The nitration product produced on the largest scale, by far, is nitrobenzene. Many explosives are produced by nitration including trinitrophenol ...

Generation of nitro radical anions of some 5-nitrofurans, 2- and 5-nitroimidazoles by norepinephrine, dopamine, and serotonin. A possible mechanism for neurotox

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Metronidazole is taken up by anaerobes and then it is reduced to ferredoxin. This reduction will produce a toxic metabolite that kills anaerobes and protozoa ...

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