Disease relevance of nitramide

• Metabolism of the aliphatic nitramine 4-nitro-2,4-diazabutanal by Methylobacterium sp. strain JS178 [1].
• The aliphatic nitramine 4-nitro-2,4-diazabutanal (NDAB; C2H5N3O3) is a ring cleavage metabolite that accumulates during the aerobic degradation of the energetic compound hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by various Rhodococcus spp [1].
• Chemotaxis-mediated biodegradation of cyclic nitramine explosives RDX, HMX, and CL-20 by Clostridium sp. EDB2 [2].
• The polycyclic nitramine CL-20 (2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane) is a powerful explosive that may replace RDX and HMX, but its toxicity is not known [3].
• This study indicates that nitramine reduction in enteric bacteria is carried out by the type I, or oxygen-insensitive nitroreductase, rather than a type II enzyme [4].

High impact information on nitramide

• Furthermore, tetryl and 4,6-dinitrobenzofuroxan efficiently inactivated TrxR, likely by alkylation of the selenolthiol motif as in the inhibition of TrxR by 1-chloro-2,4-dinitrobenzene/dinitrochlorobenzene (DNCB) or juglone [5].
• DNCB, juglone, and tetryl were highly cytotoxic and induced caspase-3/7 activation in HeLa cells [5].
• At T > -40 degrees C, the N7-nitramine intermediate undergoes a nitramine rearrangement, which generates a C2-nitro species that immediately eliminates TFA to give 2-nitro-6-chloro-9-Boc purine 10 [6].
• Using the rate data and EPR spin concentration data, the ratio of free .NO2 produced per parent nitramine molecule is estimated as 1:1 for RDX and 4:1 for HNIW [7].
• The ability to separate nitroaromatic and nitramine explosives in seawater sample matrices is demonstrated using both MEKC and CEC [8].

Chemical compound and disease context of nitramide

• Allergic contact dermatitis from tetryl and trinitrotoluene [9].

Biological context of nitramide

• ESI produced a five-fold increase in detector response over atmospheric pressure chemical ionization (APCI) for the nitramine compounds, while the more energetic APCI produced more than twenty times the ESI response for nitroaromatics [10].
• Alkaline hydrolysis of the cyclic nitramine explosives RDX, HMX, and CL-20: new insights into degradation pathways obtained by the observation of novel intermediates [11].
• TNB and tetryl were positive in TA98 (32.5, 5.2revertants/nmole) and TA100 (7.4, 9.5revertants/nmole) without metabolic activation and were more potent than TNT (TA98, 0.3revertants/nmole; TA100, 2.4revertants/nmole) [12].
• In vitro enzyme and functional gene expression studies have implicated a limited number of enzymes/genes involved in cyclic nitramine catabolism [13].
• A variety of process modifications (i.e. addition of fertilizer, microbial biomass, purging with nitrogen, etc.) that were performed during the course of the experiment did not increase the tetryl biodegradation rate beyond the rates of degradation without modifications [14].

Associations of nitramide with other chemical compounds

• The biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) in liquid cultures with municipal anaerobic sludge showed that at least two degradation routes were involved in the disappearance of the cyclic nitramine [15].
• Rat liver DT-diaphorase (EC 1.6.99.2) catalyzed reductive N-denitration of tetryl (2,4,6-tri-nitrophenyl-N-methylnitramine) and 2,4-dinitrophenyl-N-methylnitramine, oxidizing the excess of NADPH [16].
• Results show that oxidation efficiencies in Fenton system are in the following sequence: DNT > PA > AP > TNT > Tetryl > RDX > HMX [17].
• Hexanitrohexaazaisowurtzitane (CL-20), a new polycyclic polynitramine, has the same functional nitramine groups (N-NO2) as the widely used energetic chemicals hexahydro-1,3,5-trinitro-1,3,5-triazacyclohexane (royal demolition explosive [RDX]) and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (high-melting explosive [HMX]) [18].
• Biodegradation mechanisms for cyclic nitramines include (a) formation of a nitramine free radical and loss of nitro functional groups, (b) reduction of nitro functional groups, (c) direct enzymatic cleavage, (d) alpha-hydroxylation, or (e) hydride ion transfer [13].

Gene context of nitramide

• DT-diaphorase catalyzes N-denitration and redox cycling of tetryl [16].
• Decomposition of the polycyclic nitramine explosive, CL-20, by Fe(0) [19].
• Predictably, a successful enzymatic change on one of the N-NO2 or C-H bonds of the cyclic nitramine would lead to a ring cleavage because the inner C-N bonds in RDX become very weak (<2 kcal/mol) [20].

Analytical, diagnostic and therapeutic context of nitramide

• Analysis of nitramine and nitroaromatic explosives in pink water by capillary electrophoresis [21].
• Cyclodextrin-assisted capillary electrophoresis for determination of the cyclic nitramine explosives RDX, HMX and CL-20 comparison with high-performance liquid chromatography [22].
• The military explosive N-methyl-N,2,4,6-tetranitroaniline (tetryl) is a direct acting mutagen in three microbial mutagenicity test systems at concentrations as low as 5 microgram/ml [23].
• The nitramine-containing solution underwent further cleanup with 6N HClO4-Celite and acid alumina-6% H2O microcolumns for subsequent analysis by gas chromatography interfaced with thermal energy analyzer and 63Ni electron capture detectors [24].

References