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(12) Patent Application Publication (10) Pub. No.: US 2008/0032382 A1 Schnoor Et Al US 20080032382A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0032382 A1 Schnoor et al. (43) Pub. Date: Feb. 7, 2008 (54) METHODS AND COMPOSITIONS FOR Related U.S. Application Data DEGRADATION OF NITROAROMATIC AND NITRAMINE POLLUTANTS (62) Division of application No. 10/873,659, filed on Jun. 22, 2004, now Pat. No. 7,214,509. (75) Inventors: Jerald L. Schnoor, Iowa City, IA (US); (60) Provisional application No. 60/483.736, filed on Jun. Beniot Van Aken, Iowa City, IA (US) 30, 2003. Publication Classification Correspondence Address: (51) Int. C. EDWARDS ANGELL PALMER & DODGE CI2N L/20 (2006.01) LLP (52) U.S. Cl. .......................................................... 435/252.3 P.O. BOX SS874 BOSTON, MA 02205 (US) (57) ABSTRACT The invention relates to novel Methylobacterium species (73) Assignee: University of Iowa Research Founda that are capable of degrading nitroaromatic and nitramine tion compounds. Compositions, kits and methods of using the Methylobacterium species for the degradation of nitroaro matic and nitramine pollutants are provided. More specifi (21) Appl. No.: 11/800.919 cally, compositions and methods for the degradation or bioremediation of nitroaromatic and nitramine explosives (22) Filed: May 8, 2007 and explosive residues are provided. -o-, RDXControl -a- HMX a -a - HMX Control Time (d) O. 6 O.4. O. 2 Patent Application Publication Feb. 7, 2008 Sheet 1 of 14 US 2008/0032382 A1 Figure 1 CH, ON NO No, ot, “C”N on." N . N-/NO. NO, f No, ON TNT RDX HMX Patent Application Publication Feb. 7, 2008 Sheet 2 of 14 US 2008/0032382 A1 Figure 2 Methylobacterium extorquens (D32224) Strain BIOOf Methylobacterium rhodesianum (D32228) Methylobacterium zatmanii (L20804) Methylobacterium rhodinum (D32229) Methylobacterium nodulans (AF220763) Methylobacterium organophilum (D32226) Methylobacterium mesophilicum (AJ400919) Methylobacterium radiotolerans (D32227) Rhodopseudomonaspalustris (D25312) Methylosinus sporium (M95665) Rhodoplanes roseus (D25313) Agrobacterium tumefaciens (D14500) Rhodobium marinum (D30790) Magnetospirillum magnetotacticum (M58171) Hirschia battica (M52909) Sphingomonas paucimobilis (D13725) Escherichlacoli (JO1859) Pseudomonas aeruginosa (XO6684) . - Methanococcus vannieli (M36507) O.OS Patent Application Publication Feb. 7, 2008 Sheet 3 of 14 US 2008/0032382 A1 Figure 3 -O- TNT Control -o- RDX -o-, RDX Control -A- HMX - A - HMX Control Time (d) -o- RDX O. 2 -- HMX -o- Control Patent Application Publication Feb. 7, 2008 Sheet 4 of 14 US 2008/0032382 A1 Figure 4 120 100 C. -o- RDX 8O -o- RDX Control 6 O -- CO2. 40 -o- CO2 Control Time (d) -o- HMX -o- HMX Control -- CO2 -o- CO2 Control Patent Application Publication Feb. 7, 2008 Sheet 5 of 14 US 2008/0032382 A1 Figure 5 Time = 4 d Unknown AONTs DANs O 5 10 15 20 25 Retention Time (min) Patent Application Publication Feb. 7, 2008 Sheet 6 of 14 US 2008/0032382 A1 1OOO 800 600 4OO 2OO O 400 2OO Unknown Time = 55 d 200 1OO O 2 4 6 8 10 12 Retention Time (min) FIGURE 5B Patent Application Publication Feb. 7, 2008 Sheet 7 of 14 US 2008/0032382 A1 Patent Application Publication Feb. 7, 2008 Sheet 8 of 14 US 2008/0032382 A1 Patent Application Publication Feb. 7, 2008 Sheet 10 of 14 US 2008/0032382 A1 W BJ001" (AY251818) Methylobacterium thiocyanatum DSM 11490 (U58018) Methylobacterium rhodesianum JCM 2810 (D32228) Methylobacterium zatmani JCM2819 (D32230) Methylobacterium extorquens ATCC 14718 (AF293375) Methylobacterium chloromethanicum VKMB-2223 (AF198624) Methylobacterium lusitanum VKMB-2239 (AYOO9403) Methylobacterium suomiense VKMB-2238 (AYOO9404) Methylobacterium dichloromethanicum VKM B-21 91 (AF227128) Methylobacterium rhodinum JCM2811 (D32229) Methylobacterium organophilum JCM2833 (D32226) Methyobacterium mesophilicum JCM 2829 (AJ40091 9) - Methylobacterium fujisawaense DSM 5686 (AJ250801 ) Methylobacterium radiotolerans JCM2831 (D32227) Methylobacterium nodulans ORS2060 (AF22O763) Rhodopseudomonas palustris ATCC 17001 (D2531 2) Agrobacterium tumefaciens NCPPB 2437 (D14500) Escherichia coli 562 (JO1859) Figure 9 Patent Application Publication Feb. 7, 2008 Sheet 11 of 14 US 2008/0032382 A1 Figure 10 Patent Application Publication Feb. 7, 2008 Sheet 12 of 14 US 2008/0032382 A1 igure 11 Patent Application Publication Feb. 7, 2008 Sheet 13 of 14 US 2008/0032382 A1 's- is 1 & al SS 33 s4.S. Figure 12 US 2008/0032382 A1 Feb. 7, 2008 METHODS AND COMPOSITIONS FOR aromatic amino derivatives, which are poorly further trans DEGRADATION OF NITROAROMATIC AND formed (29, 33). Except with white-rot fungi, that secrete NITRAMINE POLLUTANTS powerful ligninolytic peroxidases (8, 54), no significant mineralization has been detected in biological systems (29). RELATED APPLICATIONS In contrast to TNT, whose limiting degradation step is the aromatic ring fission, as soon as nitramines RDX and HMX 0001. This application is a divisional patent application undergo a change of the molecular structure, the ring col of U.S. patent application Ser. No. 10/873,659, filed Jun. 22, lapses to generate small aliphatic metabolites (17. 53). 2004, which claims the priority of U.S. provisional patent While other decomposition mechanisms have been reported application No. 60/483,736, filed Jun. 30, 2003, the entirety (i.e. concerted decomposition, bimolecular elimination, or of which is incorporated herein by reference. hydrolysis (17)), biotransformation of RDX and HMX fre quently involves an initial reduction of the nitro groups to BACKGROUND OF THE INVENTION form nitroso and hydroxylamino derivatives (31). The latter decompose to unstable aliphatic nitramines, eventually con 0002 Nitroaromatic and nitramine compounds comprise verted into NO and CO (17.18). Due to different confor a class of pollutants known to have both toxic and carcino mations, HMX (crown-type) is chemically more stable and genic properties. Nitroaromatic and nitramine pollutants are therefore less amenable to biodegradation than RDX (chair frequently generated in the production of explosives, such as type) (17). TNT (2,4,6-trinotrotoluene), RDX (Royal demolition explo sive; hexahydro-1,3,5-trinitro-1,3,5-triazine) and HMX 0007 Bacteria of the genus Methylobacterium are strictly (High melting point explosive; octahydro-1,3,5,7-tetranitro aerobic, facultative methylotrophic, Gram-negative, rod 1,3,5,7-tetrazocine) (see FIG. 1). In particular, due to their shaped bacteria that are able to grow on one-carbon com low solubility, large quantities of water used in the produc pounds, i.e. methanol or methylamine (13.30. 51). Members tion of explosives tend to become contaminated during their of the genus Methylobacterium, which belongs to the C-2 production, leading to wastewater disposal problems. subclass of Proteobacteria, are distributed in a wide diversity 0003) First synthesized in 1863, TNT was used in the dye of natural and human-made habitats, including soils, air, industry before becoming in the 20th century the main dust, fresh water, aquatic sediments, marine environments, conventional explosive used worldwide. However, because water Supplies, bathrooms, and masonry (19, 51). Some of a higher stability and detonation power, nitramines HMX species have been described as opportunistic human patho and RDX are at the present time the most widespread gens (51). In addition, methylotrophic bacteria colonize the conventional explosives. Manufacture of nitro-substituted roots and the leaves of terrestrial and aquatic plant species explosives, testing and firing ranges, and destruction of (21, 34, 51). These bacteria are often red to pink due to the ammunition stocks have generated toxic wastes leading to presence of carotenoids and referred as pink-pigmented large-scale contamination of Soils and groundwater (44). facultative methylotrophs (PPFMs). Methylobacterium bac Seven nitro-substituted explosives, including TNT and teria are highly resistant to dehydration, freezing, chlorina RDX, have been listed as priority pollutants by the U.S. tion, UV light, ionizing radiations, and elevated tempera Environmental Protection Agency (EPA) (25). RDX, for tures (51). merly used as a rat poison, is in addition considered as possible carcinogen by the EPA (2, 28). HMX has been SUMMARY OF THE INVENTION listed as an EPA contaminant of concern (48). A lifetime 0008. The invention provides novel strains of Methylo health advisory of 2 ug L' of TNT in drinking water and a bacterium species and methods for using them and other water-quality limit of 105 ug L' of RDX have been rec species of the genus Methylobacterium. These bacteria are ommended (7, 37). Physicochemical properties, biodegra shown herein to have the capacity to degrade nitroaromatic dation, and toxicity of nitro-substituted explosives have and nitramine compounds, including, for example the explo been extensively reviewed in the literature (12, 18, 38, 43. sives TNT, HMX and RDX and their derivatives. The 45, 53). capacity of the newly identified bacteria to degrade Such 0004) The toxicity of TNT has been reported since the nitroaromatic and nitramine compounds provides new meth First World War among English ammunition workers. From ods for the decontamination of environmental materials laboratory studies TNT, RDX, and HMX have been found to containing such compounds. Degradation of nitroaromatic be toxic for most classes of organisms, including bacteria and nitramine compounds is generally accomplished by (46, 57), algae (46, 57), plants (35), earthworms (36), contacting the bacteria with the compounds. The contacting aquatic
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