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1 hexanoic acid; dppz = dipyrido[3,2-a:2',3'-c]phenazine).
2 e production of virulence factors (including phenazines).
3 ys previously unknown coordination modes for phenazine.
4 hes it from other well-studied P. aeruginosa phenazines.
5 r type N,N'-disubstituted-dihydrodibenzo[a,c]phenazines.
6 ungal diseases by producing chemicals called phenazines.
7 our distinct redox-active metabolites called phenazines.
8 he survival effect is specific to endogenous phenazines.
9 es colorful, redox-active antibiotics called phenazines.
10 fluorescent pseudomonads produce and secrete phenazines.
11 CAM-1 and IL-8 increases in response to both phenazines.
12 soil bacterium Agrobacterium tumefaciens to phenazines.
13 nthesis of highly functionalized benzo fused phenazines.
14 ido[3,2-alpha: 2',3'-c:3'',2''-h:2''',3'''-j]phenazine) (1), was studied using cyclic voltammetry wit
15 trapyrido[3,2-a:2',3'-c:3",2''-h:2''',3'''-j]phenazine), 1(4+), is readily taken up by live cells loc
17 aeruginosa, pyocyanin (Py) and its precursor phenazine-1- carboxylic acid (PCA), and two chemically s
19 tified and was shown to control synthesis of phenazine-1-carboxamide from PCA in P. aeruginosa PAO1.
21 Pseudomonas fluorescens 2-79, which produces phenazine-1-carboxylate, is preceded by two genes, phzR
22 omplex would prevent the release of 5-methyl-phenazine-1-carboxylate, the putative intermediate, and
23 es including the recently described 5-methyl-phenazine-1-carboxylic acid (5MPCA), which exhibits a no
24 P. chlororaphis produces mainly two PZs, phenazine-1-carboxylic acid (PCA) and 2-hydroxy-PCA (2-O
26 f purified PhzF, -A, -B, and -G confirm that phenazine-1-carboxylic acid (PCA) is readily produced fr
27 phenazine production reveals distribution of phenazine-1-carboxylic acid (PCA) throughout the colony,
29 monstrated that the precursor for pyocyanin, phenazine-1-carboxylic acid (PCA), increases oxidant for
30 of PQS, likely induces the production of the phenazine-1-carboxylic acid (PCA), which in turn acts vi
33 n of the endogenous phenazines pyocyanin and phenazine-1-carboxylic acid in both cytosolic and membra
35 s of proteins that catalyze the synthesis of phenazine-1-carboxylic acid, the precursor for several p
38 y from the dipyrido[3,2-a:2',3'-c]-benzo[3,4]phenazine-11,16-quinone (NqPhen) ligand starting materia
39 has been demonstrated for 4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-(dimethylamino)-1-(R)-me
40 xic agents, exemplified by 4-methoxy-benzo[a]phenazine-11-carboxylic acid (2-(dimethylamino)-1-(R)-me
42 In alfalfa, treating roots with 200 microm phenazine, 2,4-diacetylphloroglucinol, or zearalenone in
43 1 (a 1:1 mixture of 9-hydroxy- and 6-hydroxy-phenazine-2-carobxylic acids), designed to recognize 1-h
45 inoxaline) (3), dppz (dipyrido[3,2-a:2',3'-c]phenazine) (4), dppn (benzo[i]dipyrido[3,2-a:2',3'-c]phe
46 e) (4), dppn (benzo[i]dipyrido[3,2-a:2',3'-c]phenazine) (5), and dap (4,7-dihydrodibenzo[de,gh][1,10]
48 zi](3+) (bpy, 2,2'-bipyridine; phzi, benzo[a]phenazine-5,6-quinone diimine) has been designed as a st
49 f diazapentacenes (5,14-diethynyldibenzo[b,i]phenazine, 6,13-diethynylnaphtho[2,3-b]phenazine) and te
50 ernative, which may affect the rate at which phenazines abstract electrons from the electron transpor
51 udomonas aeruginosa PA14, antibiotics called phenazines act as oxidants to balance the intracellular
55 y isolate two organic crystalline compounds, phenazine and caffeine, from their suspension in 1,4-dio
59 insights into the physiological functions of phenazines and has implications for designing effective
60 We have synthesized a series of ethynylated phenazines and their bis-triazolyl cycloadducts to serve
61 ly, Pseudomonas aeruginosa unable to produce phenazines and thus elicit UPR(mt) activation were hyper
62 o[b,i]phenazine, 6,13-diethynylnaphtho[2,3-b]phenazine) and tetraazapentacenes (7,12-diethynylbenzo[g
63 two U-shaped electron-acceptors (dibenzo[a,j]phenazine) and two electron-donors (N,N'-diphenyl-p-phen
64 l than loss of SoxR at low concentrations of phenazines, and also increases dependence on the otherwi
65 ystem to positively regulate biosynthesis of phenazine antibiotics that contribute to its association
66 g compounds, including endogenously produced phenazine antibiotics, induce expression of the efflux p
68 w that CcoN4 contributes to the reduction of phenazines, antibiotics that support redox balancing for
71 s it is unknown which producers and specific phenazines are ecologically relevant, and whether phenaz
76 primary aromatic amines produce substituted phenazines as major products, N-phenyl-o-phenylenediamin
79 esis and electrochemical evaluation of a new phenazine-based 2D COF (DAPH-TFP COF), as well as its co
81 uantitative metagenomic approach to mine for phenazine biosynthesis and biodegradation genes, applyin
85 ducer-crop associations and demonstrate that phenazine biosynthesis is prevalent across habitats and
87 yotic member of a large and widely conserved phenazine biosynthesis protein PhzF-like protein family.
88 an remodeling, uptake of phosphate and iron, phenazine biosynthesis, and other processes were identif
90 A crystal structure of PhzF, a key enzyme in phenazine biosynthesis, solved by molecular replacement.
94 low, inactivation of the rpeA gene enhanced phenazine biosynthetic gene expression and increased phe
100 E2F2G2, are homologous to previously studied phenazine biosynthetic operons from Pseudomonas fluoresc
101 vided into those with defects in the primary phenazine biosynthetic pathway and those with more pleio
103 electrophoresis showed increased amounts of phenazine biosynthetic proteins in FRD1 biofilms and in
104 ]phenazine (pzph), or benzo[a]pyrazino[2,3-h]phenazine (bpph) and dCF(3)ppy is 2-(3,5-bis(trifluorome
105 potentials for the PCET reactions at the GCC phenazine bridges and organic acid sites are in agreemen
107 ss or limitation stimulate the production of phenazines, but little is known of the molecular details
109 etrapyrido[3,2-a:2',3'-c:3",2"-h:2''',3'''-j]phenazine) by column chromatography and the characteriza
112 xtracellular redox-active molecules, such as phenazines, can broaden the metabolic versatility of mic
115 acene (1,4,8,11-tetrachloroquinoxalino[2,3-b]phenazine) carrying its chlorine atoms in the peri-posit
117 ters and experimentally validate a divergent phenazine cluster with potential new chemical structure
121 These studies suggest that P. aeruginosa phenazines coordinately up-regulate chemokines (IL-8) an
123 ed on the excited-state planarization of the phenazine core within these metallacycles results in the
124 a the coordination-driven self-assembly of a phenazine-cored dipyridyl donor with a 90 degrees Pt(II)
128 upporting phenazine utilization in biofilms, phenazine-dependent survival on ciprofloxacin is diminis
129 uginosa produces pyocyanin, a blue-pigmented phenazine derivative, which is known to play a role in v
130 sium diisopropylamide afforded alkyl-shifted phenazine derivatives 5a/5b, rather than the expected 9-
133 lo-2,2-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]phenazine derivatives with good to excellent yields.
134 n the P. fluorescens species complex produce phenazine derivatives, such as phenazine-1-carboxylic ac
135 o monohydrodeaminate the 2,3-di(methylamino) phenazine derivatives, which allows for further structur
137 n coculture biofilms, Pseudomonas aeruginosa phenazine-derived metabolites differentially modulated A
138 ppz and the cation ethylene-bipyridyldiylium-phenazine dinitrate [[1][(PF(6))(2)]] have been obtained
145 ore, 1e(-) oxidation of the DMS species with phenazine ethosulfate yields a Mo(V) form without an -OH
146 y, the N,N'-disubstituted-dihydrodibenzo[a,c]phenazines exhibit multiple emissions, which can be wide
149 Phenazine-1-carboxylic acid, the initial phenazine formed, is converted to pyocyanin in two steps
152 An axial chiral tetrachlorinated bisbenzo[a]phenazine has been discovered that undergoes an alkane-i
153 (4-formylphenyl) diquinoxalino[2,3-a:2',3'-c]phenazine (HATN-6CHO) and the first electron-donating li
155 ity relationships of a series of halogenated phenazines (HP) inspired by 2-bromo-1-hydroxyphenazine 1
157 lar synthesis of a library of 20 halogenated phenazines (HP), utilizing the Wohl-Aue reaction, that t
160 Pseudomonas aeruginosa produces several phenazines including the recently described 5-methyl-phe
162 ion of N,N'-disubstituted-dihydrodibenzo[a,c]phenazines, intramolecular charge-transfer takes place,
163 rapyrido[3,2-a:2',3'-c:3'',2''-h:2''',3'''-j]phenazine) is luminescent when bound to DNA and in organ
164 etion of pyocyanin, the best-studied natural phenazine, is responsible for the bluish tint of sputum
165 boxylic acid, the precursor to the bioactive phenazines, is synthesized from chorismic acid by enzyme
166 romatic pdppz ([2,3-h]dipyrido[3,2-a:2',3'-c]phenazine) ligand and exhibits photoactivity through inc
167 lysts are topologically connected via robust phenazine linkage into a two-dimensional tetragonal fram
169 phenazine-1-carboxylic acid (PCA), a common phenazine made by all phenazine-producing pseudomonads,
170 is by oxidizing NADH, our work suggests that phenazines may substitute for NAD(+) in LpdG and other e
173 ous spatial imaging of multiple redox-active phenazine metabolites produced by Pseudomonas aeruginosa
174 terest is the observation that P. aeruginosa phenazine metabolites were converted by A. fumigatus int
175 tages of infection, Pa produces redox-active phenazine metabolites, including pyocyanin (PYO), 5-meth
177 redox dye tetranitroblue tetrazolium (TNBT), phenazine methosulfate (PMS), NAD(+), and 6-phosphogluco
178 wo chemically synthesized pyocyanin analogs, phenazine methosulfate (PMS+) and phenazine ethosulfate
179 oxide generation, either through addition of phenazine methosulfate or by deletion of sodA and sodB,
180 th the cell membrane and exhibited D-lactate:phenazine methosulfate reductase activity and oxidized D
181 ransfer from ISP reduced with ascorbate plus phenazine methosulfate to cytochrome b was studied in SM
182 amide adenine dinucleotide phosphate (NADP), phenazine methosulfate, and iodonitrotetrazolium violet,
187 dative stress, it was shown that juglone and phenazine methylsulfate are potentially toxic to the par
188 ed by tert-butyl-hydroperoxide, juglone, and phenazine methylsulfate with IC(50) in the nanomolar ran
191 in is mediated in P. aeruginosa by two novel phenazine-modifying genes, phzM and phzS, which encode p
199 novel gene located downstream from the core phenazine operon that encodes a 55-kDa aromatic monooxyg
200 to manipulate organisms to produce multiple phenazines or novel phenazines not previously described.
201 nanthroline), dppz (dipyrido[3,2- a:2',3'- c]phenazine, or dppn (benzo[ i]dipyrido[3,2- a,2',3'- c]ph
202 olysaccharide, phospholipases, exoproteases, phenazines, outer membrane vesicles, type III secreted e
203 prior studies have focused on extracellular phenazine oxidation by oxygen and iron, here we report a
204 anin is produced from chorismic acid via the phenazine pathway, nine proteins encoded by a gene clust
209 mutants exhibiting reduced production of the phenazine poison pyocyanin were isolated following trans
212 diversity, frequency and ecological roles of phenazines produced by fluorescent Pseudomonas spp.
215 s the stage for improving the performance of phenazine producers used as biological control agents fo
216 re well known for their toxicity against non-phenazine-producing organisms, which allows them to serv
217 c acid (PCA), a common phenazine made by all phenazine-producing pseudomonads, to help P. aeruginosa
220 the tremendous diversity of plant-beneficial phenazine-producing Pseudomonas spp., paving the way for
221 ely, the media type significantly influences phenazine product distribution, especially in polymicrob
223 Herein, we investigate differences in Pa phenazine production and dynamics in polymicrobial commu
225 e biosynthetic gene expression and increased phenazine production but did not increase quorum sensing
235 lysis of mutants with various capacities for phenazine production reveals distribution of phenazine-1
246 biofilm development have focused on the blue phenazine pyocyanin and the yellow phenazine-1-carboxyli
247 quantitative RT-PCR, we demonstrate that the phenazine pyocyanin elicits the upregulation of genes/op
249 hat catalyze the reduction of the endogenous phenazines pyocyanin and phenazine-1-carboxylic acid in
250 secretes copious amounts of the redox-active phenazine, pyocyanin (PCN), during cystic fibrosis lung
251 8-tetraazaphenanthrene (TAP), pyrazino[2,3-a]phenazine (pzph), or benzo[a]pyrazino[2,3-h]phenazine (b
253 s readily synthesized by condensation of the phenazine quinone with the corresponding diammine comple
254 ical shift correlated with the production of phenazine radicals and concomitant reactive oxygen speci
257 which is available from the atmosphere, and phenazines, redox-active antibiotics produced by the bac
259 or reductants and catalysts of intracellular phenazine reduction in Pseudomonas aeruginosa Enzymatic
260 , diphenyleneiodonium, effectively inhibited phenazine reduction in vitro, suggesting that most phena
261 te dehydrogenase complexes directly catalyze phenazine reduction with pyruvate or alpha-ketoglutarate
263 Although repression plays a critical role in phenazine regulation, the rpeA mutation could not bypass
266 ilms show a profound morphogenic response to phenazines resulting from electron acceptor-dependent in
269 rating a novel binding mode in which the two phenazine rings bis-intercalate at the 5'-TpG site, with
270 estigated under aerobic conditions using two phenazine secondary metabolites excreted by P. aeruginos
271 tic pathogen Pseudomonas aeruginosa produces phenazines, small molecules that act as alternate electr
272 genes, phzM and phzS, which encode putative phenazine-specific methyltransferase and flavin-containi
274 s of chlorinated carbazole, phenoxazine, and phenazine suggests the formation of these species by ele
276 Previously, we reported that endogenous phenazines support the anaerobic survival of P. aerugino
277 he genetics, biochemistry, and regulation of phenazine synthesis, as well as the mode of action and f
278 ased infections, releases metabolites called phenazines that accept electrons to support cellular red
280 monads produce redox active compounds called phenazines that function in a variety of biological proc
281 ls encounter redox-active compounds, such as phenazines, that can generate oxidative stress, but the
283 henanthroline, dppz = dipyrido[3,2-a:2'.3'-c]phenazine), to study aggregation of alpha-synuclein (alp
286 aphenanthrene, dppz = dipyrido[3,2-a:2',3'-c]phenazine), undergoes a partial transition from an A/B h
287 les, the electron spins are localized on the phenazine unit, in which the sulfur atom of the fused th
288 specific respiratory complexes in supporting phenazine utilization in biofilms, phenazine-dependent s
289 in-like species, carbazole, phenoxazine, and phenazine via unimolecular rearrangements of diphenylami
290 hod for the construction of heteroaryl-fused phenazines was developed via PIFA-BF(3).Et(2)O-mediated
291 idine, dppn = benzo[i]dipyrido[3,2-a;2',3'-c]phenazine) was synthesized and characterized in an effor
292 le to co-crystallize LpdG with an endogenous phenazine, we report its X-ray crystal structure in the
295 quinoxaline, 6,13-diethynylquinoxalino[2,3-b]phenazine) were reduced to their radical anions and dian
296 redox-active metabolites, and in particular phenazines, which are produced by many bacteria found in
298 ces colorful redox-active metabolites called phenazines, which underpin biofilm development, virulenc
299 somer (2,3,9,10-tetrachloroquinoxalino[2,3-b]phenazine, with the chlorine atoms in the east and west
300 yridyl[3,2- a:2',3'- c:3",2"- h:2''',3'''- j]phenazine], with a mononuclear analogue with a modified