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1 ome b561, cytochrome b595, and cytochrome d (chlorin).
2 gy is applied to dyads of dihydroporphyrins (chlorins).
3 II particles of varying antenna size (8-250 chlorins).
4 he chlorin or by derivatization of an intact chlorin.
5 n amidinium-purpurin to produce an amidinium-chlorin.
6 re labile toward dehydrogenation to give the chlorin.
7 glet oxygen quantum yields found to the free chlorin.
8 ffording the 5,10-diaryl-15-halo-substituted chlorin.
9 mately 240 mV compared with that of the zinc chlorin.
10 exposed to air for 4-6 h, affording the zinc chlorin.
11 stable, enabling study of the conversion to chlorin.
12 etalated to give the corresponding free base chlorin.
13 between the isomeric 12- and 13-substituted chlorins.
14 l cations and radical anions of the examined chlorins.
15 developed for the synthesis of 7-substituted chlorins.
16 estern half provided access to 3-substituted chlorins.
17 rdless of synthetic or biological origin, to chlorins.
18 s are versatile precursors to porphyrins and chlorins.
19 round state as is found for low-spin Fe(III) chlorins.
20 nthetic tetrahydroporphyrins by reduction of chlorins.
21 s of readily prepared and oxidatively stable chlorins.
22 inker spans the 10-positions of the two zinc chlorins.
23 -fold, than with congeners that had no ortho chlorines.
24 eeds to PCDD/F congeners with less than four chlorines.
25 only strain to dehalogenate para-substituted chlorines.
26 lorines, but not doubly flanked or unflanked chlorines.
27 moving flanked para- and doubly flanked meta-chlorines.
29 cribed a new synthesis of C,D-ring symmetric chlorins 11, involving 2 + 2 condensation of bis-formyl-
32 tion of dihydrobenzoporphyrin 14 by reacting chlorin 3 with the phosphonium salt of p-methylbenzylbro
33 ing to this broadened in vitro activity, the chlorin 3-hydroxyethyl chlorophyllide a was newly identi
34 rption maximum (637-655 nm for the free base chlorins, 606-628 nm for the zinc chlorins) and intensit
35 tion of 8-phenanthrenevinylporphyrin 19 from chlorin 7 further confirmed our proposed mechanism for t
38 nitrogen isotope ratio, nitrogen content and chlorin abundance data from sediment cores with high acc
40 ta set of PCDD/F congeners with four or more chlorines along with all 209 polychlorinated biphenyl (P
41 porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2-oxachlorin
42 The morpholinochlorins, a class of stable chlorin analogues, were synthesized in two to three step
43 S, i.e., dipole-dipole) coupling in the ZnFb-chlorin and -oxochlorin dyads is enhanced relative to th
44 s of readily prepared and oxidatively stable chlorin and bacteriochlorin analogues with tunable optic
48 and various spectral characteristics of the chlorin and oxochlorin building blocks provide the found
50 ates and diminished efficiencies in the ZnFb chlorin and oxochlorin dyads versus the ZnFb porphyrin d
53 l window between that of analogous synthetic chlorins and 13(1)-oxophorbines (603-687 nm) and bacteri
58 free base chlorins, 606-628 nm for the zinc chlorins) and intensity of the chlorin Q(y)() band (epsi
59 ylene linker at the 13- or 3,13-positions of chlorin, and a second type where BODIPY is attached at t
60 sence of fused anhydride rings in porphyrin, chlorin, and bacterichlorin systems showed a significant
61 The ring-current strengths of the porphins, chlorins, and bacteriochlorins are 1.5-2.5 times stronge
62 The structures of the isolated porphyrins, chlorins, and bacteriochlorins, related to Bchl a, were
63 single regioisomers of diversely substituted chlorins, and in every case, the 2 + 2 condensation is a
65 the ethylene moiety from those in which the chlorines are located on the aromatic ring with the meth
66 we can distinguish the isomers in which the chlorines are located on the ethylene moiety from those
67 oxidatively dechlorinated, whereas the other chlorines are removed by a reductive process in which ch
70 the synthesis and characterization of BODIPY-chlorin arrays containing a chlorin subunit, with tunabl
73 posed of a common red-absorbing (645-646 nm) chlorin, as an energy donor, and a different near-IR emi
75 The arrays vary the tetrapyrrole (porphyrin, chlorin, bacteriochlorin), chromophore (boron-dipyrrin,
76 and optical properties of a series of novel chlorin-bacteriochlorin energy transfer dyads are descri
77 efficient energy transfer (>/=0.77) even for chlorin-bacteriochlorin pairs with large (up to 122 nm)
78 reatment strategy that combines PDT by a new chlorin-based nanoscale metal-organic framework (nMOF),
79 report here the rational design of the first chlorin-based nanoscale metal-organic framework (NMOF),
80 se amine complex, it was considered that the chlorin-based photosensitizers could be introduced into
86 hes have been developed for the synthesis of chlorins bearing formyl groups: (1) reaction of an aceta
87 te has been exploited to construct nine zinc chlorins bearing substituents at the 3- and 13-positions
88 o-flask process was applied to form six zinc chlorins bearing substituents such as pentafluorophenyl,
90 ase chlorins have been prepared wherein each chlorin bears a geminal dimethyl group in the reduced ri
92 d methodology for preparing meso-substituted chlorin building blocks and now present methodology for
94 ments introduced enable 100-mg quantities of chlorin building blocks to be prepared in a facile and r
97 preferentially dehalogenated singly flanked chlorines, but not doubly flanked or unflanked chlorines
98 ks in the synthesis of porphyrins, corroles, chlorins, calix[4]pyrroles, porphodimethenes, BODIPY dye
99 d to illuminate the scope to which synthetic chlorins can serve as surrogates for chlorophylls and be
101 f singlet oxygen produced by the sensitizers chlorin (Chl) and 5,10,15,20-tetrakis(N-methyl-4-pyridyl
103 des an access for novel carbon-carbon linked chlorin-chlorin dimers and chlorin-porphyrin dimers with
104 gher numbers of PEG groups, with the tri-PEG chlorin conjugate showing the best overall ovarian cance
107 he PEG groups in the mono-, di-, and tri-PEG chlorin conjugates increased the water solubility and se
108 chanism is suggested for the di- and tri-PEG chlorin conjugates; however, a more complicated process
109 oporphyrin, whereas a 13(1)-oxophorbine is a chlorin containing an annulated oxopentano ring spanning
110 pinacol-pinacolone conditions, vic-dihydroxy chlorins containing 4-methoxyphenyl or 3,5-dimethoxyphen
111 actose-conjugated purpurinimides (a class of chlorins containing a six-membered fused imide ring syst
112 the proposal that a native ligand of ferrous chlorin d is replaced by CN- to form the 5cHS d2+ cyano
114 ase perturbs a spin-state equilibrium in the chlorin d3+ to yield entirely the high-spin form of the
121 the natural abundance and (13)C-labeled zinc chlorin dyads and benchmark zinc chlorin monomers reveal
123 stigations reveal that the 17(3)-substituted chlorin e(6) conjugates are L-shaped, the 15(2) and 13(1
126 sign, MnO2 nanosheets adsorb photosensitizer chlorin e6 (Ce6), protect it from self-destruction upon
127 rombin aptamer and covalently linked it with Chlorin e6 (Ce6), which is a second generation photosens
128 mic therapy (PDT) was developed by designing chlorin e6 (Ce6)-containing macromolecules, which are se
130 1c1c7 cultures presensitized with N-aspartyl chlorin e6 (NPe6) caused lysosomal disruption and apopto
131 gate (P-A); (b) free and HPMA copolymer-meso-chlorin e6 monoethylene diamine disodium salt (Mce6) con
132 we demonstrate that such a photosensitiser, chlorin e6, can be repurposed for PCI by conjugating the
134 umulate an exogenous chlorophyll derivative, chlorin e6, that renders them as sensitive to red light
135 was developed to attach the photosensitizer chlorin(e6) (c(e6)) to the F(ab')2 fragment of the murin
136 es were prepared between the photosensitizer chlorin(e6) and various proteins (albumin, fibrinogen, a
137 fter i.v. injection of the polyanionic 17.1A chlorin(e6) conjugate or unconjugated photosensitizer.
139 onic charge had both a higher absolute tumor chlorin(e6) content and a greater tumor:normal liver rat
140 re conducted with the same MAb conjugated to chlorin(e6) followed by illumination to reduce expressio
141 etylated conjugate between poly-l-lysine and chlorin(e6) increased the relative phototoxicity in vitr
142 ith additional albumin added (2.5 protein to chlorin(e6) molar ratio) showed significantly higher wel
145 r detection or a photochemically active dye (chlorin(e6)) for therapy of early premalignancy in the h
146 body 17.1A conjugated to the photosensitizer chlorin(e6), and (b) to compare the tumor response after
147 ents using either a chlorin (mono-L-aspartyl chlorin-e6)- or purpurin (tin etio-purpurin)-based sensi
148 s with BODIPY attached at the 10-position of chlorin exhibit a bright fluorescence in a range of solv
149 ere BODIPY is attached at the 10-position of chlorin exhibit approximately 5-fold brighter fluorescen
150 tached at the 3- or at both 3,13-positons of chlorin exhibit significant reduction of fluorescence in
156 n of the position of the substituents (i.e., chlorines for PCBs and alkyl groups for alkylated-PAHs)
157 ogies provide expanded access to an array of chlorins for SAR studies that may advance the effectiven
158 , this study provides access to finely tuned chlorins for spectroscopic studies and diverse applicati
162 The formation of a bis-chromene-annulated chlorin from the bacteriochlorins is also described, inc
163 respectively, giving overall yields of zinc chlorin from the Eastern and Western halves of 12-45%.
164 s-chromene-annulated meso-(pentafluorophenyl)chlorins from meso-tetrakis(pentafluorophenyl)porphyrins
165 es for a rational, step-by-step synthesis of chlorins from readily available pyrrole precursors.
167 The dominant method for the synthesis of chlorins has entailed the derivatization of porphyrins.
172 ent, a geminal dimethyl group to lock in the chlorin hydrogenation level, and no flanking meso and be
173 nts, a geminal dimethyl group to lock in the chlorin hydrogenation level, and no flanking meso and be
177 the ring A of spirochlorin and the ring C of chlorin in our model dimer 9 mimic the ring A-ring A int
180 m this series indicate that ADAMs containing chlorines in the aromatic rings might bind to HIV-1 reve
183 With both ring-B reduced and ring-D reduced chlorins in hand, their photophysical and electrochemica
184 hotophysical properties of the water-soluble chlorins in phosphate-buffered saline solution (pH 7.4)
186 nerating chromene-annulated pyrrole-modified chlorins incorporating oxazolone and morpholine moieties
190 nochromene-annulated meso-(pentafluorophenyl)chlorin is susceptible to a regioselective OsO4-mediated
191 sitions are the most toxic, removal of these chlorines is advantageous, but previous studies have onl
197 hromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochl
198 is and fluorescence spectra) of the (metallo)chlorin-like chromophores that possess slightly red-shif
199 together, the synthesis of >1000 chlorins or chlorin-like compounds (containing >50 distinct pyrrolin
201 with a fixed chain length (n) and number of chlorines (m) are referred to as a "congener group" CnCl
202 yrroles that are derived from opening of the chlorin macrocycle by the Rieske-type oxygenase PHEOPHOR
203 ing in the conformational flexibility of the chlorin macrocycle direct the reactions toward the forma
204 duce a (13)C label at the 19-position of the chlorin macrocycle, which is a site of large electron/ho
207 (>/=0.80) energy transfer from BODIPY to the chlorin moiety in both toluene and DMF and exhibits inte
209 abeled zinc chlorin dyads and benchmark zinc chlorin monomers reveal that the time scale for hole/ele
215 sfer from a zinc chlorin to a free-base (Fb) chlorin occurs with a rate constant of (110 ps)(-1) and
216 der goal of synthesizing fully non-symmetric chlorins of general structure 15, which requires regiose
220 designated sites about the perimeter of the chlorin or 13(1)-oxophorbine macrocycle is essential for
222 duction of a third aryl substituent into the chlorin or oxochlorin causes an approximately 5-nm red s
224 zed for certain compounds bearing either two chlorines or two fluorines, and two methoxy groups gave
225 arrays containing PEG-substituted BODIPY and chlorins or bacteriochlorins were prepared and their opt
232 bon-carbon linked chlorin-chlorin dimers and chlorin-porphyrin dimers with fixed and flexible orienta
233 or bromination of a 5,10-diaryl-substituted chlorin proceeded with high regioselectivity, affording
234 on, and mass and NMR spectrometry as an iron chlorin product formed from the saturation of the double
237 for the zinc chlorins) and intensity of the chlorin Q(y)() band (epsilon up to 79 000 M(-)(1) cm(-)(
240 sential for photosynthesis, is composed of a chlorin ring and a geranylgeranyl diphosphate (GGPP)-der
241 tion of a transmembrane helix by a lipid and chlorin ring, (ii) lipid and beta-car connection of peri
243 zation of BODIPY-chlorin arrays containing a chlorin subunit, with tunable deep-red (641-685 nm) emis
244 alkyloxazolochlorins are compared to regular chlorins, such as 2,3-dihydroxychlorins and nonalkylated
245 mpared with those of isomeric 12-substituted chlorins, synthesized previously via a 7,9-dibromo-1-for
246 s the entire history since the beginnings of chlorin synthetic chemistry in the early 20th century th
248 ain to use chlorobenzenes with three or more chlorines, tetrachloroethene (PCE), or dichlorotoluene (
249 ring two phenylphosphonic acid groups, (3) a chlorin that bears a single phenylphosphonic acid group,
251 ute pioneered by Battersby to gain access to chlorins that bear two meso substituents, a geminal dime
252 cts of substituents yielded 3,13-substituted chlorins that contain a geminal dimethyl group in the py
256 Unlike most of the natural and synthetic chlorins, the Zn(II) complexes of the benzochlorin analo
257 Depending on the substituents present on the chlorin, this regioselectivity may change, but ALIE calc
259 and (19)F NMR spectra of the porphyrins and chlorins, thus providing a refined reference point for t
260 can be repurposed for PCI by conjugating the chlorin to a cell penetrating peptide, using bioorthogon
261 Excited-state energy transfer from a zinc chlorin to a free-base (Fb) chlorin occurs with a rate c
262 abeled chlorin was coupled with an unlabeled chlorin to give a dyad wherein a diphenylethyne linker s
263 what structural features are essential for a chlorin to resemble chlorophyll?" To begin to address th
264 hlorins represent the only nickel-containing chlorins to be isolated from a living system and are the
265 or studies of sparsely substituted synthetic chlorins to probe the effects of substituents yielded 3,
266 be a two-step conversion of C-alkylated zinc chlorins to zinc oxochlorins wherein the keto group is l
267 ed photosensitiser, disulfonated tetraphenyl chlorin (TPCS2a), in mediating photochemical internalisa
268 thyl]-2-devinyl pyropheophorbide-a (HPPH), a chlorin-type photosensitizer with more favorable photoph
269 exible orientation confirmed that one of the chlorin units of the dimeric structure is tilted toward
270 and DMF and exhibits intense fluorescence of chlorin upon excitation of BODIPY at approximately 500 n
271 hole/electron transfer rate observed for the chlorin versus porphyrin dyads is attributed to the fact
272 the fact that the HOMO is a(1u)-like for the chlorins versus a(2u)-like for the porphyrins; the a(1u)
276 substituents in defined positions make these chlorins well suited for a variety of applications in bi
277 ristic spectral features make these types of chlorins well suited for incorporation in synthetic mode
278 cesses forming the tetrahydrobilene and zinc chlorin were 32-72% and 27-62%, respectively, giving ove
280 l and redox properties of the 13-substituted chlorins were compared with those of isomeric 12-substit
285 f-assembled structures of semisynthetic zinc chlorins (ZnChls) in the solid state by pulsed radiolysi
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