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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 the photosensitizer meta-tetra(hydroxyphenyl)chlorin.
7 re labile toward dehydrogenation to give the 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 glet oxygen quantum yields found to the free chlorin.
14 inker spans the 10-positions of the two zinc chlorins.
15 between the isomeric 12- and 13-substituted chlorins.
16 l cations and radical anions of the examined chlorins.
17 developed for the synthesis of 7-substituted chlorins.
18 estern half provided access to 3-substituted chlorins.
19 s are versatile precursors to porphyrins and chlorins.
20 round state as is found for low-spin Fe(III) chlorins.
21 rdless of synthetic or biological origin, to chlorins.
22 nthetic tetrahydroporphyrins by reduction of chlorins.
23 s of readily prepared and oxidatively stable chlorins.
24 -fold, than with congeners that had no ortho chlorines.
25 eeds to PCDD/F congeners with less than four chlorines.
26 only strain to dehalogenate para-substituted chlorines.
27 lorines, but not doubly flanked or unflanked chlorines.
28 moving flanked para- and doubly flanked meta-chlorines.
30 cribed a new synthesis of C,D-ring symmetric chlorins 11, involving 2 + 2 condensation of bis-formyl-
33 tion of dihydrobenzoporphyrin 14 by reacting chlorin 3 with the phosphonium salt of p-methylbenzylbro
34 ing to this broadened in vitro activity, the chlorin 3-hydroxyethyl chlorophyllide a was newly identi
35 rption maximum (637-655 nm for the free base chlorins, 606-628 nm for the zinc chlorins) and intensit
36 tion of 8-phenanthrenevinylporphyrin 19 from chlorin 7 further confirmed our proposed mechanism for t
39 nitrogen isotope ratio, nitrogen content and chlorin abundance data from sediment cores with high acc
41 ta set of PCDD/F congeners with four or more chlorines along with all 209 polychlorinated biphenyl (P
42 porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2-oxachlorin
43 The morpholinochlorins, a class of stable chlorin analogues, were synthesized in two to three step
44 S, i.e., dipole-dipole) coupling in the ZnFb-chlorin and -oxochlorin dyads is enhanced relative to th
45 s of readily prepared and oxidatively stable chlorin and bacteriochlorin analogues with tunable optic
49 and various spectral characteristics of the chlorin and oxochlorin building blocks provide the found
51 ates and diminished efficiencies in the ZnFb chlorin and oxochlorin dyads versus the ZnFb porphyrin d
54 l window between that of analogous synthetic chlorins and 13(1)-oxophorbines (603-687 nm) and bacteri
59 free base chlorins, 606-628 nm for the zinc chlorins) and intensity of the chlorin Q(y)() band (epsi
60 ylene linker at the 13- or 3,13-positions of chlorin, and a second type where BODIPY is attached at t
61 sence of fused anhydride rings in porphyrin, chlorin, and bacterichlorin systems showed a significant
62 The ring-current strengths of the porphins, chlorins, and bacteriochlorins are 1.5-2.5 times stronge
63 The structures of the isolated porphyrins, chlorins, and bacteriochlorins, related to Bchl a, were
64 single regioisomers of diversely substituted chlorins, and in every case, the 2 + 2 condensation is a
66 the ethylene moiety from those in which the chlorines are located on the aromatic ring with the meth
67 we can distinguish the isomers in which the chlorines are located on the ethylene moiety from those
68 oxidatively dechlorinated, whereas the other chlorines are removed by a reductive process in which ch
71 the synthesis and characterization of BODIPY-chlorin arrays containing a chlorin subunit, with tunabl
74 posed of a common red-absorbing (645-646 nm) chlorin, as an energy donor, and a different near-IR emi
76 The arrays vary the tetrapyrrole (porphyrin, chlorin, bacteriochlorin), chromophore (boron-dipyrrin,
77 and optical properties of a series of novel chlorin-bacteriochlorin energy transfer dyads are descri
78 efficient energy transfer (>/=0.77) even for chlorin-bacteriochlorin pairs with large (up to 122 nm)
81 reatment strategy that combines PDT by a new chlorin-based nanoscale metal-organic framework (nMOF),
82 report here the rational design of the first chlorin-based nanoscale metal-organic framework (NMOF),
83 se amine complex, it was considered that the chlorin-based photosensitizers could be introduced into
88 ated with the preparation of ten new hangman chlorins bearing a xanthene backbone and a pendant carbo
90 hes have been developed for the synthesis of chlorins bearing formyl groups: (1) reaction of an aceta
91 te has been exploited to construct nine zinc chlorins bearing substituents at the 3- and 13-positions
92 o-flask process was applied to form six zinc chlorins bearing substituents such as pentafluorophenyl,
94 ase chlorins have been prepared wherein each chlorin bears a geminal dimethyl group in the reduced ri
95 d methodology for preparing meso-substituted chlorin building blocks and now present methodology for
97 ments introduced enable 100-mg quantities of chlorin building blocks to be prepared in a facile and r
100 preferentially dehalogenated singly flanked chlorines, but not doubly flanked or unflanked chlorines
101 gave BC-1 (53% yield) along with a trace of chlorin byproduct (1.4% relative to BC-1 upon fluorescen
102 ks in the synthesis of porphyrins, corroles, chlorins, calix[4]pyrroles, porphodimethenes, BODIPY dye
103 d to illuminate the scope to which synthetic chlorins can serve as surrogates for chlorophylls and be
105 f singlet oxygen produced by the sensitizers chlorin (Chl) and 5,10,15,20-tetrakis(N-methyl-4-pyridyl
107 des an access for novel carbon-carbon linked chlorin-chlorin dimers and chlorin-porphyrin dimers with
108 gher numbers of PEG groups, with the tri-PEG chlorin conjugate showing the best overall ovarian cance
111 he PEG groups in the mono-, di-, and tri-PEG chlorin conjugates increased the water solubility and se
112 chanism is suggested for the di- and tri-PEG chlorin conjugates; however, a more complicated process
113 oporphyrin, whereas a 13(1)-oxophorbine is a chlorin containing an annulated oxopentano ring spanning
114 pinacol-pinacolone conditions, vic-dihydroxy chlorins containing 4-methoxyphenyl or 3,5-dimethoxyphen
115 N,N'-nucleophiles failed to either generate chlorins containing a beta,beta'-dihydroxypyrroline, a p
116 actose-conjugated purpurinimides (a class of chlorins containing a six-membered fused imide ring syst
123 the natural abundance and (13)C-labeled zinc chlorin dyads and benchmark zinc chlorin monomers reveal
125 stigations reveal that the 17(3)-substituted chlorin e(6) conjugates are L-shaped, the 15(2) and 13(1
128 new water-soluble conjugate, consisting of a chlorin-e(6) photosensitizer part, a 4-arylaminoquinazol
130 sign, MnO2 nanosheets adsorb photosensitizer chlorin e6 (Ce6), protect it from self-destruction upon
131 rombin aptamer and covalently linked it with Chlorin e6 (Ce6), which is a second generation photosens
133 mic therapy (PDT) was developed by designing chlorin e6 (Ce6)-containing macromolecules, which are se
135 1c1c7 cultures presensitized with N-aspartyl chlorin e6 (NPe6) caused lysosomal disruption and apopto
136 complex system composed of PEG-PLL(-g-Ce6) [Chlorin e6 grafted poly(ethylene glycol)-poly(l-lysine)]
138 In our diagnostic approach, we evaluated Chlorin e6 polyvinylpyrrolidone (Ce6-PVP)-based fluoresc
139 we demonstrate that such a photosensitiser, chlorin e6, can be repurposed for PCI by conjugating the
141 umulate an exogenous chlorophyll derivative, chlorin e6, that renders them as sensitive to red light
142 es were prepared between the photosensitizer chlorin(e6) and various proteins (albumin, fibrinogen, a
143 fter i.v. injection of the polyanionic 17.1A chlorin(e6) conjugate or unconjugated photosensitizer.
145 onic charge had both a higher absolute tumor chlorin(e6) content and a greater tumor:normal liver rat
146 re conducted with the same MAb conjugated to chlorin(e6) followed by illumination to reduce expressio
147 etylated conjugate between poly-l-lysine and chlorin(e6) increased the relative phototoxicity in vitr
148 ith additional albumin added (2.5 protein to chlorin(e6) molar ratio) showed significantly higher wel
151 r detection or a photochemically active dye (chlorin(e6)) for therapy of early premalignancy in the h
152 body 17.1A conjugated to the photosensitizer chlorin(e6), and (b) to compare the tumor response after
153 s with BODIPY attached at the 10-position of chlorin exhibit a bright fluorescence in a range of solv
154 ere BODIPY is attached at the 10-position of chlorin exhibit approximately 5-fold brighter fluorescen
155 tached at the 3- or at both 3,13-positons of chlorin exhibit significant reduction of fluorescence in
162 n of the position of the substituents (i.e., chlorines for PCBs and alkyl groups for alkylated-PAHs)
163 ogies provide expanded access to an array of chlorins for SAR studies that may advance the effectiven
164 , this study provides access to finely tuned chlorins for spectroscopic studies and diverse applicati
168 The formation of a bis-chromene-annulated chlorin from the bacteriochlorins is also described, inc
169 respectively, giving overall yields of zinc chlorin from the Eastern and Western halves of 12-45%.
170 s-chromene-annulated meso-(pentafluorophenyl)chlorins from meso-tetrakis(pentafluorophenyl)porphyrins
171 es for a rational, step-by-step synthesis of chlorins from readily available pyrrole precursors.
173 The dominant method for the synthesis of chlorins has entailed the derivatization of porphyrins.
178 ent, a geminal dimethyl group to lock in the chlorin hydrogenation level, and no flanking meso and be
179 nts, a geminal dimethyl group to lock in the chlorin hydrogenation level, and no flanking meso and be
183 the ring A of spirochlorin and the ring C of chlorin in our model dimer 9 mimic the ring A-ring A int
186 m this series indicate that ADAMs containing chlorines in the aromatic rings might bind to HIV-1 reve
189 With both ring-B reduced and ring-D reduced chlorins in hand, their photophysical and electrochemica
190 hotophysical properties of the water-soluble chlorins in phosphate-buffered saline solution (pH 7.4)
192 nerating chromene-annulated pyrrole-modified chlorins incorporating oxazolone and morpholine moieties
196 nochromene-annulated meso-(pentafluorophenyl)chlorin is susceptible to a regioselective OsO4-mediated
197 sitions are the most toxic, removal of these chlorines is advantageous, but previous studies have onl
204 hromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochl
205 is and fluorescence spectra) of the (metallo)chlorin-like chromophores that possess slightly red-shif
206 together, the synthesis of >1000 chlorins or chlorin-like compounds (containing >50 distinct pyrrolin
208 with a fixed chain length (n) and number of chlorines (m) are referred to as a "congener group" CnCl
210 ly of the AD and BC halves, forming both the chlorin macrocycle and the isocyclic ring in a single-fl
211 yrroles that are derived from opening of the chlorin macrocycle by the Rieske-type oxygenase PHEOPHOR
212 ing in the conformational flexibility of the chlorin macrocycle direct the reactions toward the forma
213 installation (pre- and post-formation of the chlorin macrocycle) and position of the xanthene backbon
214 duce a (13)C label at the 19-position of the chlorin macrocycle, which is a site of large electron/ho
217 (>/=0.80) energy transfer from BODIPY to the chlorin moiety in both toluene and DMF and exhibits inte
218 abeled zinc chlorin dyads and benchmark zinc chlorin monomers reveal that the time scale for hole/ele
224 sfer from a zinc chlorin to a free-base (Fb) chlorin occurs with a rate constant of (110 ps)(-1) and
225 der goal of synthesizing fully non-symmetric chlorins of general structure 15, which requires regiose
229 designated sites about the perimeter of the chlorin or 13(1)-oxophorbine macrocycle is essential for
230 carbonyl)-enediyne linker in hydroporphyrin (chlorin or bacteriochlorin) dyads leads to thermally sta
232 duction of a third aryl substituent into the chlorin or oxochlorin causes an approximately 5-nm red s
234 zed for certain compounds bearing either two chlorines or two fluorines, and two methoxy groups gave
235 arrays containing PEG-substituted BODIPY and chlorins or bacteriochlorins were prepared and their opt
243 ation affects membrane biophysics, we used a chlorin photosensitizer to oxidize vesicles of various l
244 ly includes six RC chromophores and both the chlorin phytol chains and the amino acid residues <6 ang
246 bon-carbon linked chlorin-chlorin dimers and chlorin-porphyrin dimers with fixed and flexible orienta
247 or bromination of a 5,10-diaryl-substituted chlorin proceeded with high regioselectivity, affording
248 on, and mass and NMR spectrometry as an iron chlorin product formed from the saturation of the double
251 for the zinc chlorins) and intensity of the chlorin Q(y)() band (epsilon up to 79 000 M(-)(1) cm(-)(
254 sential for photosynthesis, is composed of a chlorin ring and a geranylgeranyl diphosphate (GGPP)-der
255 tion of a transmembrane helix by a lipid and chlorin ring, (ii) lipid and beta-car connection of peri
257 zation of BODIPY-chlorin arrays containing a chlorin subunit, with tunable deep-red (641-685 nm) emis
258 alkyloxazolochlorins are compared to regular chlorins, such as 2,3-dihydroxychlorins and nonalkylated
259 mpared with those of isomeric 12-substituted chlorins, synthesized previously via a 7,9-dibromo-1-for
260 s the entire history since the beginnings of chlorin synthetic chemistry in the early 20th century th
261 ain to use chlorobenzenes with three or more chlorines, tetrachloroethene (PCE), or dichlorotoluene (
262 ring two phenylphosphonic acid groups, (3) a chlorin that bears a single phenylphosphonic acid group,
264 ute pioneered by Battersby to gain access to chlorins that bear two meso substituents, a geminal dime
265 cts of substituents yielded 3,13-substituted chlorins that contain a geminal dimethyl group in the py
269 Unlike most of the natural and synthetic chlorins, the Zn(II) complexes of the benzochlorin analo
270 Depending on the substituents present on the chlorin, this regioselectivity may change, but ALIE calc
272 and (19)F NMR spectra of the porphyrins and chlorins, thus providing a refined reference point for t
273 can be repurposed for PCI by conjugating the chlorin to a cell penetrating peptide, using bioorthogon
274 Excited-state energy transfer from a zinc chlorin to a free-base (Fb) chlorin occurs with a rate c
275 abeled chlorin was coupled with an unlabeled chlorin to give a dyad wherein a diphenylethyne linker s
276 what structural features are essential for a chlorin to resemble chlorophyll?" To begin to address th
277 hlorins represent the only nickel-containing chlorins to be isolated from a living system and are the
279 or studies of sparsely substituted synthetic chlorins to probe the effects of substituents yielded 3,
280 be a two-step conversion of C-alkylated zinc chlorins to zinc oxochlorins wherein the keto group is l
281 ed photosensitiser, disulfonated tetraphenyl chlorin (TPCS2a), in mediating photochemical internalisa
282 thyl]-2-devinyl pyropheophorbide-a (HPPH), a chlorin-type photosensitizer with more favorable photoph
283 ort here hitherto unavailable eight-membered chlorin-type PMPs using an inverted "mending and breakin
284 exible orientation confirmed that one of the chlorin units of the dimeric structure is tilted toward
285 and DMF and exhibits intense fluorescence of chlorin upon excitation of BODIPY at approximately 500 n
286 hole/electron transfer rate observed for the chlorin versus porphyrin dyads is attributed to the fact
287 the fact that the HOMO is a(1u)-like for the chlorins versus a(2u)-like for the porphyrins; the a(1u)
291 substituents in defined positions make these chlorins well suited for a variety of applications in bi
292 ristic spectral features make these types of chlorins well suited for incorporation in synthetic mode
293 cesses forming the tetrahydrobilene and zinc chlorin were 32-72% and 27-62%, respectively, giving ove
295 l and redox properties of the 13-substituted chlorins were compared with those of isomeric 12-substit
299 een developed in order to synthesize hangman chlorins, which differ with regard to the order of the i
300 f-assembled structures of semisynthetic zinc chlorins (ZnChls) in the solid state by pulsed radiolysi