- Rational design of fluorescent probes for targeted: In vivo nitroreductase visualization
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Nitroreductase (NTR) has been recognized as a biomarker for identifying the hypoxic status of cancers. Therefore, it is of high scientific interest to design effective fluorescent probes for tracking NTR activity. However, studies on elucidation of the structure-performance relationship of fluorescent probes and those providing valuable insight into optimized probe design have rarely been reported. Three BODIPY based fluorescent probes were made by conjugation of para-, ortho-, and meta-nitrobenzene to the BODIPY core via a thiolether bond, respectively. Our study revealed that the linkage and nitro substituent position significantly influence the capability of nitroreductase detection.
- Chen, Ji-An,Gao, Jie,Gu, Xianfeng,Li, Mimi,Tan, Jiahui,Yin, Xiaofan,Zhao, Zhen
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p. 4744 - 4747
(2020/07/13)
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- SPIROBODIPYs with spiropyran structure compound, preparation method and its use
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The invention discloses a SPIROBODIPYs compound with the spiropyrane structure. The compound has the following structural general formula (refer to the Specification), wherein R1, R2, R3 and R4 are alkyl substituents or aromatic substituents, R5 is an alkyl substituent, an alcohol hydroxyl substituent or a substituent with triple bonds at the tail end. The invention further discloses the application of the SPIROBODIPYs compound to a fluorescence molecular probe. The SPIROBODIPYs compound can be applied to controllable detection of physiological and pathological process of cells, and can be used for building living cell acid organelles or used as a novel fluorescent dye of a fluorescence molecular probe for detecting the acid environment of cancer cells.
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- REACTIVE LABELLING COMPOUNDS AND USES THEREOF
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Provided are azido-BODIPY compounds of formula (I), cyclooctyne-based fluorogenic probes of formula (IV), and activity-based probes of formula (VI). These compounds undergo azide alkyne cycloadditions (AAC) with to form triazolyl products. The provided compounds are useful for detection and imaging of alkyne-, or azide-containing molecules. Methods for detection and imaging biomolecules using compounds of the present disclosure are disclosed.
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- Preparation, spectral and thermal properties of Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) complexes with iodosubstituted 2,2′-dipyrrolylmethene
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Complexes [ML2] of cobalt(II), nickel(II), copper(II), zinc(II), and cadmium(II) with asymmetrically substituted (E)-3-ethyl-5-[(4-iodo-3,5- dimethyl-2H-pyrrol-2-ylidene)methyl]-2,4-dimethyl-1H-pyrrole (HL) have been prepared and characterized for the first time. The spectral properties, stability in solutions and in the solid phase at elevated temperature of the complexes have been studied. The effects of complexing metal ion and the reaction medium on the spectral luminescent properties (absorptivity, quantum yield, fluorescence lifetime, and the radiation constant) and on thermal destruction of the [ML2] complexes have been discussed.
- Guseva,Antina,Beresin,V'Yugin,Nuraneeva
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p. 1571 - 1579
(2013/10/22)
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- Synthesis and spectral properties of new 3,3'-bis(dipyrrolylmethene) with acetylene spacer
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Bis(2,4,7,9-tetramethyl-8-ethyldipyrrolylmethen-3-yl)acetylene dihydrobromide (H2L·2HBr), new bis(dipyrrolylmethene), in whose molecule dipyrrolylmethene domains were connected through 3,3'-carbon atoms of internal pyrrole nuclei by acetylene spacer, were synthesized by original procedure. The compound was characterized by element analysis, IR, 1H NMR, and electronic spectroscopy. The comparative analysis of spectral properties shows the reduction of the basicity of H2L ligand in comparison with the structural analogs, which contain internal methylene spacer. The quantum-chemical simulation showed that the rigid acetylene spacer gives linear structure to the H2L molecule in contrast to the spiral-shaped geometry of structural analogs with-CH2-spacer. Pleiades Publishing, Ltd., 2010.
- Antina,Guseva,Loginova,Semeikin,V'Yugin
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p. 2374 - 2381
(2011/04/14)
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- An efficient method for the synthesis of unsymmetrical 2,2′- bis(pyrrolyl)alkanes
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A new strategy for the preparation of unsymmetrical 2,2′- bis(pyrrolyl)alkanes has been developed. It involved the condensation of pyrrole derivatives onto N-benzylhydroxylamines in the presence of HCl. This two-step procedure provided access to a wide variety of 2,2′-dipyrromethanes (3a-m). It has also been extended to the synthesis of tripyrromethanes 4a-d and of N-confused dipyrromethanes 6a-d.
- Murat-Onana, Marie Laure,Berini, Christophe,Minassian, Frederic,Pelloux-Leon, Nadia,Denis, Jean-Noel
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body text
p. 2204 - 2211
(2010/07/04)
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- Design and development of a new pyrromethene dye with improved photostability and lasing efficiency: Theoretical rationalization of photophysical and photochemical properties
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(Chemical Equation Presented) In an attempt to develop a photostable and efficient pyrromethene compound for use in liquid dye lasers, three congeners of the commercially available pyrromethene 567 (PM567) laser dye were synthesized and their photophysical properties, lasing efficiencies, and photochemical stabilities were studied. In general the presence of an aryl group at C-8 of the pyrromethene chromophore increased the photostability. One of the congeners possessing a C-8 trimethoxyphenyl moiety showed significantly improved lasing parameters than PM567. Compared to PM567, the photochemical stability of the new dye was 2-fold, while it showed an equivalent lasing efficiency to that of PM567 at a significantly lower concentration. The increased photostability of these new dye molecules could be explained by theoretical calculation on their capacity to generate singlet oxygen (1O2) and probability of reaction with 1O2. Our calculations were in agreement with the experimental results and indicated that a systematic design of new derivatives of pyrromethene chromophore might lead to improved laser dye molecules.
- Mula, Soumyaditya,Ray, Alok K.,Banerjee, Manas,Chaudhuri, Tandrima,Dasgupta, Kamalesh,Chattopadhyay, Subrata
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p. 2146 - 2154
(2008/09/19)
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- Syntheses of per-15N labeled etioporphyrins I-IV and a related tetrahydrobenzoporphyrin for applications in organic geochemistry and vibrational spectroscopy
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Nitrogen-15 labeled pyrroles have been prepared from commercially available 15N glycine or sodium nitrite using the Barton-Zard, Knorr, and Kleinspehn approaches. These pyrroles were used as intermediates in the synthesis of per-15N labeled porphyrins needed for the analysis and assignment of vibrational spectra for sedimentary porphyrins. Etioporphyrin-I was prepared via pyrromethene intermediates, while etioporphyrins II-V and a related tetrahydrobenzoporphyrin were synthesized via stepwise routes involving the copper(II) mediated cyclization of a,c-biladienes as the key step. Detailed analyses of both the proton and carbon-13 NMR spectra provide nitrogen-15 coupling constants for these important structures.
- Lash, Timothy D.,Chen, Shaohua
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p. 11577 - 11600
(2007/10/03)
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- Thermochemistry of substituted pyrroles
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The heats of solution of a series of substituted pyrroles in benzene, carbon tetrachloride, chloroform, DMF, and pyridine were measured by a calorimetric method at 298.15 K.The influence of substituents in the pyrrole molecule on the energy parameters of solvation by organic solvents is discussed.
- Berezin, M. V.,Semeikin, A. S.,V'yugin, A. I.,Krestov, G. A.
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p. 449 - 453
(2007/10/02)
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- An efficient route to dipyrrinones: Synthesis of xanthobilirubic acid methyl ester
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Structurally interesting and complicated dipyrrinones, such as xanthobilirubic acid methyl ester (9), can be synthesized on a large scale from simple, inexpensive starting materials like ethyl acetoacetate, 2,4-pentanedione (1) and ethyl acrylate in 8 steps with an average yield of 80% at each step and an overall 17% yield.
- Shrout,Lightner
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p. 1062 - 1065
(2007/10/02)
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- The Chemistry of Pyrrolic Compounds. LXI Petroporphyrins from the Julia Creek Oil Shale: Further Evidence for the Derivation of Aetiotype Petroporphyrins from Chlorophyll
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The synthesis of the porphyrins (2c-j) has been achieved by the oxidative cyclization of appropriately substituted biladienes-ac.The availability of authentic material has allowed the finalization of the structure of a series of aetiotype fossil porphyrins which vary in substitution pattern at positions 3 and 13.All combinations of H, Me and Et at these positions have now been isolated from natural sources.This points to a common precursor, possibly a divinylporphyrin, and strengthens the belief that the chlorophylls are the prime source of the petroporphyrins.A vinyl group, or a close derivative, is found at position 3 of all chlorophylls while fragmentation of the ubiquitous isocyclic ring of the chlorophylls could yield the vinyl group at position 13.
- Clezy, Peter S.,Fookes, Christopher J. R.,Prashar, Jognandan K.
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p. 775 - 786
(2007/10/02)
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- An Improved Approach to 5'-Unsubstituted 5-Formyldipyrromethanes
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A general synthesis of 5'-unsubstituted 5-formylpyrromethanes, precursors to centrosymmetric porphyrins, is described.Cyanovinyl groups are used to protect the aldehydes and stabilize the dipyrromethanes. 5-(Chloromethyl)-2-(2,2-dicyanovinyl)pyrroles were condensed with 5-unsubstituted pyrrole-2-carboxylate ethyl esters in warm glacial acetic acid to give a series of 5'-(ethoxycarbonyl)-5-(2,2-dicyanovinyl)-2,2'-dipyrromethanes in high yield.Aqueous alkali was used to deprotect the dicyanovinyl substituent to regenerate the aldehyde and saponify the ethyl ester in a single step.The acid group was subsequently decarboxylated thermally to give the 5'-unsubstituted 5-formyl-2,2'-dipyrromethane.An alternative route was also designed by substitution of a benzyl for an ethyl ester.Hydrogenolysis released the carboxylic acid without affecting the cyanovinyl group, and the subsequent decarboxylation in neat trifluoroacetic acid accurred without rearrangement.Deprotection using aqueous alkali produced crystalline 5'-unsubstituted 5-formyldipyrromethane.The complete lack of rearrangement during the synthesis and manipulation of the dipyrromethanes was confirmed by 13C NMR spectroscopy.
- Wijesekera, Tilak P.,Paine, John B.,Dolphin, David
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p. 3832 - 3838
(2007/10/02)
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- Deacylation of Pyrrole and other Aromatic Ketones
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Ethyl 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylate (1a) reacts rapidly with ethylene glycol in refluxing benzene with p-toluenesulfonic acid or perchloric acid as a catalyst to give ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate (3) in high yield (96 percent).Various 2- and 3-acylpyrroles can be efficiently deacylated by using this procedure.Other ketones which undergo deacylation include phenyl(2-phenylindol-3-yl)methanone (19), 1-(5-methyl-1-phenylpyrazol-4-yl)ethanone (20), and 2,4-dimethoxybenzophenone.Certain pyrrole ketones where the acyl group is flanked by two ring methyl groups are also cleaved under acidic conditions by using ethanedithiol.
- Moon, M. W.,Wade, R. A.
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p. 2663 - 2669
(2007/10/02)
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- Xanthobilirubic Acid and Its Amides. Synthesis, Spectroscopy, and Solution Structures
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Xanthobilirubic acid, 5--2,4-dimethyl-1H-pyrrol-3-propanoic acid, its methyl ester, amide, N-methylamide and dimethylamide, and kryptopyrromethenone have been synthesized and characterized spectroscopically.In d6-DMSO solution all pyrromethenones were monomeric, with lactam and pyrrole N-Hs H-bonded to solvent.In deuteriochloroform, the pyrromethenones preferred a dimeric form, with intramolecular H-bonding between the lactam C=O of one unit and the lactam and pyrrole N-Hs of the second.
- Lightner, D. A.,Ma, J.-S.,Adams, T. C.,Franklin, R. W.,Landen, G. L.
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p. 139 - 144
(2007/10/02)
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- Structurel Analysis of Tetrapyrroles by Hydrogen Chemical Ionization Mass Spectrometry
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The H2 chemical ionization mass spectra of several standard porphyrins have been determined.Fragmentation proceeds via hydrogenation yielding porphyrinogens, followed by cleavage at the meso (bridge) positions to produce mono-, di-, and tripyrrolic ions.Secondary fragmentation by cleavage of substituent groups attached to the pyrrole rings may then occur.Identification of these fragments and the corresponding molecular ions produces considerable structural information on the parent molecule.In certain cases these data are sufficient to distinguish porphyrin type (positional) isomers.In addition information of substituents at meso positions may be retained.
- Shaw, George J.,Eglinton, Geoffrey,Quirke, J. Martin E.
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p. 2014 - 2020
(2007/10/02)
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