Публикации

Chemoselective detection of ag+ in purely aqueous solution using fluorescence "turn-on" probe based on crowm-containing 4-methoxy-1,8-naphthalimide / P. A. Panchenko, A. S. Polyakova, Y. V. Fedorov, O. A. Fedorova // Mendeleev Communications. — 2019. — Vol. 29. — P. 155–157. [ DOI ]

Synthesis, structure and metal ion coordination of novel benzodiazamacrocyclic ligands bearing pyridyl and picolinate pendant side-arms / P. A. Panchenko, A. D. Zubenko, E. Y. Chernikova et al. // New Journal of Chemistry. — 2019. [ DOI ]

Thiourea modified doxorubicin: A perspective ph-sensitive prodrug / O. O. Krasnovskaya, V. M. Malinnikov, N. S. Dashkova et al. // Bioconjugate Chemistry. — 2019. — Vol. 30, no. 3. — P. 741–750. A novel approach to the synthesis of pH-sensitive prodrugs has been proposed: thiourea drug modification. Resulting prodrugs can release the cytotoxic agent and the biologically active 2-thiohydantoin in the acidic environment of tumor cells. The concept of acid-catalyzed cyclization of thioureas to 2-thiohydantoins has been proven using a FRET model. Dual prodrugs of model azidothymidine, cytotoxic doxorubicin, and 2-thiohydantoin albutoin were obtained, which release the corresponding drugs in the acidic environment. The resulting doxorubicin prodrug was tested on prostate cancer cells and showed that the thiourea-modified prodrug is less cytotoxic (average IC50 ranging from 0.5584 to 0.9885 μM) than doxorubicin (IC50 ranging from 0.01258 to 0.02559 μM) in neutral pH 7.6 and has similar toxicity (average IC50 ranging from 0.4970 to 0.7994 μM) to doxorubicin (IC50 ranging from 0.2303 to 0.8110 μM) under mildly acidic conditions of cancer cells. Cellular and nuclear accumulation in PC3 tumor cells of Dox prodrug is much higher than accumulation of free doxorubicin. [ DOI ]

Ultrathin film sensory system based on resonance energy transfer between non-covalently linked fluorophores / A. V. Shokurov, A. V. Alexandrova, I. I. Shepeleva et al. // Mendeleev Communications. — 2019. — Vol. 29. — P. 74–76. For the first time, we developed a proof-of-concept FRET-based sensory ultrathin film system, where planar energy donor and energy acceptor layers are not chemically bound to each other. It was shown that this approach is as feasible as the case of covalently linked FRET-couple. Its implementation opens up possibilities for development of novel sensor devices, where tedious and complicated synthesis of fluorophore couples is not required. Moreover, as was shown earlier, in such systems, FRET efficiency can be fine-tuned by introduction of spacer interlayers18, further improving proposed multilayer design. [ DOI ]

Краунсодержащие производные 4-метокси-1,8-нафталимида в качестве основы для разработки флуоресцентных РЕТ-хемосенсоров на катионы металлов / П. А. Панченко, Н. В. Лейчу, Ю. В. Федоров, О. А. Федорова // Макрогетероциклы. — 2019. [ DOI ]

A nanohybrid for photodynamic therapy and fluorescence imaging tracking without therapy / L. Francés-Soriano, M. A. Zakharko, M. González-Béjar et al. // Chemistry of Materials. — 2018. — Vol. 30. — P. 3677–3682. [ DOI ]

Complexation of a crown-substituted naphthalimide derivative with heavy metals in langmuir monolayers / I. I. Shepeleva, A. V. Shokurov, L. B. Bogdanova et al. // Russian Chemical Bulletin. — 2018. — Vol. 67, no. 12. — P. 2259–2261. It was demonstrated that, in contrast to a solution in an organic solvent, the relaxation of the excited state of a fluorophore moiety proceeds mainly radiationless upon the formation of naphthalimide fluoroionophore complexes with complementary cations in a monolayer at air-water interface. Apparently, this is due to the fact that at the air—water interface the distribution of the energy levels of molecular orbitals in the fluoroionophore complexes with cations change in such a way that relaxation of the excited state via charge transfer within the complex molecule remains possible. [ DOI ]

Nonradiative energy transfer in mixed langmuir monolayers and langmuir—blodgett films of compounds of different chemical composition and structure / I. I. Shepeleva, A. V. Shokurov, N. V. Konovalova et al. // Russian Chemical Bulletin. — 2018. — Vol. 67, no. 12. — P. 2159–2163. The efficiency of the Förster resonance energy transfer (FRET) in a monolayer film containing the energy donor and energy acceptor fluorophores is low since the energy transfer process occurs in one plane only. As the number of layers increases to five, the energy transfer efficiency increases due to the interlayer energy transfer occurring in three dimensions. Further increase in the number of layers (up to 10) causes no significant increase in the efficiency since in this case the total film thickness exceeds an optimum value for the FRET process. [ DOI ]

Panchenko P. A., Fedorov Y. V., Fedorova O. A. Selective fluorometric sensing of hg2+ in aqueous solution by the inhibition of pet from dithia-15-crown-5 ether receptor conjugated to 4-amino-1,8-naphthalimide fluorophore // Journal of Photochemistry and Photobiology A: Chemistry. — 2018. — Vol. 364. — P. 124–129. [ DOI ]

Безызлучательный перенос энергии в смешанных монослоях Ленгмюра и пленках Ленгмюра—Блоджетт соединений различного химического состава и строения / И. И. Шепелева, А. В. Шокуров, Н. В. Коновалова и др. // Известия Академии наук. Серия химическая. — 2018. — № 12. — С. 2159–2163.

Захарко М. А., Панченко П. А., Федорова О. А. Изучение влияния природы спейсерной группы на эффективности переноса энергии в конъюгатах бактериохлорина и нафталимида // Успехи в химии и химической технологии. — 2018. — Т. 32, № 5. — С. 76–78.

Комплексообразование краун-замещенного производного нафталимида с тяжелыми металлами в монослоях Ленгмюра / И. И. Шепелева, А. В. Шокуров, Л. Б. Богданова и др. // Известия Академии наук. Серия химическая. — 2018. — № 12. — С. 2259–2261.

Синтез fret-пары нафталимид-флуоресцеин и изучение процесса переноса энергии в системе / П. А. Игнатов, М. А. Захарко, П. А. Панченко, О. А. Федорова // Успехи в химии и химической технологии. — 2018. — Т. 32, № 5. — С. 91–93.

Синтез и сенсорные свойства производного дитиакраунсодержащего 4-метоксинафталимида / А. С. Полякова, П. А. Панченко, Ю. В. Федоров, О. А. Федорова // Успехи в химии и химической технологии. — 2018. — Т. 32, № 7. — С. 80–82.

A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging / P. A. Panchenko, M. A. Grin, O. A. Fedorova et al. // Physical Chemistry Chemical Physics. — 2017. — Vol. 19. — P. 30195–30206. [ DOI ]

Controlling photophysics of styrylnaphthalimides through tict, fluorescence and e,z-photoisomerization interplay / P. A. Panchenko, A. N. Arkhipova, O. A. Fedorova et al. // Physical Chemistry Chemical Physics. — 2017. — Vol. 19, no. 3. — P. 1244–1256. The photophysical properties of naphthalimide dyes NI1–3 with electron releasing 4-methoxy- (NI1), 3,4-dimethoxystyryl- (NI2) and dimethylaminostyryl (NI3) groups are examined in a variety of protic and aprotic solvents. All compounds demonstrate positive solvatochromism in the steady-state absorption and fluorescence spectra. The analysis of the dependence of the Stokes shift on the polarity of the solvent using the Lippert–Mataga equation allowed us to determine the change in the dipole moment upon excitation. The obtained data correspond to the formation of highly polar charge transfer states. Based on the transient absorption spectra and time-resolved fluorescence measurements, the presence of two different emissive states was definitely proved. The primarily formed planar Local Excited (LE) state dominates in non-polar solvents like cyclohexane and toluene where it relaxes mostly through fluorescence and E,Z-isomerisation pathways. In polar solvents, an alternative relaxation channel emerges that consists of twisting around single bond between styryl and naphthalimide fragments, which leads to the formation of a Twisted Intramolecular Charge Transfer (TICT) state. The factors affecting the fluorescence of TICT states are discussed. The observed spectral effects are rationalized using quantum-chemical calculations, X-ray data and NMR spectroscopy. [ DOI ]

Relationship between the photochromic and fluorescent properties of 4-styryl derivatives of n-butyl-1,8-naphthalimide / A. N. Arkhipova, P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova // Mendeleev Communications. — 2017. — Vol. 27, no. 1. — P. 53–55. [ DOI ]

Synthesis of 4-nitro-n-phenyl-1,8-naphthalimide annulated to thia- and azacrown ether moieties / A. S. Oshchepkov, M. S. Oshchepkov, A. N. Arkhipova et al. // SYNTHESIS-STUTTGART. — 2017. — Vol. 49. — P. 2231–2240. [ DOI ]

Synthesis, optical characteristics and complex formation of molecular receptors based on 1,8-naphthalimide derivatives in solution and in composition of hybrid tin dioxide nanoparticles / A. N. Arkhipova, P. A. Panchenko, N. E. Schepel et al. // Макрогетероциклы. — 2017. — Vol. 10, no. 1. — P. 84–93. [ DOI ]

Харченко Д. С., Панченко П. А., Федорова О. А. Комплексообразующие свойства n-фенилазадитиа-15-краун-5-эфирсодержащего производного 4-аминонафталимида с катионами металлов // Успехи в химии и химической технологии. — 2017. — Т. 31, № 12. — С. 75–77.

Разработка оптического сенсора на анионы на основе азометинового производного 1,8-нафталимида / П. А. Игнатов, М. А. Захарко, П. А. Панченко, О. А. Федорова // Успехи в химии и химической технологии. — 2017. — Т. 31, № 12. — С. 54–56.

Синтез и исследование оптических свойств конъюгата бактериохлорина и красителя на основе нафталимида для комбинированной фотодинамической терапии и флуоресцентной диагностики рака / М. А. Захарко, А. Н. Архипова, П. А. Панченко, О. А. Федорова // Успехи в химии и химической технологии. — 2017. — Т. 31, № 12. — С. 45–47.

Synthesis and spectral properties of fluorescent dyes based on 4-styryl-1,8-naphthalimide / P. A. Panchenko, A. N. Arkhipova, M. A. Zakharko et al. // Russian Chemical Bulletin. — 2016. — Vol. 65, no. 10. — P. 2444–2451. [ DOI ]

Utilizing a ph-sensitive dye in the selective fluorescent recognition of sulfate / A. M. Agafontsev, T. A. Shumilova, P. A. Panchenko et al. // Chemistry - A European Journal. — 2016. — Vol. 22, no. 42. — P. 15069–15074. A receptor containing amidopyrrole binding subunits and free amino groups, conjugated to a naphthalimide dye, has been designed and synthesized. The intrinsic selectivity of the binding motif for phosphate present in DMSO completely disappears in 10% DMSO aqueous buffer at pH 3.6, at which the receptor is protonated. The electrostatic interactions between the receptor and an anion start to dominate, thus leading to selectivity for sulfate. The ability of the HSO4- anion to transfer the proton to the amino group during the recognition event suppresses the photoinduced electron transfer (PET) on the dye, resulting in a selective turn-on fluorescent response. The choice of pH of the solution for sensing is dictated by the pKa value of the dye. [ DOI ]

Синтез новых стириловых производных 1,8-нафталимида / М. А. Захарко, А. Н. Архипова, П. А. Панченко, О. А. Федорова // Успехи в химии и химической технологии. — 2016. — Т. 30, № 11. — С. 33–35.

Cation-dependent spectral properties of fluorescent complexon based on 1,8-naphthalimide with pet mechanism of optical response / P. A. Panchenko, V. V. Park, O. A. Fedorova et al. // Russian Chemical Bulletin. — 2015. — Vol. 64, no. 8. — P. 1871–1876. Complexation of 4-amino-1,8-naphthalimide derivative containing an aza-15-crown-5 ether receptor unit in the N-aryl substituent at the imide nitrogen atom of the naphthalimide core with alkaline earth metal cations was studied using optical and NMR spectroscopy. The binding of the cations with crown ether receptors was accompanied by signifacant fluorescence enhancement of naphthalimide moiety caused by the inhibition of the photoinduced electron transfer (PET) process. An increase in the cation radii on going from Mg2+ to Ca2+ to Ba2+ leads to a decrease in the complex stability and an increase in the quantum yield of its fluorescence. [ DOI ]

Fret versus pet: ratiometric chemosensors assembled from naphthalimide dyes and crown ethers / P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova, J. Gediminas // Physical Chemistry Chemical Physics. — 2015. — Vol. 17, no. 35. — P. 22749–22757. Novel bi-chromophoric naphthalimide derivatives containing benzo-15-crown-5 and N-phenyl-aza-15- crown-5 receptor moieties BNI2 and BNI3 were designed and prepared. Significant Fo ¨rster resonance energy transfer (FRET) from donor (D) amido-naphthalimide to acceptor (A) amino-naphthalimide chromophores as well as photoinduced electron transfer (PET) between the N-aryl receptor and amido- naphthalimide fragment was revealed by the steady-state and time-resolved UV/Vis absorption and fluorescence spectroscopy. Upon the addition of alkaline-earth metal perchlorates to an acetonitrile solution of ligands, FRET mediated fluorescence enhancement was observed, which was a result of inhibition of the PET competitive deactivation pathway. The studied compounds provide an opportunity to register a two-channel fluorescence response upon selective excitation of either of the photoactive units and, thus, might be of interest as ratiometric probes. [ DOI ]

Isomeric naphthalimides bearing pyran units: Insight into mutual relation between structure and photochromic properties / O. A. Fedorova, A. N. Sergeeva, P. A. Panchenko et al. // Journal of Photochemistry and Photobiology A: Chemistry. — 2015. — Vol. 303. — P. 28–35. [ DOI ]

Panchenko P. A., Fedorova O. A., Fedorov Y. V. Fluorescent and colorimetric chemosensors for cations based on 1,8-naphthalimide derivatives: design principles and optical signalling mechanisms // Russian Chemical Reviews. — 2014. — Vol. 83, no. 2. — P. 155–182. [ DOI ]

Intra- and interlayer energy transfer in planar systems based on amphiphilic naphthalimide derivatives / S. L. Selector, L. B. Bogdanova, A. V. Shokurov et al. // Макрогетероциклы. — 2014. — Vol. 7, no. 3. — P. 311–320. The present work considers the possibility of increasing the information signal of thin-film sensitive element of the sensor based on amphiphilic crown substituted derivative of 4-(acylamino)-1,8-naphthalimide via employment of resonance photoexcitation energy transfer process. In such system, information signal is the fluorescence of acceptor fluorophore (4-alkylamino-1,8-naphthalimide), which is excited upon non-radiative transfer of the energy from excited donor fluorophore (crown containing derivative of 4-(acylamino)-1,8-naphthalimide), crown ether fragment of which is “occupied” by coordination interaction with specific cation and thus does not participate in rapid relaxation of the excitation by the photoinduced electron transfer mechanism. For realization of this goal, the synthesis of novel amphiphilic naphthalimide derivatives is carried out; conditions for obtaining of stable monolayers and Langmuir-Blodgett films based on them are studied. It is established that azadithiacrown substituted amphiphilic fluoroionophore in monolayers at air/mercury and silver perchlorate aqueous solutions interface retains the ability for efficient binding of Ag+ and Hg2+ known for its solutions. Described principle of generation of fluorescent signal using mixed monolayer containing the donor-acceptor couple allows one to increase the value of optical response of the monolayer to the presence of assessed cations by 2.5 times. However, the monolayer fluorescence intensity remains too low for practical application. In order to optimize the conditions of the energy transfer process in more practically important solid-state sensory elements we studied the mechanism of non-radiative photoexcitation energy transfer in the multilayer thin-film system based on amphiphilic naphthalimide derivatives obtained by Langmuir-Blodgett (LB) technique. It is shown that this problem can be solved by regulation of the distance between donor and acceptor layers of LBF. Optimal thickness of the separating layer of stearic acid, which for this system amounted to 7 nm, was determined experimentally. Obtained results open up new perspectives for increase of the information signal reading efficiency, which should find application in development of sensitive elements of sensor devices. [ DOI ]

Spectroscopical study of bacteriopurpurinimide-naphthalimide conjugates for fluorescent diagnostics and photodynamic therapy / P. A. Panchenko, A. N. Sergeeva, O. A. Fedorova et al. // Journal of Photochemistry and Photobiology B: Biology. — 2014. — Vol. 133. — P. 140–144. [ DOI ]

Оптические сенсоры на катионы на основе производных 1,8-нафталимида, содержащие салицилидениминовый фрагмент / С. Д. Камагуров, П. А. Панченко, О. А. Федорова, Н. Э. Шепель // Успехи в химии и химической технологии. — 2014. — Т. 28, № 10 (159). — С. 56–59.

Синтез 4-стирилзамещенных 1,8-нафталимида для применения в качестве флуоресцентных навигаторов в фотодинамической терапии онкологических заболеваний / М. А. Захарко, А. Н. Сергеева, П. А. Панченко, О. А. Федорова // Успехи в химии и химической технологии. — 2014. — Т. 28, № 10 (159). — С. 49–51.

ФОТОАКТИВНАЯ СУПРАМОЛЕКУЛЯРНАЯ СИСТЕМА НА ОСНОВЕ ФЛУОРЕСЦЕНТНОГО ПРОИЗВОДНОГО НАФТАЛИМИДА И ФОТОХРОМНОГО 18-КРАУН-6-ЭФИРСОДЕРЖАЩЕГО ПРОИЗВОДНОГО БЕНЗОПИРАНА / А. Н. Сергеева, П. А. Панченко, О. А. Федорова, Ю. В. Федоров // Успехи в химии и химической технологии. — 2014. — Т. 28, № 10. — С. 52–55.

Comparative analysis of the pet and ict sensor properties of 1,8-naphthalimides containing aza-15-crown-5 ether moiety / P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova, G. Jonusauskas // Dyes and Pigments. — 2013. — Vol. 98, no. 3. — P. 347–357. [ DOI ]

Synthesis and sensor propeties of crown-containing derivatives of 4-(1,5-diphenyl-delta(2)-pyrazolin-3-yl)-1,8-naphthalimide / A. N. Sergeeva, P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova // Protection of Metals and Physical Chemistry of Surfaces. — 2012. — Vol. 48, no. 5. — P. 524–533. [ DOI ]

Комплексообразование органического люминофора с тяжелыми металлами в монослоях Ленгмюра / Л. Б. Богданова, С. Л. Селектор, В. В. Арсланов и др. // "Структура и динамика молекулярных систем. Яльчик-2012". — Т. 2. — 2012. — С. 193–196.

Hybrid sensor materials based on tin(iv) oxide and crown-containing 4-amino-1,8-naphthalimides / P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova et al. // Mendeleev Communications. — 2011. — Vol. 21, no. 1. — P. 12–14. The cation-dependent spectral properties of crown-containing 4-aminonaphthalimide derivatives have been studied in an acetonitrile solution and within hybrid materials based on tin dioxide; these compounds can be of interest for producing fluorescent sensors for metal ions. [ DOI ]

НОВЫЕ СЕНСИБИЛИЗАТОРЫ ДЛЯ ФОТОДИНАМИЧЕСКОЙ ТЕРАПИИ РАКА НА ОСНОВЕ ПРОИЗВОДНЫХ НАФТАЛИМИДА И ПРИРОДНЫХ ХЛОРОФИЛЛОВ / А. Н. Сергеева, Р. И. Решетников, П. А. Панченко и др. // Успехи в химии и химической технологии. — 2011. — Т. 25, № 11. — С. 62–66.

СИНТЕЗ И СПЕКТРАЛЬНО-ЛЮМИНЕСЦЕНТНЫЕ СВОЙСТВА АЗАКРАУН-СОДЕРЖАЩИХНАФТАЛИМИДОВ И ИХ КОМПЛЕКСОВ С КАТИОНАМИ МЕТАЛЛОВ / А. С. Ощепков, М. С. Ощепков, П. А. Панченко и др. // Успехи в химии и химической технологии. — 2011. — Т. 25, № 4. — С. 69–74.

Синтез и сенсорные свойства краунсодержащих производных 4-пиразолинил-1,8-нафталимида / А. Н. Сергеева, П. А. Панченко, О. А. Федорова, Ю. В. Федоров // Успехи в химии и химической технологии. — 2011. — Т. 25, № 4. — С. 61–66.

Cation-dependent fluorescent properties of naphthalimide derivatives with n-benzocrown ether fragment / P. A. Panchenko, Y. V. Fedorov, V. P. Perevalov et al. // The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. — 2010. — Vol. 114, no. 12. — P. 4118–4122. [ DOI ]

Панченко П. А., Перевалов В. П., Федорова О. А. Дитиакраунсодержащие производные 4-ациламино-1,8-нафталимида в качестве флуоресцентных сенсоров на катионы металлов // Успехи в химии и химической технологии. — 2010. — Т. 24, № 2 (107). — С. 76–81. Спектрально-люминесцентные свойства производных 4-ацетиламинонафталимида, содержащих остаток бензодитиа-15-краун-5- и N-фенилазадитиа-15-краун-5-эфира в качестве N-арильного заместителя, изучены в ацетонитрильном растворе в присутствии и в от-сутствии катионов металлов. Показано, что связывание катионов ртути (II) указанными соединениями происходит селективно и сопровождается разгоранием флуоресценции. На основе азакраун-эфирного производного нафталимида получены полимерные сенсорные мембраны, способные детектировать катионы Аg+ и Hg2+ в водных растворах при концентрации порядка 10e-5 моль/л.

Synthesis and spectral properties of 4-amino- and 4-acetylamino-n-arylnaphthalimides containing electron-donating groups in the n-aryl substituent / P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova et al. // Russian Chemical Bulletin. — 2009. — Vol. 58, no. 6. — P. 1233–1240. [ DOI ]

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