Relationship between the photochromic and fluorescent properties of 4-styryl derivatives of N-butyl-1,8-naphthalimide

Arkhipova, Antonina N.; Panchenko, Pavel A.; Fedorov, Yury V.; Федорова, О. А.

doi:10.1016/j.mencom.2017.01.016

Cited by 19 publications

(7 citation statements)

References 22 publications

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“…[35][36][37] Because of its intense fluorescence, large Stokes shifts along with the relative ease of synthetic operations for targeted modification of the molecular structure, these types of compounds have found application in the construction of fluorescent chemosensors for biologically relevant cations and anions, [38][39][40] labels or probes for proteins, cells, lysosomes and other acidic organelles. [41][42][43] In our recent papers, [44][45][46] we have described photophysical properties of naphthalimides containing a substituted styryl fragment as an electron releasing group at the 4 th position of a naphthalene ring. It has been found that the presence of the 4-(N,N-dimethylamino)styryl group extends the p-system of the parent chromophore and results in the long wavelength intramolecular charge transfer (ICT) absorption and emission, which is preferable for fluorescence imaging.…”

Section: Introductionmentioning

confidence: 99%

A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging

Panchenko

Grin

Федорова

et al. 2017

Phys. Chem. Chem. Phys.

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Propargyl-15,17-dimethoxy-13-amide of bacteriochlorin e (BChl) and a 4-(4-N,N-dimethylaminostyryl)-N-alkyl-1,8-naphthalimide bearing azide group in the N-alkyl fragment were conjugated by the copper(i)-catalyzed 1,3-dipolar cycloaddition to produce a novel dyad compound BChl-NI for anticancer photodynamic therapy (PDT) combining the modalities of a photosensitizer (PS) and a fluorescence imaging agent. A precise photophysical investigation of the conjugate in solution using steady-state and time-resolved optical spectroscopy revealed that the presence of the naphthalimide (NI) fragment does not decrease the photosensitizing ability of the bacteriochlorin (BChl) core as compared with BChl; however, the fluorescence of naphthalimide is completely quenched due to resonance energy transfer (RET) to BChl. It has been shown that the BChl-NI conjugate penetrates into human lung adenocarcinoma A549 cells, and accumulates in the cytoplasm where it has a mixed granular-diffuse distribution. Both NI and BChl fluorescence in vitro provides registration of bright images showing perfectly intracellular distribution of BChl-NI. The ability of NI to emit light upon excitation in imaging experiments has been found to be due to hampering of RET as a result of photodestruction of the energy acceptor BChl unit. Phototoxicity studies have shown that the BChl-NI conjugate is not toxic for A549 cells at tested concentrations (<8 μM) without light-induced activation. At the same time, the concentration-dependent killing of cells is observed upon the excitation of the bacteriochlorin moiety with red light that occurs due to reactive oxygen species formation. The presented data demonstrate that the BChl-NI conjugate is a promissing dual function agent for cancer diagnostics and therapy.

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Section: Introductionmentioning

confidence: 99%

A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging

Panchenko

Grin

Федорова

et al. 2017

Phys. Chem. Chem. Phys.

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“…600 nm) [ 18 ] as well as the presence of a positive charge in the pyridinium core, which is supposed to enhance water compatibility. Naphthalimides are classic fluorescent dyes whose electronic absorption and emission depend on the properties of the molecular structure and surrounding medium [ 19 , 20 , 21 , 22 ]; they have been widely applied as photoactive components in the construction of molecular devices with switchable optical characteristics [ 23 , 24 , 25 , 26 ] including fluorescent chemosensors [ 27 , 28 , 29 , 30 ]. As a receptor, we used azadithia-15-crown-5 (A15C5) ether exhibiting high affinity towards mercury (II) cations in a slightly acidic aqueous solution [ 18 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

Fluorescent RET-Based Chemosensor Bearing 1,8-Naphthalimide and Styrylpyridine Chromophores for Ratiometric Detection of Hg2+ and Its Bio-Application

et al. 2022

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Dyad compound NI-SP bearing 1,8-naphthalimide (NI) and styrylpyridine (SP) photoactive units, in which the N-phenylazadithia-15-crown-5 ether receptor is linked with the energy donor naphthalimide chromophore, has been evaluated as a ratiometric fluorescent chemosensor for mercury (II) ions in living cells. In an aqueous solution, NI-SP selectively responds to the presence of Hg2+ via the enhancement in the emission intensity of NI due to the inhibition of the photoinduced electron transfer from the receptor to the NI fragment. At the same time, the long wavelength fluorescence band of SP, arising as a result of resonance energy transfer from the excited NI unit, appears to be virtually unchanged upon Hg2+ binding. This allows self-calibration of the optical response. The observed spectral behavior is consistent with the formation of the (NI‑SP)·Hg2+ complex (dissociation constant 0.13 ± 0.04 µM). Bio-imaging studies showed that the ratio of fluorescence intensity in the 440–510 nm spectral region to that in the 590–650 nm region increases from 1.1 to 2.8 when cells are exposed to an increasing concentration of mercury (II) ions, thus enabling the detection of intracellular Hg2+ ions and their quantitative analysis in the 0.04–1.65 μM concentration range.

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“…Производные 1,8-нафталимида широко применяются как лазерные красители, [6] оптические отбеливатели, [7] имиджинговые реагенты для биологии и медицины, [8][9][10][11] противоопухолевые препараты, [12,13] фотоактивные компоненты электролюминесцентных устройств [14,15] и фотохромных материалов с переключаемыми флуоресцентными характеристиками. [16][17][18] Оптическая платформа 1,8-нафталимида является весьма популярной и для создания флуоресцентных хемосенсоров на катионы металлов. [19][20][21] Ранее нами было показано, что введение краун-эфирных рецепторов в состав N-арильного заместителя при имидном атоме азота нафталимидного ядра приводит к флуоресцентным хемосенсорам на ионы металлов, способным демонстрировать разгорание флуоресценции за счет ингибирования процесса фотоиндуцированного переноса электрона (РЕТ, англ.…”

Section: Introductionunclassified

A Study on Cation-Dependent Resonance Energy Transfer in Crown-Containing Bischromophoric System Based on 4-Methoxyand 4-Styryl-1,8-naphthalimide

Panchenko¹,

Polyakova²,

Fedorov³

et al. 2022

MHC

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С использованием медь(I)-катализируемой клик-реакции азид-алкинного 1,3-диполярного циклоприсоединения получен азадитиа-15-краун-5-содержащий бисхромофорный хемосенсор BNI, включающий фрагменты 4-алкокси-и 4-стирил-1,8-нафталимида. Возбуждение BNI светом с длиной волны 360 нм приводит к резонансному переносу энергии (RET) в системе и появлению в спектре флуоресценции полосы с максимумом 617 нм, отвечающей испусканию 4-стирилнафталимидного хромофора. Анализ стационарных спектров поглощения и флуоресценции показал, что эффективность переноса энергии (Φ RET ) в свободном лиганде BNI составляет 65%. Найденное значение Φ RET оказалось существенно ниже, чем полученное в результате теоретического расчета в рамках индукционно-резонансной модели Ферстера (99.98%). Указанное различие может быть связано с протеканием процесса фотоиндуцированного переноса электрона (PET) с рецепторной группы на возбужденный остаток 4-алкоксинафталимида, составляющего конкуренцию переносу энергии. Возможность РЕТ-процесса была подтверждена данными квантово-химических расчетов с использованием метода РМ6. Связывание катионов серебра соединением BNI в водном растворе при рН 7.4 (HEPES-буфер) сопровождалось разгоранием флуоресценции в области 620 нм, обусловленным подавлением РЕТ-взаимодействия при комплексообразовании и увеличением эффективности RET в системе. Координация катиона Ag + по краун-эфирному фрагменту BNI была продемонстрирована с использованием спектроскопии 1 Н ЯМР.Ключевые слова: Сенсор, краун-эфир, нафталимид, флуоресценция, резонансный перенос энергии (RET), фотоиндуцированный перенос электрона (PET), Ag + , комплексообразование.

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Relationship between the photochromic and fluorescent properties of 4-styryl derivatives of N-butyl-1,8-naphthalimide

Cited by 19 publications

References 22 publications

A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging

A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging

Fluorescent RET-Based Chemosensor Bearing 1,8-Naphthalimide and Styrylpyridine Chromophores for Ratiometric Detection of Hg2+ and Its Bio-Application

A Study on Cation-Dependent Resonance Energy Transfer in Crown-Containing Bischromophoric System Based on 4-Methoxyand 4-Styryl-1,8-naphthalimide

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