Bacteriochlorin-containing triad: Structure and photophysical properties

Grin, Mikhail A.; Toukach, Filip V.; Цветков, В. Б.; Reshetnikov, Roman I.; Харитонова, О. В.; Kozlov, A. S.; Krasnovsky, А.А.; Mironov, A. F.

doi:10.1016/j.dyepig.2015.04.034

Cited by 9 publications

(8 citation statements)

References 27 publications

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“…The mechanism responsible for photobleaching of BODIPY-hydroporphyrin arrays is unknown, it might be associated with the singlet oxygen production by hydroporphyrins, 6 or putative PET which leads to the oxidative degradation of hydroporphyrins.…”

Section: Resultsmentioning

confidence: 99%

“…5 Of particular interest are ET arrays with acceptors emitting in the deep-red or near-infrared spectral window, as they can be potentially used for deep-tissue in vivo imaging. 3,6 We employed hydroporphyrins (chlorins and bacteriochlorins) as fluorescent entities in energy transfer arrays, due to their favorable properties for certain bioimaging applications. 3,7 Hydroporphyrins possess narrow (FWHM < 25 nm) deep-red or near-IR emission bands, of which the maximum can be precisely tuned across a broad range (650 – 820 nm), by a variety of structural modifications.…”

Section: Introductionmentioning

confidence: 99%

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Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

et al. 2017

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BODIPY-hydroporphyrin energy transfer arrays allow for development of family of fluorophores featuring a common excitation band at 500 nm, tunable excitation band in deep red/near-infrared window, and tunable emission. Their biomedical applications are contingent upon retaining their optical properties in aqueous environment. Amphiphilic arrays containing PEG-substituted BODIPY and chlorins or bacteriochlorins were prepared and their optical and fluorescence properties were determined in organic solvents and aqueous surfactants. The first series of arrays contains BODIPYs with PEG substituents attached to the boron, whereas in the second series, PEG substituents are attached to the aryl at the meso positions of BODIPY. For both series of arrays, excitation of BODIPY at 500 nm results in an efficient energy transfer to and bright emission of hydroporphyrin in deep-red (640–660 nm) or near-infrared (740–760 nm) spectral windows. In aqueous non-ionic surfactants (Triton X-100 and Tween 20) arrays from the second series exhibit significant quenching of fluorescence, whereas properties of arrays from the first series are comparable to those observed in polar organic solvents. Reported arrays possess large effective Stokes shift (115 – 260 nm), multiple excitation wavelengths, and narrow, tunable deep-red/near-IR fluorescence in aqueous surfactants, and are promising candidates for a variety of biomedical-related applications.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

et al. 2017

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“…[14][15][16][17] To overcome this difficulty a new approach which consists of the construction of bifunctional systems combining modalities of a PS and a diagnostic agent (so called theranostics) has been developed. [18][19][20][21][22] In such systems, a fluorescent moiety can be excited selectively and independently from the photosensitizer unit enabling fluorescence imaging without toxic effects. Thus, Pandey and coworkers have used cyanine dyes as fluorescent labels to prepare conjugates with PSs.…”

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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“…Such arrays are rather rare. 15–18 For example, we 17 and others 15,16 previously studied chlorin-bacteriochlorin arrays as fluorophores with absorption and emission in deep red and emission in near-IR windows. Distyryl-BODIPYs usually possess comparable or higher absorption coefficient than chlorins (~ 100,000 M −1 ·cm −1 for distyryl-BODIPY 25 vs. 75,000 – 80,000 M −1 · cm −1 for chlorin 15 ) comparable, or longer wavelength absorption bands, are significantly easier to synthesize than chlorins, and, similarly to chlorins, are efficient energy donors to bacteriochlorins.…”

Section: Discussionmentioning

confidence: 99%

“…14 However, there are only a handful of ET arrays with both donor and acceptor absorbing in these spectral windows. 15–18 …”

Section: Introductionmentioning

confidence: 99%

BODIPY–Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands

2017

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A series of energy transfer arrays, comprising of a near-IR absorbing and emitting bacteriochlorin, and BODIPY derivatives with different absorption bands in the visible region (503 – 668 nm) have been synthesized. Absorption band of BODIPY was tuned by installation of 0, 1, or 2 styryl substituents [2-(2,4,6-trimethoxyphenyl)ethenyl], which leads to derivatives with absorption maxima at 503 nm, 587 nm, and 668 nm, respectively Efficient energy transfer (>0.90) is observed for each dyad, which is manifested by nearly exclusive emission from bacteriochlorin moiety upon BODIPY excitation. Fluorescence quantum yield of each dyad in non-polar solvent (toluene) is comparable with that observed for corresponding bacteriochlorin monomer, and is significantly reduced in solvent of high dielectric constants (DMF), most likely by photoinduced electron transfer. Given the availability of diverse BODIPY derivatives, with absorption in 500–700 nm, BODIPY-bacteriochlorin arrays should allow for construction of near-IR emitting agents with multiple and broadly tunable absorption bands. Solvent-dielectric constants dependence of Φf in dyads gives an opportunity to construct environmentally-sensitive fluorophores and probes.

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Bacteriochlorin-containing triad: Structure and photophysical properties

Cited by 9 publications

References 27 publications

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

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

BODIPY–Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands

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