Spectroscopical study of bacteriopurpurinimide–naphthalimide conjugates for fluorescent diagnostics and photodynamic therapy

Panchenko, Pavel A.; Sergeeva, A. N.; Федорова, О. А.; Fedorov, Yuri V.; Reshetnikov, Roman I.; Schelkunova, Anastasiya E.; Grin, Mikhail A.; Mironov, A. F.; Jonusauskas, Gediminas

doi:10.1016/j.jphotobiol.2014.03.008

Cited by 21 publications

(13 citation statements)

References 31 publications

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“…[1] Specifically in medicine and dentistry, light has become a powerful alternative approach for non-invasive therapy and diagnosis. [2,3] Hence many pre-clinical studies employ light either for detection of pathology or to induce biological responses. There is a need to clearly understand light-tissue interactions as an important step before translation into clinical practice.…”

Section: Introductionmentioning

confidence: 99%

The optical properties of mouse skin in the visible and near infrared spectral regions

Sabino

Deana

Yoshimura

et al. 2016

Journal of Photochemistry and Photobiology B: Biology

113

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Visible and near-infrared radiation is now widely employed in health science and technology. Pre-clinical trials are still essential to allow appropriate translation of optical methods into clinical practice. Our results stress the importance of considering the mouse strain and gender when planning pre-clinical experiments that depend on light-skin interactions. Here, we evaluated the optical properties of depilated albino and pigmented mouse skin using reproducible methods to determine parameters that have wide applicability in biomedical optics. Light penetration depth (δ), absorption (µa), reduced scattering (µ's) and reduced attenuation (µ't) coefficients were calculated using the Kubelka-Munk model of photon transport and spectrophotometric measurements. Within a broad wavelength coverage (400–1400 nm), the main optical tissue interactions of visible and near infrared radiation could be inferred. Histological analysis was performed to correlate the findings with tissue composition and structure. Disperse melanin granules present in depilated pigmented mouse skin were shown to be irrelevant for light absorption. Gender mostly affected optical properties in the visible range due to variations in blood and abundance of dense connective tissue. On the other hand, mouse strains could produce more variations in the hydration level of skin, leading to changes in absorption in the infrared spectral region. A spectral region of minimal light attenuation, commonly referred as the “optical window”, was observed between 600 and 1350 nm.

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Section: Introductionmentioning

confidence: 99%

The optical properties of mouse skin in the visible and near infrared spectral regions

Sabino

Deana

Yoshimura

et al. 2016

Journal of Photochemistry and Photobiology B: Biology

113

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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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“…4-Pyrazolinyl-1,8-naphthalimide group in the studied compounds was found to easily undergo photooxidation yielding highly emissive 4-pyrazolyl-1,8naphthalimide derivatives. Recently, we have prepared conjugates of propargyl-15 2 ,17 3 -dimethoxy-13 1 -amide of bacteriochlorin e (BChl, Scheme 1) and N-aminobacteriopurpurinimide with 1,8-naphthalimide derivatives [13,14]. This type of fluorescent dyes exhibited high Stockes shifts, good photostability and imaging capability in vitro [14][15][16].…”

mentioning

confidence: 99%

Effect of linker length on the spectroscopic properties of bacteriochlorin – 1,8-naphthalimide conjugates for fluorescence-guided photodynamic therapy

Panchenko

Zakharko

Grin

et al. 2020

Journal of Photochemistry and Photobiology A: Chemistry

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Conjugation of 4-pyrazolinyl-1,8-naphthalimide and propargyl-15 2 ,17 3 -dimethoxy-13 1 -amide of bacteriochlorin e by the oligo(ethylene glycol) linker resulted in the dual function system comprising the modalities of a photosensitizer and a fluorescence imaging agent. In comparison with the conjugate of the same structure but containing the shorter linker, the system demonstrated the higher emission intensity originating from the naphthalimide unit, which could be explained by the decrease in resonance energy transfer efficiency between the chromophores. It has been shown that the ability of bacteriochlorin to generate singlet oxygen remains at the same level when this fragment is introduced in the conjugate structure. 4-Pyrazolinyl-1,8-naphthalimide group in the studied compounds was found to easily undergo photooxidation yielding highly emissive 4-pyrazolyl-1,8naphthalimide derivatives. Recently, we have prepared conjugates of propargyl-15 2 ,17 3 -dimethoxy-13 1 -amide of bacteriochlorin e (BChl, Scheme 1) and N-aminobacteriopurpurinimide with 1,8-naphthalimide derivatives [13,14]. This type of fluorescent dyes exhibited high Stockes shifts, good photostability and imaging capability in vitro [14][15][16]. However, the fluorescence of naphthalimide core in the studied conjugates was found

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Spectroscopical study of bacteriopurpurinimide–naphthalimide conjugates for fluorescent diagnostics and photodynamic therapy

Cited by 21 publications

References 31 publications

The optical properties of mouse skin in the visible and near infrared spectral regions

The optical properties of mouse skin in the visible and near infrared spectral regions

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

Effect of linker length on the spectroscopic properties of bacteriochlorin – 1,8-naphthalimide conjugates for fluorescence-guided photodynamic therapy

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