Supramolecular Photonic Therapeutic Agents

McDonnell, Susan; Hall, Michael J.; Allen, Lorcan T.; Byrne, Annette T.; Gallagher, William M.; O’Shea, Donal F.

doi:10.1021/ja0553497

Cited by 331 publications

(272 citation statements)

References 12 publications

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“…Unlike many other PDT photosensitisers, ADPM agents are synthetic and can be readily modified about the core periphery to affect drug properties (McDonnell et al, 2005). In this study, we have shown our lead agent, ADPM06, to be well tolerated and highly efficacious in vivo, when a short drug -light interval protocol was used.…”

Section: Discussionmentioning

confidence: 86%

Vascular-targeted photodynamic therapy with BF2-chelated Tetraaryl-Azadipyrromethene agents: a multi-modality molecular imaging approach to therapeutic assessment

et al. 2009

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BACKGROUND: Photodynamic therapy (PDT) is a treatment modality for a range of diseases including cancer. The BF 2 -chelated tetraaryl-azadipyrromethenes (ADPMs) are an emerging class of non-porphyrin PDT agent, which have previously shown excellent photochemical and photophysical properties for therapeutic application. Herein, in vivo efficacy and mechanism of action studies have been completed for the lead agent, ADMP06. METHODS: A multi-modality imaging approach was employed to assess efficacy of treatment, as well as probe the mechanism of action of ADPM06-mediated PDT. RESULTS: Tumour ablation in 71% of animals bearing mammary tumours was achieved after delivery of 2 mg kg À1 of ADPM06 followed immediately by light irradiation with 150 J cm À2 . The inherent fluorescence of ADPM06 was utilised to monitor organ biodistribution patterns, with fluorescence reaching baseline levels in all organs within 24 h. Mechanism of action studies were carried out using dynamic positron emission tomography and magnetic resonance imaging techniques, which, when taken together, indicated a decrease in tumour vascular perfusion and concomitant reduction in tumour metabolism over time after treatment. CONCLUSION: The encouraging treatment responses in vivo and vascular-targeting mechanism of action continue to indicate therapeutic benefit for this new class of photosensitiser.

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Section: Discussionmentioning

confidence: 86%

Vascular-targeted photodynamic therapy with BF2-chelated Tetraaryl-Azadipyrromethene agents: a multi-modality molecular imaging approach to therapeutic assessment

et al. 2009

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“…Owing to their advantageous and tunable photophysical properties and ability to generate singlet oxygen ( 1 O 2 )c oupled with absorption of light from the socalled "therapeuticw indow"( 600 nm-1100 nm), aza-BODIPY dyes have been proposed as potential triplet photosensitizers for both anti-microbiala nd anti-cancer photodynamic therapy. [20,[30][31][32][33][34][35][36][37][38][39][40][41] Aza-BODIPYs continue to attracta ttention as chemosensors for the detection of ammonia, [42] cysteine, homocysteine and glutathione in living cells, [43] Hg 2 + , [44][45][46] F À , [47,48] in vivo detection of H 2 S, [49] carbon dioxide, [50] glucosei nw hole blood, [51] detection of saxitoxin [52] and pH-sensitive sensors. [52] Furthermore, aza-BODIPYs have been proposed as photoactive components in photovoltaic devices [54][55][56] and nonlinear optical materials.…”

Section: Introductionmentioning

confidence: 99%

Visible‐Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza‐BODIPYs: Synthesis, Photophysics and Redox Properties

Gut

Łapok

Drelinkiewicz

et al. 2017

Chemistry An Asian Journal

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As eries of novel iodinated NO 2 -substituted azaBODIPYs have been synthesized and characterized.H ighly desirable photophysical and photochemical properties were induced in NO 2 -substituted aza-BODIPYs by iodinationo ft he pyrrole rings. In particular, highv alues of singlet oxygen quantum yields (F D )r anging from 0.79 to 0.85 were measured. The photooxygenation process proceeds via aT ype II mechanism under the experimental conditions applied. The compounds studied exhibited an absorption band within the so-called "therapeutic window", with l max located between 645 nm to 672 nm. They were non-fluorescent at room temperature with excited singlet-state lifetimes within the picosecond range as measured by femtosecond transient absorption. Nanosecond laser flash photolysis experiments revealed T 1 !T n absorption spanning from ca. 400 nm to ca. 500 nm and allowedd etermination of the triplet-state lifetimes. The estimated triplet lifetimes (t T )i nd eaerated acetonitrile ranged between 2.74 msa nd 3.50 ms. As estimated by CV/DPV measurements, all iodinateda za-BODIPYs studied exhibited one irreversible oxidation and two quasireversible reductions processes. Estimation of the E HOMO gave the value of À6.06 to À6.26 eV while the E LUMO was found to be located at ca. À4.6 eV.T hermogravimetric (TGA) analysis revealed that iodinated aza-BODIPYs weres table up to approximately 300 8C. All compounds studied exhibit high photostability in toluene solution.

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“…Another approach is based on photoinduced electron transfer (PET) from amines to aromatic system of the chromophore that quenches the excited states. [3,6,7] The wavelength of excitation and emission of the dyes employed in these applications are optimally over 640 nm, because of deeper penetration of the light through tissues and the elimination of possible autofluorescence of the endogenous chromophores, for example hemoglobin. [1] Phthalocyanines (Pc) and their aza analogues, azaphthalocyanines (AzaPc), are characterized by strong absorptions, which are usually over 650 nm, good chemical stability, low photobleaching, and sufficient quantum yields of fluorescence (F F ) and singlet oxygen (F D ).…”

Section: Introductionmentioning

confidence: 99%

Red‐Emitting Dyes with Photophysical and Photochemical Properties Controlled by pH

Novakova

Miletín

Kopecký

et al. 2011

Chemistry A European J

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New unsymmetrical zinc azaphthalocyanines, bearing one substituted aniline as a peripheral substituent, were prepared by using a statistical condensation approach. Both fluorescence and singlet oxygen quantum yields were extremely low in DMF (Φ(F)<0.01, Φ(Δ)<0.02, respectively), but increased after the addition of sulfuric acid, reaching values comparable to controls without aniline substituents (Φ(F)=0.22-0.29, Φ(Δ)=0.40-0.59, respectively). This behavior was attributed to the deactivation of excited states by intramolecular charge transfer from a donor site (aniline), which was blocked after protonation in acidic media. In the protonated form, all of the compounds efficiently emitted light with λ(em) in the region of 662-675 nm. The investigated compounds were anchored to dioleoylphosphatidylcholine (DOPC) unilamellar vesicles and showed response to buffer pH. They were highly fluorescent at low pH values and almost nonfluorescent in neutral solutions. The pK(a) values were determined in DOPC vesicles and ranged between 2.2 and 4.2.

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Supramolecular Photonic Therapeutic Agents

Cited by 331 publications

References 12 publications

Vascular-targeted photodynamic therapy with BF2-chelated Tetraaryl-Azadipyrromethene agents: a multi-modality molecular imaging approach to therapeutic assessment

Vascular-targeted photodynamic therapy with BF2-chelated Tetraaryl-Azadipyrromethene agents: a multi-modality molecular imaging approach to therapeutic assessment

Visible‐Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza‐BODIPYs: Synthesis, Photophysics and Redox Properties

Red‐Emitting Dyes with Photophysical and Photochemical Properties Controlled by pH

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