The evaluation of NIR-absorbing porphyrin derivatives as contrast agents in photoacoustic imaging

Abuteen, Akram; Zanganeh, Saeid; Akhigbe, Joshua; Samankumara, Lalith P.; Aguirre, Andres; Biswal, Nrusingh C.; Braune, Marcel; Vollertsen, Anke R.; Röder, Beate; Brückner, Christian; Zhu, Quing

doi:10.1039/c3cp52193a

Cited by 76 publications

(52 citation statements)

References 64 publications

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“…However, their very low fluorescence and singlet oxygen quantum yields, reported earlier, 9 prevent their use as PDT agents, but we were able to show that this class of porphyrinoids is suitable as contrast agents for photoacoustic imaging applications. 9 We are currently in the process of preparing a range of quinoline-annulated porphyrins that possess more favorable solubility properties for their use in aqueous biological environments.…”

Section: Resultsmentioning

confidence: 99%

“…Non-emitting chromophores may also be attractive as photoacoustic imaging agents but, 8 again, only if they also absorb light within the optical window of tissue. 9 Light-harvesting applications also benefit from NIR-absorbing dyes as a large portion of the irradiance energy of sunlight falls into this range. Panchromatic absorbers are also most desirable for light harvesting as these chromophores collect the maximum amount of energy.…”

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confidence: 99%

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Mono- and Bisquinoline-Annulated Porphyrins from Porphyrin β,β′-Dione Oximes

et al. 2014

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An acid-induced reaction of meso-tetraphenyl-2-hydroxyimino-3-oxoporphyrin leads, with concomitant loss of water, to a formal electrophilic aromatic substitution of the ortho-position of the phenyl group adjacent to the oxime, forming a quinoline moiety. Owing in part to the presence of a π-extended chromophore, the resulting meso-triphenylmonoquinoline-annulated porphyrin (λmax = 750 nm) possesses a much altered optical spectrum from that of the starting oxime (λmax = 667 nm). An oxidative DDQ-induced ring-closure process is also possible, generating the corresponding meso-triphenylmonoquinoline-annulated porphyrin quinoline N-oxide, possessing a slightly shifted and sharpened UV-vis spectrum (λmax = 737 nm). The connectivity of the chromophores was conclusively shown by NMR spectroscopy. Both ketone functionalities in meso-tetraphenyl-2,3-dioxoporphyrin can be converted, via the oxime and using the acid- or oxidant-induced reaction pathways, either in one step or in a stepwise fashion, to bisquinoline-annulated porphyrin (λmax = 775 nm) and its N-oxide (λmax = 779 nm), respectively. This process is complementary to a previously established pathway toward bisquinoline-annulated porphyrins. Their zinc(II), nickel(II), and palladium(II) complexes are also described. Several examples of the quinoline-annulated porphyrins were crystallographically characterized, proving their connectivity and showing their conformations that are extremely distorted from planarity. The work presents a full account on the synthesis, structure, and spectroscopic properties of these classes of NIR-absorbing dyes.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Mono- and Bisquinoline-Annulated Porphyrins from Porphyrin β,β′-Dione Oximes

et al. 2014

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“…17 We demonstrated a ~ 2.5-fold PAI contrast enhancement for 4a over pure blood or ICG in phantom tissue experiments. The realization of the combination of a NIR-absorbing chromophores showing good photoacoustic signal generation efficiency is difficult, as the direct comparison of a number of NIR dyes absorbing in the same wavelength range has shown.…”

Section: Introductionmentioning

confidence: 71%

“…Thus, PEGylated quinoline-annulated porphyrin 4e , like its parent compound, 17 absorbs strongly within the spectroscopic window of tissue, is non-emissive, and not generating 1 O 2 . These are excellent properties for a photoacoustic imaging agent.…”

Section: Resultsmentioning

confidence: 97%

“…The realization of the combination of a NIR-absorbing chromophores showing good photoacoustic signal generation efficiency is difficult, as the direct comparison of a number of NIR dyes absorbing in the same wavelength range has shown. 17 Despite the promise of 4a or 5a as PAI contrast agents, however, their insolubility in aqueous solutions (in the absence of a formulation vehicle like Cremophore EL®) prevented their in vivo assessment.…”

Section: Introductionmentioning

confidence: 99%

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In vivo photoacoustic tumor tomography using a quinoline-annulated porphyrin as NIR molecular contrast agent

et al. 2017

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The synthesis and photophysical properties of a tetra-PEG-modified and freely water-soluble quinoline-annulated porphyrin are described. We previously demonstrated the ability of quinoline-annulated porphyrins to act as an in vitro NIR photoacoustic imaging (PAI) contrast agent. The solubility of the quinoline-annulated porphyrin derivative in serum now allowed the assessment of the efficacy of the PEGylated derivative as an in vivo NIR contrast agent for the PAI of an implanted tumor in a mouse model. A multi-fold contrast enhancement when compared to the benchmark dye ICG could be shown, a finding that could be traced to its photophysical properties (short triplet lifetimes, low fluorescence and singlet oxygen sensitization quantum yields). A NIR excitation wavelength of 790 nm could be used, fully taking advantage of the optical window of tissue. Rapid renal clearance of the dye was observed. Its straight-forward synthesis, optical properties with the possibility for further optical fine-tuning, nontoxicity, favorable elimination rates, and contrast enhancement make this a promising PAI contrast agent. The ability to conjugate the PAI chromophore with a fluorescent tag using a facile and general conjugation strategy was also demonstrated.

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Single Molecule with Dual Function on Nanogold: Biofunctionalized Construct for In Vivo Photoacoustic Imaging and SERS Biosensing

Dinish

Song

et al. 2015

Adv Funct Materials

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Multimodal imaging provides complimentary information that is advantageous in studying both cellular and molecular mechanisms in vivo, which has tremendous potential in pre-clinical research and clinical translational imaging. It is desirable to design probes for multimodal imaging that can be administered minimally but provides multifaceted information. Herein, we demonstrate the complementary dual functional ability of a nanoconstruct for molecular imaging in both photoacoustic (PA) and surface-enhanced Raman scattering (SERS) biosensing simultaneously in tandem. To realize this, a group of NIR active organic molecules are designed and synthesized that possess both SERS and PA activity. Nanoconstructs realized by anchoring such molecules onto gold nanoparticles are demonstrated for targeting cancer biomarkers in vivo while providing complimentary information about biodistribution and targeting effi ciency. In future, such nanoconstructs could play a major role in identifying surgical margins and also for disease monitoring in translational medicine.

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The evaluation of NIR-absorbing porphyrin derivatives as contrast agents in photoacoustic imaging

Cited by 76 publications

References 64 publications

Mono- and Bisquinoline-Annulated Porphyrins from Porphyrin β,β′-Dione Oximes

Mono- and Bisquinoline-Annulated Porphyrins from Porphyrin β,β′-Dione Oximes

In vivo photoacoustic tumor tomography using a quinoline-annulated porphyrin as NIR molecular contrast agent

Single Molecule with Dual Function on Nanogold: Biofunctionalized Construct for In Vivo Photoacoustic Imaging and SERS Biosensing

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