Rational design of an “all-in-one” phototheranostic

Yang, Zi‐Shu; Yao, Yuhang; Sedgwick, Adam; Li, Cuicui; Xia, Ye; Wang, Yan; Liu, Kang; Su, Hongmei; Wang, Bing‐Wu; Gao, Song; Sessler, Jonathan L.; Zhang, Junlong

doi:10.1039/d0sc03368e

Cited by 45 publications

(28 citation statements)

References 61 publications

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“…Other porpholactones found uses as chlorophyll models [ 14 ] or as bioinorganic models for intermediates in the catalytic cycles of heme-based peroxidases, catalases, and oxidases [ 3 ]. Porpholactones are better lanthanide sensitizers than porphyrins [ 21 ] and served as bioimaging [ 21 ] or phototheranostic agents [ 30 ], oxygen-sensing dyes in pressure-sensitive paints [ 31 , 32 , 33 ], optical cyanide sensors [ 7 , 34 ], or high-pH sensors [ 35 , 36 ], including as ratiometric dye suitable for the full-field optical mapping of the pH of concrete surfaces [ 36 ]. T F PL-based photosensitizers also exhibit higher lipoprotein binding affinity, cellular uptake, and intracellular localization selectivity when compared to the parent porphyrins [ 37 ].…”

Section: Introductionmentioning

confidence: 99%

Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

2020

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meso-Phenyl- and meso-pentafluorophenyl-porpholactones, their metal complexes, as well as porphyrinoids directly derived from them are useful in a number of technical and biomedical applications, and more uses are expected to be discovered. About a dozen competing and complementary pathways toward their synthesis were reported. The suitability of the methods changes with the meso-aryl group and whether the free base or metal derivatives are sought. These circumstances make it hard for anyone outside of the field of synthetic porphyrin chemistry to ascertain which pathway is the best to produce which specific derivative. We report here on what we experimentally evaluated to be the most efficient pathways to generate the six key compounds from the commercially available porphyrins, meso-tetraphenylporphyrin (TPP) and meso-tetrakis(pentafluorophenyl)porphyrin (TFPP): free base meso-tetraphenylporpholactone (TPL) and meso-tetrakis(pentafluorophenyl)porpholactone (TFPL), and their platinum(II) and zinc(II) complexes TPLPt, TFPLPt, TPLZn, and TFPLZn, respectively. Detailed procedures are provided to make these intriguing molecules more readily available for their further study.

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Section: Introductionmentioning

confidence: 99%

Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

2020

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“…These activatable theranostic agents are endowed with a lower limit of detection, real-time detection of biomarkers, lower toxicity to the normal tissues, higher drug bioavailability and higher SNR 34 . In recent years, optical-based phototheranostics have gained increasing attention, due to the advantages of minimal invasiveness, local treatment and spatio-temporal delivery of light reducing the collateral damage to normal surrounding tissues 35 .…”

Section: Theranostics: ''Multifunctional Agents'' For Image-guided Photodynamic Therapymentioning

confidence: 99%

Recent Advances in Photosensitizers as Multifunctional Theranostic Agents for Imaging-Guided Photodynamic Therapy of Cancer

2021

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In recent years tremendous effort has been invested in the field of cancer diagnosis and treatment with an overall goal of improving cancer management, therapeutic outcome, patient survival, and quality of life. Photodynamic Therapy (PDT), which works on the principle of light-induced activation of photosensitizers (PS) leading to Reactive Oxygen Species (ROS) mediated cancer cell killing has received increased attention as a promising alternative to overcome several limitations of conventional cancer therapies. Compared to conventional therapies, PDT offers the advantages of selectivity, minimal invasiveness, localized treatment, and spatio-temporal control which minimizes the overall therapeutic side effects and can be repeated as needed without interfering with other treatments and inducing treatment resistance. Overall PDT efficacy requires proper planning of various parameters like localization and concentration of PS at the tumor site, light dose, oxygen concentration and heterogeneity of the tumor microenvironment, which can be achieved with advanced imaging techniques. Consequently, there has been tremendous interest in the rationale design of PS formulations to exploit their theranostic potential to unleash the imperative contribution of medical imaging in the context of successful PDT outcomes. Further, recent advances in PS formulations as activatable phototheranostic agents have shown promising potential for finely controlled imaging-guided PDT due to their propensity to specifically turning on diagnostic signals simultaneously with photodynamic effects in response to the tumor-specific stimuli. In this review, we have summarized the recent progress in the development of PS-based multifunctional theranostic agents for biomedical applications in multimodal imaging combined with PDT. We also present the role of different imaging modalities; magnetic resonance, optical, nuclear, acoustic, and photoacoustic in improving the pre-and post-PDT effects. We anticipate that the information presented in this review will encourage future development and design of PSs for improved image-guided PDT for cancer treatment.

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“…However, these Ln ions are known to promote the intersystem crossing (ISC) due to the heavy atom effect of Lu and Gd with large spin‐orbit coupling constants of 1163 cm −1 and 1651 cm −1 , respectively. Our group reported Lu porphyrinoids as photosensitizers in triplet‐triplet annihilation‐upconversion (TTA) [55] and theranostic agents [56] . Importantly, to reduce solvent quenching and improve Φ UC , we encapsulated Lu ‐ 1 and Lu ‐ 2 into mesoporous silica nanoparticles (MSNs) and observed the up‐conversion fluorescence in living cells (Figure 11).…”

Section: Lanthanide Complexes For Bioimaging Therapy and Theranosticsmentioning

confidence: 99%

Porpholactone Chemistry: Shining New Light on an Old Cofactor

2020

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The emergence of porpholactone chemistry, discovered over 30 years ago, has significantly stimulated the development of biomimetic tetrapyrrole chemistry. It offers an opportunity, through modifications of non‐pyrrolic building blocks, to clarify the relationship between chemical structure and excited‐state properties, deciphering the structural code for the biological functions of life pigments. With intriguing photophysical properties in the red to near‐infrared (NIR) regions, facile modulation of their electronic nature by fine‐tuning chemical structures, and coordination ability with diverse metal ions, these novel porphyrinoids have favorable prospects in the fields of optical materials, bioimaging and therapy, and catalysis. In this Minireview, we summarize the brief history of porpholactone chemistry, and focus on the studies carried out in our group, particularly on the regioisomeric effect, NIR lanthanide luminescence, and metal catalysis. We outline the perspectives of these compounds in the construction of porpholactone‐related biomedical applications and optical and energy materials, in order to inspire more interest and further advance bioinspired inorganic chemistry and lanthanide chemical biology.

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Rational design of an “all-in-one” phototheranostic

Abstract: Phototheranostics integrate both optical-based imaging modalities and light-based therapies into one single molecular entity. In principle, this strategy could enhance the precision of disease diagnosis and treatment through the simultaneous...

Cited by 45 publications

References 61 publications

Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

Recent Advances in Photosensitizers as Multifunctional Theranostic Agents for Imaging-Guided Photodynamic Therapy of Cancer

Porpholactone Chemistry: Shining New Light on an Old Cofactor

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