Photophysics of Glycosylated Derivatives of a Chlorin, Isobacteriochlorin and Bacteriochlorin for Photodynamic Theragnostics: Discovery of a Two‐photon‐absorbing Photosensitizer

Aggarwal, Amit; Thompson, Sebastián; Singh, Sunaina; Newton, Brandon; Moore, Akeem; Gao, Ruomie; Gu, Xin-Bin; Mukherjee, Sushmita; Drain, Charles Michael

doi:10.1111/php.12179

Cited by 38 publications

(29 citation statements)

References 81 publications

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“…Here two separate near-infrared photons have to arrive at the PS molecule virtually simultaneously, and if they are absorbed at the same time they will be equivalent to a single photon of half the wavelength [130]. However, the need for simultaneous absorption of both photons means that an extremely high peak power density (in the order of GW/cm 2 ) is required.…”

Section: Future Directionsmentioning

confidence: 99%

New photosensitizers for photodynamic therapy

Abrahamse

Hamblin

2016

Biochemical Journal

1,668

1,172

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Photodynamic therapy (PDT) was discovered more than 100 years ago, and has since become a well-studied therapy for cancer and various non-malignant diseases including infections. PDT uses photosensitizers (PSs, non-toxic dyes) that are activated by absorption of visible light to initially form the excited singlet state, followed by transition to the long-lived excited triplet state. This triplet state can undergo photochemical reactions in the presence of oxygen to form reactive oxygen species (including singlet oxygen) that can destroy cancer cells, pathogenic microbes and unwanted tissue. The dual-specificity of PDT relies on accumulation of the PS in diseased tissue and also on localized light delivery. Tetrapyrrole structures such as porphyrins, chlorins, bacteriochlorins and phthalocyanines with appropriate functionalization have been widely investigated in PDT, and several compounds have received clinical approval. Other molecular structures including the synthetic dyes classes as phenothiazinium, squaraine and BODIPY (boron-dipyrromethene), transition metal complexes, and natural products such as hypericin, riboflavin and curcumin have been investigated. Targeted PDT uses PSs conjugated to antibodies, peptides, proteins and other ligands with specific cellular receptors. Nanotechnology has made a significant contribution to PDT, giving rise to approaches such as nanoparticle delivery, fullerene-based PSs, titania photocatalysis, and the use of upconverting nanoparticles to increase light penetration into tissue. Future directions include photochemical internalization, genetically encoded protein PSs, theranostics, two-photon absorption PDT, and sonodynamic therapy using ultrasound.

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Section: Future Directionsmentioning

confidence: 99%

New photosensitizers for photodynamic therapy

Abrahamse

Hamblin

2016

Biochemical Journal

1,668

1,172

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“…These com-pounds were also studied for two photon fluorescence imaging on Chinese hamster ovary cells and we found that IGlc 4 has good two photon absorption (TPA) between 760 and 880 nm, and the cross section is 24.5 GM at 860 nm. 93 …”

Section: Substituted Fluorinated Porphyrinoids For Biological Applicamentioning

confidence: 99%

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

et al. 2016

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Porphyrinoids are robust heterocyclic dyes studied extensively for their applications in medicine and as photonic materials because of their tunable photophysical properties, diverse means of modifying the periphery, and the ability to chelate most transition metals. Commercial applications include their use as phthalocyanine dyes in optical discs, porphyrins in photodynamic therapy, and as oxygen sensors. Most applications of these dyes require exocyclic moieties to improve solubility, target diseases, modulate photophysical properties, or direct the self-organization into architectures with desired photonic properties. The synthesis of the porphyrinoid depends on the desired application, but the de novo synthesis often involves several steps, is time consuming, and results in low isolated yields. Thus, the application of core porphyrinoid platforms that can be rapidly and efficiently modified to evaluate new molecular architectures allows researchers to focus on the design concepts rather than the synthesis methods, and opens porphyrinoid chemistry to a broader scientific community. We have focused on several widely available, commercially viable porphyrinoids as platforms: meso-perfluorophenylporphyrin, perfluoro-phthalocyanine, and meso-perfluorophenylcorrole. The perfluorophenylporphyrin is readily converted to the chlorin, bacteriochlorin, and isobacteriochlorin. Derivatives of all six of these core platforms can be efficiently and controllably made via mild nucleophilic aromatic substitution reactions using primary S, N, and O nucleophiles bearing a wide variety of functional groups. The remaining fluoro groups enhance the photo and oxidative stability of the dyes and can serve as spectroscopic signatures to characterize the compounds or in imaging applications using 19F NMR. This review provides an overview of the chemistry of fluorinated porphyrinoids that are being used as a platform to create libraries of photo-active compounds for applications in medicine and materials.

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“…Light with λ >850 nm, however, does not provide enough energy for excitation of 3 O 2 to 1 O 2 [100,106]. This drawback is eliminated by simultaneous absorption of two photons by the PS, to provide the same energy as a single photon of shorter wavelength [107]. …”

Section: Photosensitizersmentioning

confidence: 99%

Photodynamic Therapy: Current Status and Future Directions

Benov¹

2014

Med Princ Pract

351

299

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Photodynamic therapy (PDT) is a minimally invasive therapeutic modality used for the management of a variety of cancers and benign diseases. The destruction of unwanted cells and tissues in PDT is achieved by the use of visible or near-infrared radiation to activate a light-absorbing compound (a photosensitizer, PS), which, in the presence of molecular oxygen, leads to the production of singlet oxygen and other reactive oxygen species. These cytotoxic species damage and kill target cells. The development of new PSs with properties optimized for PDT applications is crucial for the improvement of the therapeutic outcome. This review outlines the principles of PDT and discusses the relationship between the structure and physicochemical properties of a PS, its cellular uptake and subcellular localization, and its effect on PDT outcome and efficacy.

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Photophysics of Glycosylated Derivatives of a Chlorin, Isobacteriochlorin and Bacteriochlorin for Photodynamic Theragnostics: Discovery of a Two‐photon‐absorbing Photosensitizer

Cited by 38 publications

References 81 publications

New photosensitizers for photodynamic therapy

New photosensitizers for photodynamic therapy

Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics

Photodynamic Therapy: Current Status and Future Directions

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