Porphyrins: Electronic Structure and Ultraviolet/Visible Absorption Spectroscopy

Simpson, M. Cather; Novikova, Nina I.

doi:10.1002/9781119129301.ch11

Cited by 5 publications

(10 citation statements)

References 279 publications

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“…In the spectral range 400-407 nm, the Soret band was highlighted as a result of an intense absorption, and the Q bands were identified in the spectral region of 495-629 nm. The presence of the absorption maximum associated with the band Qx(0,0) at 621-630 nm confirmed the fact that the investigated porphyrin compounds absorbed in the phototherapeutic range [19,20].…”

Section: Resultssupporting

confidence: 71%

“…A major advantage of porphyrins is their selectivity for tumor cells and, in contrast to ALA, they do not need metabolization for becoming PS, their tetrapyrrolic structure is stable, and they have good photodynamic properties for PDT [16]. Through their structural profile and electronic load, porphyrins can efficiently generate reactive oxygen species (ROS), such as singlet oxygen, in the presence of molecular oxygen and light [5,6,[17][18][19][20]. A series of pharmaceutical products containing porphyrin-type photosensitizers (e.g., Metvix ® , Levulan ® , Photogem ® , Purlytin ® , Foscan ® , Foslip ® ), are presently used for various skin disorders.…”

Section: Introductionmentioning

confidence: 99%

“…Porphyrins were further investigated in vitro on human skinrelevant cell lines, either normal (HaCaT keratinocytes and Hs27 fibroblasts) or tumoral (SCL II squamous cell carcinoma), as well as on mouse B16F10 melanoma cells. The particular spectral characteristics associated with porphyrinic structures recommend this structural type in PDT applied to malignant diseases [1,5,[17][18][19][20]33]. The molecular absorption spectrum of a porphyrin is described by five spectral bands: an intense band (Soret band) in the 390-440 nm spectral range and four other Q bands located in the 440-700 nm spectral range [34][35][36].…”

Section: Introductionmentioning

confidence: 99%

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Assessment of Some Unsymmetrical Porphyrins as Promising Molecules for Photodynamic Therapy of Cutaneous Disorders

Burloiu,

Manda,

Lupuliasa

et al. 2023

Pharmaceuticals

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In order to select for further development novel photosensitizers for photodynamic therapy in cutaneous disorders, three unsymmetrical porphyrins, namely 5-(4-hydroxy-3-methoxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl) porphyrin (P2.2), 5-(2-hydroxy-5-methoxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl) porphyrin (P3.2), and 5-(2,4-dihydroxyphenyl)-10,15,20-tris-(4-acetoxy-3-methoxyphenyl) porphyrin (P4.2), along with their fully symmetrical counterparts 5,10,15,20-tetrakis-(4-acetoxy-3-methoxyphenyl) porphyrin (P2.1) and 5,10,15,20-tetrakis-(4-carboxymethylphenyl) porphyrin (P3.1) were comparatively evaluated. The absorption and fluorescence properties, as well as atomic force microscopy measurements were performed to evaluate the photophysical characteristics as well as morphological and textural properties of the mentioned porphyrins. The cellular uptake of compounds and the effect of photodynamic therapy on the viability, proliferation, and necrosis of human HaCaT keratinocytes, human Hs27 skin fibroblasts, human skin SCL II squamous cell carcinoma, and B16F10 melanoma cells were assessed in vitro, in correlation with the structural and photophysical properties of the investigated porphyrins, and with the predictions regarding diffusion through cell membranes and ADMET properties. All samples were found to be isotropic and self-similar, with slightly different degrees of aggregability, had a relatively low predicted toxicity (class V), and a predicted long half-life after systemic administration. The in vitro study performed on non-malignant and malignant skin-relevant cells highlighted that the asymmetric P2.2 porphyrin qualified among the five investigated porphyrins to be a promising photosensitizer candidate for PDT in skin disorders. P2.2 was shown to accumulate well within cells, and induced by PDT a massive decrease in the number of metabolically active skin cells, partly due to cell death by necrosis. P2.2 had in this respect a better behavior than the symmetric P.2.1 compound and the related asymmetric compound P4.2. The strong action of P2.2-mediated PDT on normal skin cells might be an important drawback for further development of this compound. Meanwhile, the P3.1 and P3.2 compounds were not able to accumulate well in skin cells, and did not elicit significant PDT in vitro. Taken together, our experiments suggest that P2.2 can be a promising candidate for the development of novel photosensitizers for PDT in skin disorders.

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Section: Resultssupporting

confidence: 71%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Assessment of Some Unsymmetrical Porphyrins as Promising Molecules for Photodynamic Therapy of Cutaneous Disorders

Burloiu,

Manda,

Lupuliasa

et al. 2023

Pharmaceuticals

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“…Porphyrins are available macroheterocyclic compounds which play an important role in diverse areas of scientific research owing to their unique photophysical, electrochemical, and optical properties [ 1 ]. They have been widely studied in biomedical applications, as biosensors, bioimaging probes, and especially as photosensitizers (PSs) in photodynamic therapy (PDT) [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

Alpatova,

Rys,

Kononova

et al. 2024

Beilstein J. Org. Chem.

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A carboranylporphyrin of A3B-type bearing a single pentafluorophenyl ring was prepared through the regioselective nucleophilic aromatic substitution reaction of the p-fluorine atoms in 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin with 9-mercapto-m-carborane. The reaction of this porphyrin with sodium azide led to the selective substitution of the p-fluorine atom in the pentafluorophenyl substituent with an azide functionality which upon reduction with SnCl2 resulted in the formation of the corresponding porphyrin with an amino group. Pentafluorophenyl-substituted A3B-porphyrins were studied and transformed to thiol and amino-substituted compounds allowing for the preparation of porphyrins with different reactive groups such as hydroxy and amino derivatives capable for further functionalization and conjugation of these porphyrins to other substrates. In addition, conjugates containing maleimide or biotin entities in the structure of carborane A3B-porphyrin were also synthesized based on the amino-substituted A3B-porphyrin. The structures of the prepared carboranylporphyrins were determined by UV–vis, IR, 1H, 19F, 11B NMR spectroscopic data and MALDI mass spectrometry.

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“…Porphyrins possess selectivity for tumor cells, low cytotoxicity in the absence of light, and peculiar photophysical properties (absorption and emission in the visible region, high triplet state quantum yield, high quantum yield of 1 O 2 * generation), which have drawn research interest for their use as theranostic agents [ 8 , 9 , 10 , 11 , 12 , 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Porphyrin Macrocycles: General Properties and Theranostic Potential

et al. 2023

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Despite specialists’ efforts to find the best solutions for cancer diagnosis and therapy, this pathology remains the biggest health threat in the world. Global statistics concerning deaths associated with cancer are alarming; therefore, it is necessary to intensify interdisciplinary research in order to identify efficient strategies for cancer diagnosis and therapy, by using new molecules with optimal therapeutic potential and minimal adverse effects. This review focuses on studies of porphyrin macrocycles with regard to their structural and spectral profiles relevant to their applicability in efficient cancer diagnosis and therapy. Furthermore, we present a critical overview of the main commercial formulations, followed by short descriptions of some strategies approached in the development of third-generation photosensitizers.

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Porphyrins: Electronic Structure and Ultraviolet/Visible Absorption Spectroscopy

Cited by 5 publications

References 279 publications

Assessment of Some Unsymmetrical Porphyrins as Promising Molecules for Photodynamic Therapy of Cutaneous Disorders

Assessment of Some Unsymmetrical Porphyrins as Promising Molecules for Photodynamic Therapy of Cutaneous Disorders

Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

Porphyrin Macrocycles: General Properties and Theranostic Potential

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Porphyrins: Electronic Structure and Ultraviolet/Visible Absorption Spectroscopy

Cited by 5 publications

References 279 publications

Assessment of Some Unsymmetrical Porphyrins as Promising Molecules for Photodynamic Therapy of Cutaneous Disorders

Assessment of Some Unsymmetrical Porphyrins as Promising Molecules for Photodynamic Therapy of Cutaneous Disorders

Synthesis of new representatives of A3B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

Porphyrin Macrocycles: General Properties and Theranostic Potential

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Product

Resources

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Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations