Fluorinated photosensitizers: synthesis, photophysical, electrochemical, intracellular localization, in vitro photosensitizing efficacy and determination of tumor-uptake by 19F in vivo NMR spectroscopy

Pandey, Suresh K; Gryshuk, Amy; Graham, Andrew E.; Ohkubo, Kei; Fukuzumi, Shunichi; Dobhal, M. P.; Zheng, Gang; Ou, Zhongping; Zhan, Riqiang; Kadish, Karl M.; Oseroff, Allan R.; Ramaprasad, S.; Pandey, Ravindra K.

doi:10.1016/j.tet.2003.10.016

Cited by 59 publications

(25 citation statements)

References 23 publications

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“…Under our experimental conditions, no phosphorescence emission could be detected unambiguously from our molecules, as is generally the case for free-base porphyrins and related macrocycles. [28] Reports of phosphorescence from free-base bacteriochlorins must be regarded with caution, [29] as we also have been misled by the phosphorescence of impurities in free-base chlorin samples. [21,30] An alternative approach to measuring the triplet-state energies of these molecules is to use photoacoustic calorimetry (PAC).…”

Section: Resultsmentioning

confidence: 99%

Mechanisms of Singlet‐Oxygen and Superoxide‐Ion Generation by Porphyrins and Bacteriochlorins and their Implications in Photodynamic Therapy

Silva

Serpa

Dąbrowski

et al. 2010

Chemistry A European J

166

127

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New halogenated and sulfonated bacteriochlorins and their analogous porphyrins are employed as photosensitizers of singlet oxygen and the superoxide ion. The mechanisms of energy and electron transfer are clarified and the rates are measured. The intermediacy of a charge-transfer (CT) complex is proved for bacteriochlorins, but excluded for porphyrins. The energies of the intermediates and the rates of their interconversions are measured, and are used to obtain the efficiencies of all the processes. The mechanism of formation of the hydroxyl radical in the presence of bacteriochlorins is proposed to involve a photocatalytic step. The usefulness of these photosensitizers in the photodynamic therapy (PDT) of cancer is assessed, and the following recommendations are given for the design of more effective PDT protocols employing such photosensitizers: 1) light doses should be given over a more extended period of time when the photosensitizers form CT complexes with molecular oxygen, and 2) Fe(2+) may improve the efficiency of such photosensitizers if co-located in the same cell organelle assisting with an in vivo Fenton reaction.

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Section: Resultsmentioning

confidence: 99%

Mechanisms of Singlet‐Oxygen and Superoxide‐Ion Generation by Porphyrins and Bacteriochlorins and their Implications in Photodynamic Therapy

Silva

Serpa

Dąbrowski

et al. 2010

Chemistry A European J

166

127

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“…This can be very useful for diagnosis and adds to the well-known use of fluorinated compounds as probes in magnetic resonance imaging. [41][42][43] …”

Section: -Octanol/water Partition Coefficientsmentioning

confidence: 99%

Synthesis of amphiphilic sulfonamide halogenated porphyrins: MALDI-TOFMS characterization and evaluation of 1-octanol/water partition coefficients

et al. 2008

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a b s t r a c tPorphyrins are key precursors for development of photosensitizers for photodynamic therapy. A new series of ortho-halogenated tetraarylporphyrins with sulfonamide substituents have been synthesized via chlorosulfonation reaction and characterized by MALDI-TOFMS. To predict their partition properties, log K OW of a selected range of the synthesized halogenated amphiphilic porphyrins is described. A significant effect of the number and type of halogen group as well as on the number of sulfonamide side chain was observed. The determined 1-octanol/water partition coefficients showed that it is possible to obtain compounds with a wide range of lipophilicities, from log K OW ¼À2.71 till log K OW >4, which are suitable to optimize the biological efficacy of this class of sensitizers.

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“…Dupont's catalyst proved to be very efficient in the synthesis of non‐symmetric BTD derivatives 2a , 2b , 2c , which could be obtained in good yields (71–75%). The beneficial effect of fluorine for the photophysical properties of fluorescent π‐extended compounds is known . Considering there is a very electron deficient substituent in the phenyl group in derivative 2a (fluorine atom) on one side of the BTD ring, which results in a high polarization of the structure (high dipole moment, as calculated herein), we decided to incorporate on the other side a group with a long alkyl chain (C8) and try to observe a possible liquid crystalline behavior (Scheme ) in a similar strategy already used for symmetrical BTDs .…”

Section: Resultsmentioning

confidence: 99%

Designed non‐symmetrical 4,7‐pi‐extended‐2,1,3‐benzothiadiazole derivatives: Synthesis guided by DFT predictions

Lopes

Filho

Lapis

et al. 2013

J of Physical Organic Chem

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A series of rationally designed, non‐symmetrical, 4,7‐π‐extended‐2,1,3‐benzothidiazole derivatives had their electronic and geometrical properties evaluated by means of DFT calculations. The data obtained from the calculated 2,1,3‐benzothiadiazole (BTD) intermediates allowed the design and synthesis of a final structure bearing a fluorine‐containing aromatic group on one side of the BTD ring and a C≡C spacer linking a long chain‐containing (C8) aromatic group on the other side. This specific molecular architecture is expected to display liquid crystalline behavior. The new designed structure was therefore synthesized in good overall yield using cross‐coupling reactions (Suzuki and Sonogashira reactions). Copyright © 2013 John Wiley & Sons, Ltd.

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Fluorinated photosensitizers: synthesis, photophysical, electrochemical, intracellular localization, in vitro photosensitizing efficacy and determination of tumor-uptake by 19F in vivo NMR spectroscopy

Cited by 59 publications

References 23 publications

Mechanisms of Singlet‐Oxygen and Superoxide‐Ion Generation by Porphyrins and Bacteriochlorins and their Implications in Photodynamic Therapy

Mechanisms of Singlet‐Oxygen and Superoxide‐Ion Generation by Porphyrins and Bacteriochlorins and their Implications in Photodynamic Therapy

Synthesis of amphiphilic sulfonamide halogenated porphyrins: MALDI-TOFMS characterization and evaluation of 1-octanol/water partition coefficients

Designed non‐symmetrical 4,7‐pi‐extended‐2,1,3‐benzothiadiazole derivatives: Synthesis guided by DFT predictions

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