21,23-Dithia-3,13-diazaporphycenes − Novel Aromatic Porphycene Analogues Incorporating Thiazole

Nußbaumer, Thomas; Krieger, Claus; Neidlein, R.

doi:10.1002/1099-0690(200007)2000:13<2449::aid-ejoc2449>3.3.co;2-6

Cited by 12 publications

(23 citation statements)

References 3 publications

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“…Extension of the porphycene core, as in 22π and 26π acetylene-cumulene porphycenes, also shows a clear red-shift pattern, consistent with the increased size of the conjugation pathway from 18 to 22 and 26 π electrons, respectively [78,179]. Finally, red shifts can also be induced by introduction of heteroatoms in the porphycene core [92,110,[115][116][117][118][119][120].…”

Section: Absorption Spectramentioning

confidence: 55%

“…Finally, red shifts can also be induced by introduction of heteroatoms in the porphycene core [92,110,[115][116][117][118][119][120]. The batho-and hyperchromic effects brought about by aza substitution in porphyrins encouraged exploration of whether such effects would also occur in porphycenes.…”

Section: The Ideal Pdt Sensitizermentioning

confidence: 99%

“…Decades of research on porphyrins have provided clues for the design of PSs approaching the ideal above: red shifts in the absorption spectrum (bathochromism) can be achieved by enlarging the size of the aromatic macrocycle thus destabilizing the highest occupied molecular orbital (HOMO) [77][78][79][80][81][82][83][84], by suitable peripheral functionalization [71,83,85,86], or by introducing heteroatoms in the macrocycle core, particularly nitrogens [79,83,[87][88][89][90][91][92][93][94].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Stockert¹,

Cañete²,

Juarranz³

et al. 2007

CMC

177

130

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The photodynamic process induces cell damage and death by the combined effect of a photosensitizer (PS), visible light, and molecular oxygen, which generate singlet oxygen ((1)O(2)) and other reactive oxygen species that are responsible for cytotoxicity. The most important application of this process with increasing biomedical interest is the photodynamic therapy (PDT) of cancer. In addition to hematoporphyrin-based drugs, 2nd generation PSs with better photochemical properties are now studied using cell cultures, experimental tumors and clinical trials. Porphycene is a structural isomer of porphyrin and constitutes an interesting new class of PS. Porphycene derivatives show higher absorption than porphyrins in the red spectral region (lambda > 600 nm, epsilon > 50000 M-(1)cm(-1)) owing to the lower molecular symmetry. Photophysical and photobiological properties of porphycenes make them excellent candidates as PSs, showing fast uptake and diverse subcellular localizations (mainly membranous organelles). Several tetraalkylporphycenes and the tetraphenyl derivative (TPPo) induce photodamage and cell death in vitro. Photodynamic treatments of cultured tumor cells with TPPo and its palladium(II) complex induce cytoskeletal changes, mitotic blockage, and dose-dependent apoptotic or necrotic cell death. Some pharmacokinetic and phototherapeutic studies on experimental tumors after intravenous or topical application of lipophilic alkyl-substituted porphycene derivatives are known. Taking into account all these features, porphycene PSs should be very useful for PDT of cancer and other biomedical applications.

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Section: Absorption Spectramentioning

confidence: 55%

Section: The Ideal Pdt Sensitizermentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Porphycenes: Facts and Prospects in Photodynamic Therapy of Cancer

Stockert¹,

Cañete²,

Juarranz³

et al. 2007

CMC

177

130

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“…More recently, novel aromatic porphycene analogues containing thiazole rings have been obtained by oxidation of 143, which was itself prepared by a tandem reaction of the corresponding dicarbaldehydes [186] (Figure 6.25). The spectroscopic properties of the thiazole-derived annulene 144 are similar to those of 143 and do not reflect the typical paratropic behavior of the planar annulene structures of the porphycenes [187].…”

Section: Tandem Coupling Reactionsmentioning

confidence: 99%

The McMurry Coupling and Related Reactions

Ephritikhine

Villiers

2003

Modern Carbonyl Olefination

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“…The majority of thiazolylpyrroles was obtained by Hantzsch reaction from various thioamides of pyrrole series [1,3,4,9,10,1315]. More seldom the pyrrole ring was built up from an acyclic precursor possessing a thiazole substituent [58, 11,1619].…”

mentioning

confidence: 99%