Developing a structure–function relationship for anionic porphyrazines exhibiting selective anti-tumor activity

Spectroscopy, Binding to Liposomes and Production of Singlet Oxygen by Porphyrazines with Modularly Variable Water Solubility

“…We show that (1) having metal coordinated sensitizers improves both their liposome binding and singlet oxygen production, (2) that having the trans form (A 2 B 2 ) improves binding and singlet oxygen production and (3) that the R-groups should be carefully balanced between not too hydrophobic, yet not too hydrophilic. These findings tie in well with recent cellular experiments on a similar set of molecules (18,19).…”

Re-examination of the emission properties of alkoxy- and thioalkyl-substituted phthalocyanines

“…p * in origin this assignment would still be problematic, however. The wavelength of violet emission lies significantly to the blue of a significant portion of the band envelope in the 400-600 nm region, both in the case of Zna(OC 4 H 9 ) 8 Pc [2][3][4][5][6][7][8][9][10][11][12][13][14] and the mixed alkoxy-and thioalkyl-substituted porphyrazines reported by Hoffman and coworkers [15,16]. This pattern can be observed in the emission spectra recorded during the irradiation of a tetrahydrofuran (THF) solution of H 2 a(SC 4 H 9 ) 8 Pc, Fig.…”

“…In its simplest perimeter model description [22][23][24][25], the optical spectroscopy of symmetric metal porphyrin (MP) complexes can be described based on a consideration of perturbations to the molecular orbitals (MOs) arising from the C 16 [26,31]. A weaker Faraday A 1 term that is consistently observed slightly to the red of the B1 band at ca.…”

“…Sulfonated AlClPcs are currently being used commercially for this purpose in Russia [2]. In the emission spectra of alkoxy-and thioalkyl-substituted phthalocyanines and porphyrazines [3][4][5][6][7][8][9][10][11][12][13][14][15][16], an S 1 emission peak is observed in the 600-900 nm region, while a second higher energy peak has also frequently been reported in the 400-600 nm region. The higher energy emission has been assigned as S 2 emission and np * excited states associated with the lone pairs of the peripheral oxygen and/or sulfur atoms have sometimes been proposed as the origin of this peak [7,[11][12][13][14].…”

Synthesis and characterization of phosphonic acid-substituted porphyrazines

“…

Porphyrazines with phosphonic acid groups on the peripheral positions have been prepared by the cyclotetramerization of 1,2-bis{2-(diethyl phosphonate)ethylthio} maleonitrile and followed by the cleavage of the phosphonate esters with TMSBr.Macrocyclic tetrapyrroles (porphyrin, phthalocyanine and porphyrazine) are subjects of great interest in the areas such as catalysis, photodynamic therapy (PDT) and supramolecular chemistry [1][2][3][4][5][6]. Although porphyrazines have attracted significantly less attention compared to porphyrins and phthalocyanines until recently, they have started to arouse more interest due to their interesting photophysical and supramolecular properties.

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