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  • 1
    Electronic Resource
    Electronic Resource
    New potent sensitizers for photodynamic therapy: 21-oxaporphyrin, 21-thiaporphyrin and 21,23-dithiaporphyrin induce extensive tumor necrosis (1999)
    Springer
    Journal of cancer research and clinical oncology 125 (1999), S. 563-568 
    Details
    ISSN: 1432-1335
    Keywords: Key words Photodynamic therapy ; 21-Thiaporphyrin ; 21 ; 23-Dithiaporphyrin ; 21-Oxaporphyrin ; Mouse fibrosarcoma BFS1
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract New sensitizers for photodynamic therapy (PDT) are reported. These compounds, namely 21-thiaporphyrin, 21,23-dithiaporphyrin and 21-oxaporphyrin, reveal some of the properties required for such therapy. Their physicochemical, chemical and pharmacological features meant that we could use them in the treatment of transplantable BFS1 fibrosarcoma in Balb/c mice. New sensitizers and the well-known chlorin e6 (Ce6) were used in doses of 2.5, 5.0, 7.5 and 10.0 mg/kg body weight, given intraperitoneally and followed by light irradiation, the total light doses being 50, 100 and 150 J/cm2 within 24 h after injection. The effectiveness of new sensitizers in PDT was evaluated with in terms of tumor necrosis intensity, the survival time of treated animals, the rate of tumor response (complete/partial/no response), and skin photosensitivity. These results were compared to results obtained in analogous conditions after Ce6-PDT. Distribution studies revealed that the highest concentration of new compounds occurred within 24 h after injection. The results of these experiments confirmed that 21-thiaporphyrin, 21,23-dithiaporphyrin and 21-oxaporphyrin can be considered as potent tumor photosensitizers that do not exert any unwanted effects, primarily skin photosensitization. We suggest that these porphyrins are possible sensitizers to be applied in clinical PDT.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004320050317
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  • 2
    Electronic Resource
    Electronic Resource
    5,10,15,20-Tetraphenylsapphyrin-Identification of a Pentapyrrolic Expanded Porphyrin in the Rothemund Synthesis (1995)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 1 (1995), S. 68-73 
    Details
    ISSN: 0947-6539
    Keywords: porphyrinoids ; Rothemund synthesis ; sapphyrin ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Rothemund-type condensation of pyrrole and benzaldehyde yields, apart from 5,10,15,20-tetraphenylporphyrin (TPPH2) and inverted tetraphenylporphyrin 2-aza-21-carba-5,10,15,20-tetraphenylporphyrin (CTPPH2), a unique pentapyrrolic macrocyclic molecule with the aromatic nucleus of sapphyrin, namely, 5,10,15,20-tetraphenylsapphyrin (TPSH3). Its unorthodox structural skeleton with an inverted pyrrole ring lying opposite to the bipyrrole unit accounts for the spectroscopic properties of the novel sapphyrin. The diprotonation of TPSH3 acts as a trigger for a structural transformation involving a flip of the pyrrole units, which relocates the 27-NH pyrrolic nitrogen from the periphery into the center of the macrocycle. The formation of 5,10,15,20-tetraphenylsapphyrin proves that the pentapyrrolic product is accessible by the mechanism of the Rothemund synthesis.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19950010111
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  • 3
    Electronic Resource
    Electronic Resource
    Nickel Complexes of 21-Oxaporphyrin and 21, 23-Dioxaporphyrin (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 268-278 
    Details
    ISSN: 0947-6539
    Keywords: heterocycles ; heteroporphyrins ; nickel ; porphyrinoids ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The nickel(I) and nickel(II) complexes of 5,20-bis(p-tolyl)-10, 15-diphenyl-21-oxaporphyrin (ODTDPPH) and 5,10,15,20-tetraphenyl-21, 23-dioxaporphyrin (O2TPP) have been investigated. These oxa analogues of 5,10,15,20-tetraarylporphyrin, where one or two pyrrole rings are replaced by a furan moiety, have been synthesized by condensation of the respective precursors, namely 2,5-bis(arylhydroxymethyl)furan, pyrrole, and arylaldehyde. Insertion of nickel(II) into ODTDPPH or O2TPP yielded high-spin five- and six-coordinate ([(ODTDPP)NiIICl] and [(O2TPP)NiIICl2]) complexes, which can be reduced with moderate reducing reagents. The EPR spectra of [(ODTDPP)NiI] and [(O2TPP)NiICl] revealed the NiI oxa(dioxa)porphyrin rather than a NiI anion radical electronic structure. In the structures of [(ODTDPP)NiIICl], [(O2TPP)NiIICl2], and [(ODTDPP)NiI], determined by X-ray diffraction, the furan ring is planar and coordinates in the η1 fashion through the trigonal oxygen atom; the nickel ion lies in the furan plane for the latter two complexes, but slightly outside it in [(ODTDPP)NiIICl]. The Ni-N and Ni-O bond lengths decrease upon reduction of high-spin five-coordinate [(ODTDPP)NiIICl] to four-coordinate [(ODTDPP)NiI]. The pattern of downfield pyrrole resonances in 1H NMR spectra of [(ODTDPP)NiIICl] and [(O2TPP)-NiIICl2] has been established. The downfield positions of furan resonances are unusual for NiII heteroporphyrins; they have been accounted for by the nearly in-plane coordination of the furan moiety as opposed to the side-on coordination found for thiophene- or selenophene-containing heteroporphyrins. An example of ion-pair formation, [(O2TPPH)2][NiIICl4], was produced from [(O2TPP)NiIICl2] by acidification with HCl.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030216
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  • 4
    Electronic Resource
    Electronic Resource
    1H nuclear magnetic resonance studies of the reaction of iron(III) porphyrin cation radical with aryl Grignard reagents (1993)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 31 (1993), S. S47 
    Details
    ISSN: 0749-1581
    Keywords: 1H NMR ; 2H NMR ; Iron ; Porphyrin ; Isoporphyrin ; Tetraphenylporphyrin ; N-Phenyltetraphenylporphyrin ; Aryl Grignard reagents ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Addition of aryl Grignard reagents to an iron(III) tetraphenylporphyrin π cation radical, [(TPP⋅)FeIIICl] (SbCl6), in dichloromethane solution at 202 K yields a mixture of σ-phenyl iron(IV) tetraphenylporphyrin, [(TPP)FeIV(Ph)] (SbCl6), and σ-phenyl iron(III) tetraphenylporphyrin, (TPP)FeIIICl. A σ-phenyliron(III) complex is also formed by nucleophilic addition to the tetraphenylporphyrin macrocycle accompanied by σ-phenyl axial coordination. The complexes formed were identified by 1H NMR spectroscopy. A new route for generating σ-aryl iron(IV) porphyrin species from the iron(III) porphyrin π cation radical was established. The characteristic 1H NMR pattern of the low-spin iron(III) porphyrin ring modified species reflects its Cs symmetry and includes four upfield-shifted pyrrole resonances (2.31, -10.40, 20.39 and -20.87 ppm, 202 K) accompanied by a set of σ-phenyl resonances (ortho, -188.4; p-H, -102.5; p-CH3 for σ-p-tolyl, 162.3 ppm). Analysis of the paramagnetic shifts of the σ-phenyl (σ-p-tolyl) ligand of the new species indicates a high π spin density consistent with the electronic structure of low-spin iron(III) and the contribution of a σ-delocalization mechanism via donation from a filled σ-phenyl orbital to an empty dz2; orbital. The formation of a low-spin σ-phenyliron(III) isoporphyrin or low-spin σ-phenyl N-arylporphyrin is considered. The meso substitution can be accounted for by a mechanism which emphasizes the radical nature of the reaction substrate and involves the formation of σ-transient forms.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1260311311
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  • 5
    Electronic Resource
    Electronic Resource
    Alteration of the Reactivity of a Tellurophene Within a Core-Modified Porphyrin Environment: Synthesis and Oxidation of 21-TelluraporphyrinThis work was supported by the State Committee for Scientific Research KBN of Poland (Grant 2.0732 91 01) and the U. S. National Science Foundation (Grant INT-9114389). (1995)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 34 (1995), S. 2252-2254 
    Details
    ISSN: 0570-0833
    Keywords: oxidations ; porphyrinoids ; tellurium compounds ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.199522521
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