Novel porphyrinoids

Vogel, E.

doi:10.1351/pac199062030557

Cited by 126 publications

(52 citation statements)

References 2 publications

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“…[1][2][3][4][5][6][7] In relation to Hückels aromaticity rules, three annulenic models of porphyrins were practical in describing their electronic structure. A porphyrin may be regarded as 1) a tetraaza [16]annulene dianion with four À C 2 H 2 À bridges containing isolated double bonds, [8,9] or 2) a [20]annulene dication with two neutral bivalent NH and two negatively charged À N À links.…”

Section: Introductionmentioning

confidence: 99%

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A Flexible Porphyrin–Annulene Hybrid: A Nonporphyrin Conformation formeso‐Tetraaryldivacataporphyrin

Pacholska‐Dudziak¹,

Szterenberg²,

Latos‐Grażyński³

2011

Chemistry A European J

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An annulene-porphyrin hybrid, the diaaza-deficient porphyrin 5,10,15,20-tetraaryl-21,23-divacataporphyrin, has been synthesized by an extrusion of tellurium atom(s) from 5,10,15,20-tetraaryl-21,23-ditelluraporphyrin under treatment with HCl. In addition, a monoaza-deficient 5,10,15,20-tetraaryl-21-tellura-23-vacataporphyrin was formed in the same reaction. The two new members of the vacataporphyrin family were characterized by X-ray crystallography, as well as UV/Vis and NMR spectroscopy. These aromatic molecules preserve the fundamental structural and spectroscopic features of the parent tetraarylporphyrin. The X-ray crystal structures of 21,23-divacataporphyrin and 21-tellura-23-vacataporphyrin show typical porphyrin patterns. The molecules are not strictly planar and show distortion of the annulene moieties. The N22⋅⋅⋅N24 distances (5.23 and 5.09 Å) are considerably longer than in regular porphyrins. For 21,23-divacataporphyrin, variable-temperature (1)H NMR spectroscopy data allowed the identification of divacataporphyrin stereoisomers differentiated by the geometry of the butadiene bridges. The forms remain in thermodynamic equilibrium.

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Section: Introductionmentioning

confidence: 99%

“…[7,14] To date, hydrocarbon 6, named quatyrin, [15,16] has yet be synthesized, although the importance of 6 in both annulene and porphyrin fields has…”

Section: Introductionmentioning

confidence: 99%

A Flexible Porphyrin–Annulene Hybrid: A Nonporphyrin Conformation formeso‐Tetraaryldivacataporphyrin

Pacholska‐Dudziak¹,

Szterenberg²,

Latos‐Grażyński³

2011

Chemistry A European J

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“…This tumour model has been used before for the study of microcirculation in neoplastic tissue (Asaishi et al, 1981;Endrich et al, 1982). Porphycenes were selected as pure porphyrin model compounds for their high absorption and fluorescence yields (Aramendia et al, 1986; KreimerBirnbaum, 1989) and their well-established chemistry (Vogel, 1990 of polar substitutents and thus in lipophilicity. The ether, ester, hydroxy and carboxy groups present in these porphycenes are those functionalities found in the analysis of Photofrin (Pandey et al, 1990).…”

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confidence: 99%

Tumour localisation kinetics of photofrin and three synthetic porphyrinoids in an amelanotic melanoma of the hamster

Leunig

Richert²,

Gamarra³

et al. 1993

Br J Cancer

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Summary In this study the localisation of porphyrinoid photosensitisers in tumours was investigated. To determine if tumour selectivity results from a preferential uptake or prolonged retention of photosensitisers, intravital fluorescence microscopy and chemical extraction were used. Amelanotic melanoma (A-Mel-3) were implanted in a skin fold chamber in Syrian Golden hamsters. Distribution of the porphyrin mixture Photofrin and three porphycenes, pure porphyrinoid model compounds, was studied quantitatively by intravital fluorescence microscopy. Extraction of tissue and blood samples was performed to verify and supplement intravital microscopic results. Photofrin accumulated in melanomas reaching a maximum tumour:skin tissue ratio of 1.7:1. Localisation of the different porphycenes was found to be highly tumour selective (3.2:1), anti-tumour selective (0.2:1), and non-selective (1:1) with increasing polarity of the porphycenes. The two non-tumour selective porphycenes had distinctly accelerated serum and tissue kinetics; serum halflife times being as short as 1 min. The specific localisation of the slowly distributed, tumour selective photosensitisers, occurred exclusively during the distribution from serum and uptake into tissues. For the most selective porphycene, the tumour selection process had a halflife of 260 ± 150 min and led to a strongly fluorescent tumour edge edema. Accumulation of porphyrines by the amelanotic melanoma (A-Mel-3) can be attributed to an enhanced uptake rate for lipophilic molecules in this subcutaneously growing neoplasm. The slow distribution of the two tumour specific photosensitisers and the strong fluorescence of these hydrophobic molecules in the tumour compartment with a high water content indicate a carrier role of serum proteins in the selection process. Enhanced permeability of the tumour vasculature to macromolecules appears to be the most probable reason for the tumour selectivity of these two sensitisers.In the first half of this century it was shown that systemically administered porphyrines preferentially localise in neoplasms of tumour-bearing animals (Policard, 1924;Auler et al., 1942). This phenomenon found diagnostic application as a method for tumour detection utilising the red fluorescence of the porphyrines (Lipson et al., 1961a,b;Baumgartner et al., 1987). The photosensitising properties of these molecules (Meyer-Betz, 1913) were exploited for therapeutic purposes and allowed the establishment of photodynamic therapy (PDT) as a new treatment modality for tumours (Dougherty et al., 1978).The mechanisms leading to the tumour specific localisation of the porphyrines are still under investigation (Moan et al., 1992). Experimental progress has been complicated by the fact that even the most purified photosensitiser, Photofrin (Pf), is a complex mixture of molecular species with very similar spectral characteristics (Dougherty, 1987;Pandey et al., 1990).In the present investigation, the localisation of three chemically pure synthetic porphyrinoids in an amelanotic mel...

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“…Provided that this formal analogy exists, a symbiotic relationship between annulene and porphyrin chemistry might be established. [8] Pursuing this idea resulted in the design and preparation of porphycene (87), the most attractive of the six conceivable constitutional isomers of porphyrin with a N 4 core, molecules which nature appears to have forgotten.…”

Section: Porphycene and Other Structural Variants Of Porphyrinmentioning

confidence: 99%

From Small Carbocyclic Rings to Porphyrins: A Personal Account of 50 Years of Research

Vogel¹

2011

Angew Chem Int Ed

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Novel porphyrinoids

Abstract: Abstract

Cited by 126 publications

References 2 publications

A Flexible Porphyrin–Annulene Hybrid: A Nonporphyrin Conformation formeso‐Tetraaryldivacataporphyrin

A Flexible Porphyrin–Annulene Hybrid: A Nonporphyrin Conformation formeso‐Tetraaryldivacataporphyrin

Tumour localisation kinetics of photofrin and three synthetic porphyrinoids in an amelanotic melanoma of the hamster

From Small Carbocyclic Rings to Porphyrins: A Personal Account of 50 Years of Research

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