Metalloporphyrins as chemical shift reagents: the unambiguous NMR characterization of the cis- and trans-isomers of meso-(bis)-4′-pyridyl-(bis)-4′-carboxymethylphenylporphyrins

Gianferrara, Teresa; Giust, Davide; Bratsos, Ioannis; Alessio, Enzo

doi:10.1016/j.tet.2007.03.135

Cited by 17 publications

(11 citation statements)

References 19 publications

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“…Along this strategy, that was used already for Pt and Ru-polypyridyl conjugates, 8,32 we prepared the series of meso-pyridyl/carboxyphenyl porphyrins with the aim of exploiting the pyridyl N atoms for coordination to Ru fragments and the deprotonation of the carboxylic groups at physiological pH for increasing water solubility. 42 We report here the monoruthenated adduct Na[trans-RuCl 4 (dmso-S)(4¢-MPyCbPP)] (5, Fig. 6), where 4¢-MPyCbPP = 5-(4¢-pyridyl)-10,15,20-tris(4¢carboxyphenyl)porphyrin, in which the coordination sphere of Ru(III) is again very similar to that of NAMI.…”

Section: Conjugates Through Single-bond Coordinationmentioning

confidence: 82%

Synthetic strategies towards ruthenium–porphyrin conjugates for anticancer activity

et al. 2009

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The conjugation of porphyrins to metal fragments is a strategy for making new compounds that are expected to combine the phototoxicity and the tumour-localization properties of the porphyrin chromophore with the cytotoxicity of the metal fragment for additive antitumour effect. We report here the preparation of new classes of porphyrin-ruthenium conjugates with potential bio-medical applications. Ruthenium was chosen because several Ru compounds have shown promising anticancer activity. The conjugation with the porphyrin moiety was accomplished either through peripheral pyridyl rings (e.g.meso-4'-tetrapyridylporphyrin, 4'TPyP) or through bpy units (e.g.meso-(p-bpy-phenyl)porphyrins, bpy(n)-PPs, n = 1-4). The number of Ru fragments attached to the porphyrins ranges from 1 to 4 and the total charge of the conjugates from -4 to +8. Different types of peripheral fragments, both Ru(III) and Ru(II), have been used: in some cases they are structurally similar to established anticancer compounds. Examples are [Na](4)[4'TPyP{trans-RuCl(4)(dmso-S)}(4)] (2), that bears four NAMI-type Ru(III) fragments, or [4'TPyP{Ru([9]aneS3)(en)}(4)][CF(3)SO(3)](8) (3) and [bpy(4)-PP{Ru([9]aneS3)(dmso-S)}(4)][CF(3)SO(3)](8) (9) (en = ethane-1,2-diamine, [9]aneS3 = 1,4,7-trithiacyclononane) that have four half-sandwich Ru(II) compounds. The Ru fragments may either contain one or more labile ligands, such as in 2 or in 9, or be coordinatively saturated and substitutionally inert, such as in 3 or in [bpy(4)-PP{Ru([12]aneS4)}(4)][CF(3)SO(3)](8) (11) ([12]aneS4 = 1,4,7,10-tetrathiacyclododecane). Most of the ruthenium-porphyrin conjugates described in this work are soluble--at least moderately--in aqueous solution and are thus suitable for biological investigations, in particular for cytotoxicity and photo-cytotoxicity tests.

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Section: Conjugates Through Single-bond Coordinationmentioning

confidence: 82%

Synthetic strategies towards ruthenium–porphyrin conjugates for anticancer activity

et al. 2009

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“…From 1D 1 H NMR spectra, it is clear that the porphyrins (TPPOH-2Tris trans and TPPOH-2Tris cis ) have two Tris groups considered to be cis or trans isomers of the porphyrin. The isomers (cis and trans) of the porphyrin cannot be distinguished by conventional spectroscopic techniques and are separated according to R f values in the mixture by column chromatography . The 1D 1 H NMR spectra of the cis and trans forms of the porphyrin are almost identical .…”

Section: Resultsmentioning

confidence: 99%

From Simplicity to Complexity in Grafting Dawson-Type Polyoxometalates on Porphyrin, Leading to the Formation of New Organic–Inorganic Hybrids for the Investigation of Third-Order Optical Nonlinearities

et al. 2019

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“…All reaction solvents were dried and purified according to standard procedures. The 5-(4-methoxyphenyl)-10,15,20tri(pyridin-4-yl) porphyrin (1) was synthesized according to literature method [20]. Diethyl phosphorochloridate was synthesized according to the literature [21], and dimethyl (3-bromopropyl)phosphonate was prepared following the literature [22].…”

Section: Methodsmentioning

confidence: 99%

“…The water-soluble porphyrin P1, which was used as the control compound in our bioactivity studies, was synthesized as described in the literature [20]. The syntheses of porphyrin-phosphonate conjugates P2 and P3 were carried out as shown in Scheme 1.…”

Section: Preparation Of Porphyrin-phosphonate Conjugatesmentioning

confidence: 99%

Water-soluble porphyrin-phosphonate conjugates as potential photodynamic therapy photosensitizers

Chen

et al. 2015

J. Porphyrins Phthalocyanines

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Metalloporphyrins as chemical shift reagents: the unambiguous NMR characterization of the cis- and trans-isomers of meso-(bis)-4′-pyridyl-(bis)-4′-carboxymethylphenylporphyrins

Cited by 17 publications

References 19 publications

Synthetic strategies towards ruthenium–porphyrin conjugates for anticancer activity

Synthetic strategies towards ruthenium–porphyrin conjugates for anticancer activity

From Simplicity to Complexity in Grafting Dawson-Type Polyoxometalates on Porphyrin, Leading to the Formation of New Organic–Inorganic Hybrids for the Investigation of Third-Order Optical Nonlinearities

Water-soluble porphyrin-phosphonate conjugates as potential photodynamic therapy photosensitizers

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