Meso-substituted tetra-cationic porphyrins photosensitize the death of human fibrosarcoma cells via lysosomal targeting

Ricchelli, Fernanda; Franchi, Lisa; Miotto, Giovanni; Borsetto, Lara; Gobbo, Silvano Del; Nikolov, P.; Bommer, Jerry C.; Reddi, Elena

doi:10.1016/j.biocel.2004.06.013

Cited by 59 publications

(50 citation statements)

References 28 publications

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“…Instead, they were shown to localise in lysosomes of human HT1080 fibrosarcoma cells, and there was no evidence of intracellular redistribution of the PS during PDT which probably resulted in necrosis. Lipophilicity was named in this case as a main factor that influenced the cellular uptake (by endocytosis), distribution and localisation (in lysosomes), and resulted in higher PDT efficiency of the PSs with longer alkyl chains (Ricchelli et al 2005). …”

Section: Mitochondrial Targetingmentioning

confidence: 99%

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

2017

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Photodynamic therapy (PDT) combines a photosensitiser, light and molecular oxygen to induce oxidative stress that can be used to kill pathogens, cancer cells and other highly proliferative cells. There is a growing number of clinically approved photosensitisers and applications of PDT, whose main advantages include the possibility of selective targeting, localised action and stimulation of the immune responses. Further improvements and broader use of PDT could be accomplished by designing new photosensitisers with increased selectivity and bioavailability. Porphyrin-based photosensitisers with amphiphilic properties, bearing one or more positive charges, are an effective tool in PDT against cancers, microbial infections and, most recently, autoimmune skin disorders. The aim of the review is to present some of the recent examples of the applications and research that employ this specific group of photosensitisers. Furthermore, we will highlight the link between their structural characteristics and PDT efficiency, which will be helpful as guidelines for rational design and evaluation of new PSs.

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Section: Mitochondrial Targetingmentioning

confidence: 99%

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

2017

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“…Positively charged porphyrins proved to accumulate more readily in cultured cells, suggesting a significant electrostatic contribution (Lambrechts et al 2004;Ricchelli et al 2005;). …”

Section: Introductionmentioning

confidence: 99%

Oligo- and polypeptide conjugates of cationic porphyrins: binding, cellular uptake, and cellular localization

et al. 2017

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Recently we have characterized the DNA and nucleoprotein (NP) binding of bis(4-Nmethylpyridyl)-15,20-di(4-carboxyphenyl)porphyrin (BMPCP) and meso-tri(4-Nmethylpyridyl)-mono(4-carboxyphenyl)porphyrin (TMPCP) and their tetra-peptide conjugates (BMPCP-4P 2 and TMPCP-4P, respectively). In this work we investigated the interaction of TMPCP conjugated to the tetra-peptide branches of branched chain polymeric polypeptide with poly-L-lysine backbone (AK) with DNA or NP using spectroscopic methods.Analysis of absorption spectra revealed the external binding, but no intercalation of TMPCP-AK to DNA. There was no evidence for the interaction between TMPCP-AK and encapsidated DNA. Furthermore, we examined the cellular uptake of BMPCP and TMPCP and their tetra-or polypeptide conjugates by flow cytometry and analyzed how charge, size and structure of the compounds affect their incorporation. In comparison, liposomal association constants of these derivatives were determined. BMPCP-4P 2 accumulated the most, and porphyrins with two positive charges (BMPCP and BMPCP-4P 2 ) showed better accumulation than the tri-cationic TMPCP or TMPCP-4P.Cellular uptake of polycationic TMPCP-AK was significantly lower than that of the free or tetra-peptide conjugated derivatives. The sub-cellular localization of all the five compounds was investigated in co-localization studies by confocal microscopy with special attention to their nuclear localization. Neither free nor conjugated BMPCP or TMPCP were co-localized with nuclear marker. Instead, these derivatives showed co-localization with lysosomal and mitochondrial fluorescent probes. TMPCP-AK conjugate had different localization pattern appearing mainly in mitochondria and cytoplasmic vesicles.Our results may contribute to the further design of DNA targeting porphyrin based constructs.

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“…The structure changes between the intermediates and the final products were showed clearly by the resonance changes in the It is worth noting that in this condensation method only the E-isomer was formed, which was further confirmed by the 1 H NMR spectrum of the corresponding chlorin e 6 , and purpurinimide condensational derivatives (5,12).…”

mentioning

confidence: 54%

“…4, 7, 11), obtained by a sequence of reactions [10][11][12][13][14] from chlorophyll a, were refluxed with 4-picoline in acetic anhydride and several drops of acetic acid to afford the desired pyridyl chlorins (5,8,12) with 60-65% yields. 15 The structure of the pyridyl chlorins was determined by 1 H NMR, HRMS, UVvis spectra and elemental analysis.…”

mentioning

confidence: 99%

Aldol-Like Carbon-Carbon Condensation for Pyridyl Substituted Chlorins

Li¹,

Cui²,

Wang³

2011

Bulletin of the Korean Chemical Society

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Meso-substituted tetra-cationic porphyrins photosensitize the death of human fibrosarcoma cells via lysosomal targeting

Cited by 59 publications

References 28 publications

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

Oligo- and polypeptide conjugates of cationic porphyrins: binding, cellular uptake, and cellular localization

Aldol-Like Carbon-Carbon Condensation for Pyridyl Substituted Chlorins

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