Strategies toward the synthesis of amphiphilic porphyrins

Pisarek, Sabina; Maximova, Ksenia; Gryko, Dorota

doi:10.1016/j.tet.2014.05.090

Cited by 48 publications

(39 citation statements)

References 233 publications

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“…heme) have both hydrophilic (polar head) and hydrophobic (tail) moieties. Hydrophilic moieties derive from charged or uncharged polar head groups, and additional hydrophobic moieties most often from hydrocarbon (alkyl) chains (Pisarek et al 2014). Cationic amphiphilic porphyrin-based PSs obtained completely by synthesis are mostly meso-substituted porphyrins with different symmetry patterns, free or in complex with metal (Caminos et al 2006;Lazzeri and Durantini 2003).…”

Section: Types Of Porphyrin-based Cationic Amphiphilic Pssmentioning

confidence: 99%

“…The synthesis of the most common cationic amphiphilic porphyrins was reviewed recently by Pisarek et al (2014). The largest fraction of cationic amphiphilic porphyrins are 2-, 3-or 4-pyridinium salts, obtained by alkylation of 2-, 3-or 4-pyridylporphyrins with alkyl halides of different chain lengths.…”

Section: Synthesis Of Amphiphilic Pssmentioning

confidence: 99%

“…Lipophilicity of all these compounds can easily be increased by increasing the number of carbons in the alkyl chains and/or decreasing the number of cations. Notably, monocationic porphyrins are usually not water-soluble, while cis isomers are less hydrophobic than trans isomers and considered better amphiphiles, thanks to the welldefined head/tail structure (Pisarek et al 2014). There are also ammonium and phosphonium salts as cationic amphiphiles, but phosphonium groups are more lipophilic and were considered less favourable for PS structure due to self-aggregation because of the interactions of highly polarisable phosphonium cation with the highly polarisable porphyrin π-surface (Jin et al 1997).…”

Section: Synthesis Of Amphiphilic Pssmentioning

confidence: 99%

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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: Types Of Porphyrin-based Cationic Amphiphilic Pssmentioning

confidence: 99%

Section: Synthesis Of Amphiphilic Pssmentioning

confidence: 99%

Section: Synthesis Of Amphiphilic Pssmentioning

confidence: 99%

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

2017

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“…Challenges that must be addressed to realize the full potential of these drugs, however, include synthesis of analogs, determination of pharmacokinetics, targeting, and bioavailability (6,7). We have taken up the challenge of functionalizing metallocorroles to enhance cell permeability (8,9). We hope to achieve this goal while still retaining the inherent therapeutic properties of these macrocyclic compounds.…”

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confidence: 99%

Cellular uptake and anticancer activity of carboxylated gallium corroles

Pribisko

Palmer²,

Grubbs

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

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We report derivatives of gallium(III) tris(pentafluorophenyl)corrole, 1 [Ga(tpfc)], with either sulfonic (2) or carboxylic acids (3, 4) as macrocyclic ring substituents: the aminocaproate derivative, 3 [Ga(ACtpfc)], demonstrated high cytotoxic activity against all NCI60 cell lines derived from nine tumor types and confirmed very high toxicity against melanoma cells, specifically the LOX IMVI and SK-MEL-28 cell lines. The toxicities of 1, 2, 3, and 4 [Ga(3-ctpfc)] toward prostate (DU-145), melanoma (SK-MEL-28), breast (MDA-MB-231), and ovarian (OVCAR-3) cancer cells revealed a dependence on the ring substituent: IC 50 values ranged from 4.8 to >200 μM; and they correlated with the rates of uptake, extent of intracellular accumulation, and lipophilicity. Carboxylated corroles 3 and 4, which exhibited about 10-fold lower IC 50 values (<20 μM) relative to previous analogs against all four cancer cell lines, displayed high efficacy (E max = 0). Confocal fluorescence imaging revealed facile uptake of functionalized gallium corroles by all human cancer cells that followed the order: 4 >> 3 > 2 >> 1 (intracellular accumulation of gallium corroles was fastest in melanoma cells). We conclude that carboxylated gallium corroles are promising chemotherapeutics with the advantage that they also can be used for tumor imaging.

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“…This summary extends a review on water-soluble porphyrins published in the year 2000 [40] that provides a detailed account of the acidbase properties and aggregation behavior of conventional water-soluble porphyrins. A 2014 review on amphiphilic porphyrins by Gryko and co-workers [41] is also available; overlap with this review is minimized and these reviews are thus complementary. Porphyrins linked to sugars, many of which are also water-soluble, have been reported [41][42][43].…”

Section: Introductionmentioning

confidence: 99%

Modifications of Porphyrins and Hydroporphyrins for their Solubilization in Aqueous Media

Luciano

Brückner

2017

Preprint

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Abstract:The increasing popularity of porphyrins and hydroporphyrins for application in a variety of biomedical (photodynamic therapy, fluorescence tagging and imaging, photoacoustic imaging) and technical (chemosensing, catalysis, light harvesting) applications is also associated with the growing number of methodologies that enable their solubilization in aqueous media. Natively, the vast majority of synthetic porphyrinic compounds are not water-soluble. Moreover, any water-solubility imposes several restrictions on the synthetic chemist on when to install solubilizing groups in the synthetic sequence, and how to isolate and purify these compounds. This review summarizes the chemical modifications to render synthetic porphyrins water-soluble, with a focus on the work since 2000. Where available, practical data such as solubility, indicators for the degree of aggregation, and special notes for the practicioner are listed. We hope that this review will guide synthetic chemists through the many strategies known to make porphyrins and hydroporphyrins water soluble.

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Strategies toward the synthesis of amphiphilic porphyrins

Cited by 48 publications

References 233 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

Cellular uptake and anticancer activity of carboxylated gallium corroles

Modifications of Porphyrins and Hydroporphyrins for their Solubilization in Aqueous Media

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