Synthesis of neutral and cationic tripyridylporphyrin-d-galactose conjugates and the photoinactivation of HSV-1

Tomé, João P. C.; Silva, Eduarda M. P.; Pereira, Ana; Alonso, Cristina; Faustino, Maria A. F.; Neves, Maria G. P. M. S.; Tomé, Augusto C.; Cavaleiro, José A. S.; Tavares, Sabina A.P.; Duarte, Ricardo R.; Caeiro, Maria Filomena; Valdeira, Maria Luísa

doi:10.1016/j.bmc.2007.05.005

Cited by 52 publications

(33 citation statements)

References 30 publications

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“…Silva et al have tested several cationic β-vinyl substituted meso-tetraphenolyporphyrins at non-cytotoxic concentrations and efficiently inhibited cell-free HSV-1 (>99%), but, interestingly, the authors noted that compounds with strikingly similar chemical structures showed dramatically different inhibitory activity on HSV-1 (Silva et al 2005). Another recent study showed that neutral glycoporphyrins having unprotected hydoxy groups and galactopyranoside can effectively inhibit infectivity of HSV-1 and HSV-2, which was even comparable to acyclovir and foscarnet at non-toxic cell concentrations (Tome et al 2005(Tome et al , 2007. Surprisingly, in contrast to phtalocyanines which were active only if infected cells were treated early during the infection (Smetana et al 1994), inhibition of intercellular virus was possible even 16 h after infection (Tome et al 2005(Tome et al , 2007.…”

Section: Antiviral Pact and Porphyrin-based Cationic Amphiphilic Pssmentioning

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: Antiviral Pact and Porphyrin-based Cationic Amphiphilic Pssmentioning

confidence: 99%

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

2017

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“…With the exception of 416a all compounds gave IC 50 Earlier it had been shown that the fully deprotected derivative have the best activity [30] . Here, both 416c and 415 significantly reduced the HSV-1 yield in vero cells; additionally the cationic derivative exhibited dark toxicity at all times of the viral replication cycle [229] . Another approach used supramolecular aggregates of positively charged amphiphilic cyclodextrins with 5-[4-(1-dodecanoylpyridinium)]-10,15,20-triphenylporphyrin (TDPyP).…”

Section: Antiviral and Antifungal Pdtmentioning

confidence: 88%

“…Similar concepts can also be employed to prepare unsymmetrical cationic glycoporphyrins. In an extension of previous work on the synthesis of neutral glycoporphyrins which displayed good inactivation of herpes simplex virus (HSV-1 and HSV-2) [30] Tomé et al synthesized glycosylated neutral and cationic tripyridylporphyrins and evaluated their antiviral activity [229] . The porphyrin starting material 412 was synthesized via crossed Rothemund reaction which underwent a one-pot conversion to the activated ester 413 by reaction with thionyl chloride and addition of N-hydroxysuccinimide.…”

Section: Glycosidation Reactions O-linked Systemsmentioning

confidence: 99%

“…[Gram (−)] which were resistant to UV inactivation [230] . Glycoporphyrins 416b,c [229] and the non-glycoconjugate 73 [174] served as controls. The latter compound was used as a precursor for the synthesis of the mono-charged derivatives 209 and 210 and tetra-charged porphyrin derivatives (74, 211, 212).…”

Section: Glycosidation Reactions O-linked Systemsmentioning

confidence: 99%

“…These compounds display significant inhibitory effects and offer potential for the treatment of herpes virus infections [30] . Another broad study compared the antiviral effect of neutral porphyrins (412,414,415) and their cationic analogues (416a-c) against HSV-1 [229] . With the exception of 416a all compounds gave IC 50 Earlier it had been shown that the fully deprotected derivative have the best activity [30] .…”

Section: Antiviral and Antifungal Pdtmentioning

confidence: 99%

See 2 more Smart Citations

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

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Abstract:This review presents an in-depth overview of the modification of porphyrins with bioconjugates and their applications in medicine today. Porphyrin bioconjugates ranging from nucleotides to steroids are under active scrutiny. However, carbohydrates have been at the forefront of such research in recent years and offer significant potential. This is attributed to their own selectivity to lectins on the surface of cancer cells and their influence on the amphiphilicity of the porphyrin macrocycle. These characteristics and the tendency of porphyrin photosensitizers to accumulate in tumor tissues make glycoporphyrins promising candidates for use as photosensitizers. Thus, a detailed overview of the synthesis and biological evaluation of glycoporphyrins is given with a particular focus on their applications in photodynamic therapy and their future prospects as drug candidates have been reported.

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Suzuki‐Miyaura Reaction of Glycals with Base‐Labile Protecting Groups as a New Route to Glycoporphyrins

Godlewski,

Malinowski

2024

Adv Synth Catal

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Glycoporphyrins are considered promising photosensitisers of new generation. Herein, we describe the original, metal‐catalysed method towards porphyrin‐carbohydrate C‐C conjugates. The protocol of Suzuki‐Miyaura reaction has been developed and it was compatible with peracetylated 2‐iodoglycals. The utility of the reaction was exemplified on 15 different (C‐2)‐arylated sugar derivatives. Then it was applied on more challenging starting materials, namely, porphyrin boronates in which we addressed the issues of difficult transmetalation step usually observed on palladium‐catalysed processes of porphyrin derivatives. The efficiency of the protocol was finally applied to synthesize the library of glycoporphyrins proving the versatile character of this strategy. Keywords: Suzuki‐Miyaura reaction, glycoporphyrins, photosensitisers, carbohydrates, porphyrins, palladium catalysis, glycal

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Synthesis of neutral and cationic tripyridylporphyrin-d-galactose conjugates and the photoinactivation of HSV-1

Cited by 52 publications

References 30 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

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Suzuki‐Miyaura Reaction of Glycals with Base‐Labile Protecting Groups as a New Route to Glycoporphyrins

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