Synthesis of water-soluble phthalocyanines bearing four or eight d-galactose units

Soares, Ana Raquel; Tomé, João P. C.; Neves, Maria G. P. M. S.; Tomé, Augusto C.; Cavaleiro, José A. S.; Torres, Tomás

doi:10.1016/j.carres.2008.12.009

Cited by 69 publications

(46 citation statements)

References 17 publications

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“…With the success of the Si-phthalocyanine derivatives focus turned to the synthesis of the more stable tetra-and monoglycosylated zinc(II) phthalocyanines (Scheme 39). Both galactosyl (also reported by Soares et al [309] , 604) and glucosyl (622) tetra-substituted derivatives were synthesized via DBU-promoted self-cyclisation in the presence of zinc acetate. In addition selectivity for the 1,8,15,22 isomer was observed when bulky groups were placed in the α position affording 625a and 625b from cerium promoted cyclisation reactions followed by metallation by zinc.…”

Section: Title Of Thementioning

confidence: 96%

“…A similar method of direct anomeric linkage was applied by Boyle et al to synthesize a tetragalactose-substituted Zn(II) phthalocyanine (602b) [308] . Similarly, water soluble glycophthalocyanines with four or eight unprotected D-galactose moieties were synthesized for application in PDT [309] . The glycophthalonitrile 603 was tetramerized in the presence of ZnCl 2 , affording phthalocyanine 604 in 43 % yield.…”

Section: Phthalocyaninesmentioning

confidence: 99%

“…Concluding the chloro-derivatives are less potent than 617 [316] . Glycophthalocyanines 605, 608 and 598 [304,309] were investigated for their PDT effect and influence on cell death of HeLa and HaCat cells [359] . The symmetric glycophthalocyanine 598 showed selective targeting with significant higher photocytotoxicity in the cancer cell line compared to non-malignant HaCaT cells.…”

Section: Related Systemsmentioning

confidence: 99%

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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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Section: Title Of Thementioning

confidence: 96%

Section: Phthalocyaninesmentioning

confidence: 99%

Section: Related Systemsmentioning

confidence: 99%

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Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

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“…Saccharide is one of the most appealing choices for conjugation. 11,12 It is generally believed that carbohydrates linked to phthalocyanines would result in improved uptake in cells, particularly in the tumor cells having an overexpression of glucose transporters. 13 To this end, we have synthesized a glucoconjugated silicon(IV) phthalocyanine (SiPcGlu, Fig.…”

Section: Research Papermentioning

confidence: 99%

Photodynamic activity of a glucoconjugated silicon(IV) phthalocyanine on human colon adenocarcinoma

Chan¹,

Lo²,

Yeung³

et al. 2010

Cancer Biology & Therapy

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“…31) (Soares et al 2012). The synthetic access to these phthalocyanines involved the tetramerization of the adequate glycophthalonitrile or glycophthalonitrile and phthalonitrile previously prepared, in N,N-dimethylaminoethanol (DMAE) at 140 ºC, in the presence of ZnCl 2 (Soares et al 2009, Ribeiro et al 2006). …”

Section: Cancer Pdt and Porphyrin-type Derivatives 1003mentioning

confidence: 99%

Cancer, Photodynamic Therapy and Porphyrin-Type Derivatives

Gomes

Cavaleiro

2018

An. Acad. Bras. Ciênc.

Self Cite

105

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This review has two parts. The first one gives an approach to interdisciplinary studies against cancer carried out by many scientists using porphyrin-type substrates as photosensitizers in PDT. Intensive studies were performed for almost six decades. The successes really started in 1993 with the first formulation patented under the trade name Photofrin, which was immediately approved in several countries to treat certain types of cancer. Photofrin is still used although certain negative features soon became well known. That has motivated the search for better new photosensitizers. Several ones were developed, evaluated and a few of them had clinical approval. This group includes porphyrin derivatives and pro-drugs (aminolevulinic acid and its alkyl esters). Oncological, dermatological and ophthalmic applications are now taking place for the benefit of mankind. The second part of this review is related with the work carried out in Aveiro at the authors University on the synthesis and biological evaluation of several potential PDT photosensitizers. Not only new synthetic methodologies mainly for porphyrins and chlorins were developed but also other related macrocycles of the phthalocyanine and corrole types have entered in the same "pipeline". In vivo and in vitro biological evaluations also took place under interdisciplinary studies.

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Synthesis of water-soluble phthalocyanines bearing four or eight d-galactose units

Cited by 69 publications

References 17 publications

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Photodynamic activity of a glucoconjugated silicon(IV) phthalocyanine on human colon adenocarcinoma

Cancer, Photodynamic Therapy and Porphyrin-Type Derivatives

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