Synthesis, photophysical properties and sugar-dependent in vitro photocytotoxicity of pyrrolidine-fused chlorins bearing S-glycosides

Hirohara, Shiho; Obata, Makoto; Alitomo, Hiroki; Sharyo, Kohei; Ando, Tetsu; Tanihara, Masao; Yano, Shigenobu

doi:10.1016/j.jphotobiol.2009.07.007

Cited by 53 publications

(50 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The latter compounds were used for DNA photocleavage studies with the Pd(II) complex 69 exhibiting the best activity [171] . More details on other examples of A 4 -type glycoporphyrins (70-108) will be given below and are listed in Table 1 [172][173][174][175][176][177][178][179][180][181][182][183] . Pyrrole condensation reaction may also be employed for the preparation of dodecasubstituted porphyrins.…”

Section: A 4 -Type Porphyrinsmentioning

confidence: 99%

“…The photophysical properties showed the S-glycosylated chlorins to have molar extinction coefficients of the Q band twice that of the corresponding unconjugated derivative. These compounds were also investigated for their in vitro photocytotoxicity in HeLa cells [178] . In a similar way, Drain and coworkers extended from previous work on the synthesis of thioglycosylated porphyrins (95 and 91) [247] to form their 1,3-dipolar cycloadducts, i.e.…”

Section: 3-dipolar Cycloadditionsmentioning

confidence: 99%

“…In general, the compounds with asymmetric substitution of saccharide units are more phototoxic than symmetrical compounds [201] . An example of a different class of meso substituted chlorins are compounds 541a', 542b', 542a and 542b which were tested for their photocytotoxicity in HeLa cells [178] . No dark toxicity was found at 0.5 μM.…”

Section: Hydroporphyrinsmentioning

confidence: 99%

“…Wavelengths > 500 nm are usually employed for PDT treatment, therefore the S-glycosylated chlorins have better photophysical properties for PDT compared to the Oglycosylated TPCs [178] . The difference in photoactivity is not attributed to the photophysics as all the compounds have similar properties therefore is due to biological effect.…”

Section: Hydroporphyrinsmentioning

confidence: 99%

“…While often heavy atom effects are noted in solution of in vitro studies, there is no guarantee that it is maintained in a multicellular environment [307] . It is more efficient to attempt to improve the PS efficacy through the sugar unit [177,178,354] . Benzochlorins have been of interest in PDT for a significant time [355] .…”

Section: Hydroporphyrinsmentioning

confidence: 99%

See 4 more Smart Citations

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

View full text Add to dashboard Cite

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.

show abstract

Section: A 4 -Type Porphyrinsmentioning

confidence: 99%

Section: 3-dipolar Cycloadditionsmentioning

confidence: 99%

Section: Hydroporphyrinsmentioning

confidence: 99%

Section: Hydroporphyrinsmentioning

confidence: 99%

Section: Hydroporphyrinsmentioning

confidence: 99%

See 3 more Smart Citations

Chemical Synthesis and Medicinal Applications of Glycoporphyrins

Moylan¹,

Scanlan²,

Senge

2015

CMC

View full text Add to dashboard Cite

show abstract

Synthesis and Biological Evaluation of a Library of Glycoporphyrin Compounds

Daly

Vaz

Davies

et al. 2012

Chemistry A European J

View full text Add to dashboard Cite

A library of glycosylated porphyrins (Glycoporphyrins) was prepared and evaluated for their PDT activity against oesophageal squamous cell carcinoma cell line OE21 in vitro. Synthetic methodology was developed to allow incorporation of biologically active carbohydrates including the histo blood group antigen trisaccharide, Lewis x onto the porphyrin backbone. The effect of the carbohydrate group and substitution pattern on the PDT activity, cell uptake and subcellular localisation of the glycoporphyrin compounds is reported.

show abstract