Synthesis and in vitro photodynamic activities of water-soluble fluorinated tetrapyridylporphyrins as tumor photosensitizers

Ko, Yoon‐Joo; Yun, Kyung-Jin; Kang, Min-Seok; Park, Jong-Min; Lee, Kyung‐Tae; Park, Seung Bum; Shin, Jonghoon

doi:10.1016/j.bmcl.2007.02.083

Cited by 52 publications

(32 citation statements)

References 25 publications

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“…41,42 The results suggest that carboranylchlorins are good candidates for this dual treatment modality and warrant further investigations. Recently, seven polyamine conjugates of a tri(p-carboranylmethylthio)-tetrafluorophenylporphyrin (33)(34)(35)(36)(37)(38)(39) were prepared in high yields by sequential substitution of the p-phenyl fluoride of tetrakis(pentafluorophenyl)porphyrin (TPPF) (Fig. 9).…”

Section: Porphyrin-polyamine Conjugatesmentioning

confidence: 99%

“…Cytotoxicity tests showed that these porphyrins have no dark toxicity, whilst 23 exhibited good cytotoxicity with ~85% tumor eradication with a light dose of 175 mJ.cm -2 . Water-soluble fluoro-substituted porphyrins were designed for similar studies by Ko et al 34 Of the porphyrins 24-27 the latter two exhibited significantly higher photocytotoxicity on HeLa cells. IC 50 values were 0.87 µM for porphyrin 26 and 1.1 µM for porphyrin 27, while IC 50 values of 3 µM and 40 µM were obtained for 24 and 25 respectively.…”

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confidence: 99%

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Current Developments in Using MESO-(TETRA) Substituted Porphyrins for PDT

Shaker¹,

Sweed²,

Moylan³

et al. 2016

Handbook of Photodynamic Therapy

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Section: Porphyrin-polyamine Conjugatesmentioning

confidence: 99%

mentioning

confidence: 99%

Current Developments in Using MESO-(TETRA) Substituted Porphyrins for PDT

Shaker¹,

Sweed²,

Moylan³

et al. 2016

Handbook of Photodynamic Therapy

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“…Fluorinated derivatives of m-or p-linked meso-pyridyl porphyrins were prepared along Adler synthesis routes [73]. N-Alkylation of the pyridyl substituents by treatment with (CH3)3O + BF4 -afforded the tetra-alkylated products 32 and 33, respectively as their tetrafluoroborate salts.…”

Section: Scheme 8 Quarternization Options Of Meso-tetrakis(4-pyridylmentioning

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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“…4 General procedure for alkylation of chlorins dimethylamino groups by methyl iodide. 0.1 ml of iodomethane was added to a solution of 5-50 mg of starting chlorin (18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28) СH 3 ], -1.964 br.s (I-NH), -2.20/-2.24* br.s (III-NH). …”

Section: Chlorin E 6 Amides Aminomethylationmentioning

confidence: 99%

“…The tertiary amino groups quaternization were used for the formation of cationic substituent. This approach was used in the case of synthetic porphyrins [19][20][21][22][23][24][25] as well as in the case of natural porphyrins. [26][27][28][29] We have previously developed the method of aminomethylation of chlorin e 6 derivatives vinyl group by action of bis(N,N-dimethylamino)methane.…”

Section: Introductionmentioning

confidence: 99%