Synthesis, characterization and cytotoxic activity of 5,10,15,20‐tetrakis[4‐(triorganostannyloxy)phenyl]porphyrins

doi:10.1002/AOC.2971

Paper

Synthesis, characterization and cytotoxic activity of 5,10,15,20‐tetrakis[4‐(triorganostannyloxy)phenyl]porphyrins

Published Mar 1, 2013 · Laijin Tian, Xian-yi Cao, Yanxiang Zhao

Applied Organometallic Chemistry

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Abstract

5,10,15,20-Tetrakis[4-(triorganostannyloxy)phenyl]porphyrins, (R3SnO)4TPP [2, R = Cy (a), Ph (b), PhC(CH3)2CH2 (c)], have been synthesized by the condensation of 4-(triorganostannyloxy)benzaldehyde, 4-(R3SnO)C6H4CHO (1), with pyrrole in the presence of BF3 followed by oxidation by p-chloranil and characterized by means of elemental analysis, IR, UV–visible and NMR (1H, 13C and 119Sn) spectra. The results of X-ray single-crystal diffraction show that 1a and 1b possess a trans-C3SnO2 trigonal bipyramidal geometry with the axial positions occupied by the phenolate oxygen and formyl group oxygen of an adjacent molecule and form a one-dimensional zigzag chain. In 2a, the macrocyclic core of the porphyrin is coplanar and each tin atom possesses a distorted tetrahedral geometry. These compounds (1 and 2) have potent in vitro cytotoxic activity against two human tumor cell lines – CoLo205 and MCF-7 – and the activity decreases in the order Ph > Cy > PhC(CH3)2CH2 for the R group bound to tin. Copyright © 2013 John Wiley & Sons, Ltd.

In Vitro Study

Study Snapshot

5,10,15,20-tetrakis[4-(triorganostannyloxy)phenyl]porphyrins show potent cytotoxic activity against human tumor cell lines CoLo205 and MCF-7, with activity decreasing from Ph to Cy to PhC(CH3)2CH2

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis, characterization and cytotoxic activity of 5,10,15,20‐tetrakis[4‐(triorganostannyloxy)phenyl]porphyrins

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References

Porous metalloporphyrinic frameworks constructed from metal 5,10,15,20-tetrakis(3,5-biscarboxylphenyl)porphyrin for highly efficient and selective catalytic oxidation of alkylbenzenes.

ZJU-18, a porous metalloporphyrinic framework, exhibits highly efficient and selective catalytic oxidation of ethylbenzene to acetophenone with a turnover number of 8076 after 48 hours.

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Manganese-porphyrin-catalyzed epoxidation and C-H hydroxylation in water/methanol solutions produce enantioselective epoxides and alcohols with enantiomeric excess up to 68% and 57%, respectively.

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The multi-porphyrin cascade light-harvesting antenna 1 efficiently absorbs visible light up to 700 nm, with high efficiency and low rate constants.

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Chromium porphyrin arrays show half-metallic behavior and can be used as flexible, half-metal spintronic devices for future information technology applications.

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Long-wavelength porphyrin-based compounds show promise in photodynamic therapy and tumor imaging, with potential for Theranostics.

Citations

Investigation of protonation effects on the electronic and structural properties of halogenated sulfonated porphyrins

Protonation of halogenated sulfonated porphyrins in extremely acid environments may enhance their photodynamic efficiency and reduce aggregation, making them potential candidates for efficient photosensitizers.