Amphiphilic zinc phthalocyanine dendrimers by the Click Chemistry approach

Hahn, Uwe; Torres, Tomás

doi:10.1142/s1088424611003161

Cited by 15 publications

(3 citation statements)

References 8 publications

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“…On the other hand, it is important to synthesis water soluble phthalocyanine compounds for biomedical applications [25,26]. In the literature, different water soluble dendritic phthalocyanine compounds have been synthesized and their photophysical [27,28,29], spectroscopic [30,31], electron transfer processes [32,33], electrical and CO2 sensing properties [34] have been investigated. Therefore, synthesis of new water soluble dendritic phthalocyanine compounds and investigation of their anticancer activities could be worthwhile.…”

Section: Dendrimers Are Highly Branched Macromoleculesmentioning

confidence: 99%

Effect of New Water-Soluble Dendritic Phthalocyanines on Human Colorectal and Liver Cancer Cell Lines

Yabaş

Sülü²,

Özgür³

et al. 2017

SDÜ Fen Bil Enst Der

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Human hepatocellular carcinoma (HepG2) cells and colorectal adenocarcinoma (DLD-1) cells were treated with the synthesized water soluble phthalocyanine derivatives to understand the effect of the compounds both on colorectal and liver cancer cells. The compounds inhibited cell proliferation and displayed cytotoxic effect on these cancer cell lines however; the effect of the compounds on healthy control fibroblast cell line was comparatively lower. The compounds can be employed for cancer treatment as anticancer agents. Yeni Suda Çözünür Dendritik Ftalosiyaninlerin İnsan Kolorektal ve Karaciğer KanserHücre Hatları Üzerine Etkisi Anahtar KelimelerDendrimer, Antikanser aktivitesi, Karaciğer kanseri, Kolorektal kanser Özet: İnsan hepatoselüler karsinoma (HepG2) hücreleri ve kolorektal adenokarsinoma (DLD-1) hücreleri, bileşiklerin hem kolorektal hemde karaciğer kanseri hücrelerindeki etkisini anlamak için sentezlenen suda çözünür ftalosiyanin türevleriyle etkileştirildi. Bileşikler hücre proliferasyonunu inhibe etti ve bu kanser hücre dizileri üzerinde sitotoksik etki gösterdi; buna karşın bileşiklerin sağlıklı kontrol fibroblast hücre hattı üzerindeki etkisi nispeten daha düşüktü. Bu bileşikler kanser tedavisinde antikanser ajanlar olarak kullanılabilir.

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Section: Dendrimers Are Highly Branched Macromoleculesmentioning

confidence: 99%

Effect of New Water-Soluble Dendritic Phthalocyanines on Human Colorectal and Liver Cancer Cell Lines

Yabaş

Sülü²,

Özgür³

et al. 2017

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“…[1][2][3] Their application in the synthesis and processing of self-organizing and self-assembling materials, however, has been limited to the synthesis of molecular building blocks and the modication of self-assembled monolayers 4 and Langmuir-Blodgett lms. 5 CuAAC is a particularly powerful reaction for the construction of complex structures through covalent bond formation such as the attachment of large dendrons to a rotaxane core, 6 the synthesis of oligomeric phthalocyanines, [7][8][9] and the attachment of dyes to polymers and carbon nanotubes. 10 The 1,2,3triazole rings that result from the CuAAC may also benet self-organization and electronic properties of the generated adducts due to their strong dipole and aromatic character.…”

Section: Introductionmentioning

confidence: 99%

“…2,3,7,8,12,13,17,18-octakis(pent-4-yn-1-ylthio)-5,10,15,20-tetraazaporphyrin (7a) (770 mg, 70%): 1 H NMR (300 MHz, CDCl 3 , d):2,3,7,8,12,13,17,18-octakis(undeca-10-yn-1-ylthio)-5,10,15,…”

mentioning

confidence: 99%

Cross-linking of discotic tetraazaporphyrin dyes in 2 and 3 dimensions by “click” chemistry

et al. 2013

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An intrinsic shortcoming of self-organizing materials is their susceptibility to structural changes by mechanical forces and exposure to chemicals and radiation. Cross-linking of the molecules in the desired supramolecular structure is a generally applicable pathway to structurally more stable materials but is difficult to apply to self-organizing materials because the introduction of cross-linkable groups affects their self-organization and the process of cross-linking may alter the supramolecular structure of the 10 preceding phase. Reported here are the synthesis, thermal properties, and cross-linking of octaalkylthio substituted tetraazaporphyrins that contain either eight terminal azide groups or eight terminal acetylene groups. Synthesis of these compounds requires the preparation of the azide and alkyne containing sidechains and their reaction with 1,2-dicyanoethylene-1,2-dithiolate to the corresponding maleodinitrile intermediates. All maleodinitriles are successfully converted to tetraazaporphyrins by the established Mg 15 templated cyclotetramerization in typical yields of 60-70%. Thermal properties of the metal-free and copper(II) metallated tetraazaporphyrins were studied by thermal gravimetric analysis, polarized optical microscopy, differential scanning calorimetry, and variable temperature powder X-ray diffraction measurements. Azide substituted tetraazaporphyrins with trimethylene and hexamethylene spacers as well as acetylene derivatives with with trimethylene spacers unexpectedly display columnar mesophases over 20 ranges of temperature from 30 ºC to 110 ºC. A thermally activated cross-linking of a hexagonal columnar mesophase by cycloaddition at 65 ºC is demonstrated for a 1:1 mixture of azide and acetylene derivatives. At this temperatures the reaction progresses for up to 48 hours but renders the mesophase insoluble and stable to above 200 ºC. The structure of the mesophase is surprisingly little affected by the cross-coupling process that reaches a conversion of 60% of all azide and acetylene groups based on IR measurements. 25 Conversion of up to 80% of azide and acetylene groups is reached by copper catalysed cross-linking of a 1:1 mixture in solution to generate insoluble polymers. A similar degree of conversion is achieved by copper catalysed cross-linking of a 1:1 mixture as Langmuir film after 3 hours. However, transfer of intact cross-linked Langmuir films onto substrates was not successful.

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Polymer Complexes Based on Metal Chelate Monomers

Джардималиева

Uflyand

2018

Chemistry of Polymeric Metal Chelates

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Amphiphilic zinc phthalocyanine dendrimers by the Click Chemistry approach

Cited by 15 publications

References 8 publications

Effect of New Water-Soluble Dendritic Phthalocyanines on Human Colorectal and Liver Cancer Cell Lines

Effect of New Water-Soluble Dendritic Phthalocyanines on Human Colorectal and Liver Cancer Cell Lines

Cross-linking of discotic tetraazaporphyrin dyes in 2 and 3 dimensions by “click” chemistry

Polymer Complexes Based on Metal Chelate Monomers

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