Synthesis, biodistribution and antitumor activity of hematoporphyrin–platinum(II) conjugates

Kim, Yeong-Sang; Song, Rita; Kim, Dong Hyun; Jun, Mira; Sohn, Youn Soo

doi:10.1016/s0968-0896(03)00029-4

Cited by 54 publications

(24 citation statements)

References 31 publications

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“…Cancer cells absorb the drug in question, which is delivered to the tumor via the bloodstream. [7] A number of chemotherapeutic drugs including doxorubicin (DOX), [8][9][10][11][12][13] cisplatin, [8] oxaliplatin derivatives, [7] vincristine, [10] platinum(II) complexes, [14] and organometallic ruthenium(II) complexes [15] have been evaluated in combination with PDT against several human tumor cell lines. [5] Significant effort has been recently devoted to combining this modality with other anticancer therapeutic methods.…”

Section: Introductionmentioning

confidence: 99%

“…[6] There are generally three approaches for dual PDT and chemotherapy: sequential administration of a photosensitizer and an anticancer drug, use of their covalent and noncovalent conjugates, and co-encapsulation of these agents in a polymeric nanocarrier. [7] A number of chemotherapeutic drugs including doxorubicin (DOX), [8][9][10][11][12][13] cisplatin, [8] oxaliplatin derivatives, [7] vincristine, [10] platinum(II) complexes, [14] and organometallic ruthenium(II) complexes [15] have been evaluated in combination with PDT against several human tumor cell lines. Remarkably, the results of these studies showed enhanced anticancer efficacy at lower drug doses, and in some cases, tumor drug resistance was even overcome.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and in vitro Anticancer Activity of Zinc(II) Phthalocyanines Conjugated with Coumarin Derivatives for Dual Photodynamic and Chemotherapy

et al. 2014

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The combination of photodynamic therapy and chemotherapy is a promising strategy to overcome growing problems in contemporary medicine, such as low therapeutic efficacy and drug resistance. Four zinc(II) phthalocyanine-coumarin conjugates were synthesized and characterized. In these complexes, zinc(II) phthalocyanine was used as the photosensitizing unit, and a coumarin derivative was selected as the cytostatic moiety; the two components were linked via a tri(ethylene glycol) chain. These conjugates exhibit high photocytotoxicity against HepG2 human hepatocarcinoma cells, with low IC50 values in the range of 0.014-0.044 μM. The high photodynamic activities of these conjugates are in accordance with their low aggregation tendency and high cellular uptake. One of these conjugates exhibits high photocytotoxicity and significantly higher chemocytotoxicity. The results clearly show that the two antitumor components in these conjugates work in a cooperative fashion. As shown by confocal microscopy, the conjugates can localize in the mitochondria and lysosomes, and one of the conjugates can also localize in the cell nuclei.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro Anticancer Activity of Zinc(II) Phthalocyanines Conjugated with Coumarin Derivatives for Dual Photodynamic and Chemotherapy

et al. 2014

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“…For example, brominated hematoporphyrin derivative 169 was converted to the corresponding PEGylated compounds 170a-170f by treatment with a stoichiometric excess of a methyl-capped PEG (Scheme 51) [153,154]. Concomittantly, the propionic acid side chains were also derivatized with PEG chains.…”

Section: Porphyrins Pegylated At Their β-Positionsmentioning

confidence: 99%

“…Concomittantly, the propionic acid side chains were also derivatized with PEG chains. After hydrolysis of the propionic ester side chains, platinum-conjugates were prepared and evaluated for their antitumor phototoxicty and cytotoxicity [153,154]. The PEGylated derivatives were amenable to aqueous work-up and purified by alumina chromatography.…”

Section: Porphyrins Pegylated At Their β-Positionsmentioning

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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“…Também tem sido utilizada a funcionalização dos grupos carboxílicos para a obtenção de derivados. 43,44 Além de apresentar baixa solubilidade, a Pp IX tem baixa absortividade molar na janela terapêutica (600-800 nm). Por isso, as pesquisas para a obtenção de derivados buscam melhorias aumentando a absortividade na janela terapêutica.…”

Section: -Fotossensibilizadoresunclassified

Síntese, caracterização e fotoatividade de fotossensibilizadores derivados de protoporfirina IX e de clorofilina

Fernandes¹

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4.1.2.4-Caracterização estrutural 4.1.3-Funcionalização de protoporfirina IX nas carboxilas em 13 e 3 4.1.3.1-Caracterização estrutural 4.1.4-Derivatização do sal de sódio cupro clorofilina (Cu 2+-clorofilina) 4.1.4.1-Desmetalação de Cu 2+-clorofilina 4.1.4.2-Obtenção de derivados amino-amida de clorofilina 4.2-Propriedades físicas e fotofísicas 4.2.1-Derivados de protoporfirina IX. 4.2.1.1-Espectros UV-visível e coeficientes de absorção Molar () 4.2.1.2-Espectro de fluorescência e rendimento quântico 4.2.1.3-Estudo fotólise de relâmpago a laser 4.2.1.4-Emissão de oxigênio singlete 4.2.1.5-Determinação dos agregados dos derivados de protoporfirina IX obtidos pela Rota III. 4.2.1.6-Coeficiente de partição 1-octanol/água 4.2.1.7-Incorporação em lipossomo em função do pH 4.2.2-Propriedades físicas e fotofísicas dos derivados de clorofilina 4.2.2.1-Espectros no visível e coeficientes de extinção molar () 4.2.2.2-Espectro de fluorescência e rendimento quântico 4.2.2.3-Geração e rendimento quântico de oxigênio singlete 4.2.2.4-Determinação da formação de estados agregados para os derivados de clorofilina 4.2.2.5-Coeficiente de partição 1-octanol/água 4.3-Determinação da atividade fotodinâmica 4.3.1-Derivados de protoporfirina IX 4.3.1.1-Taxa de incorporação 4.3.1.2-Toxicidade e fotocitoxicidade 4.3.2-Derivados de clorofilina. 4.3.2.1-Taxa de incorporação (lipossomo, célula e mitocôndria) 4.3.2.2-Toxicidade e fotocitotoxicidade 4.4-Citolocalização em células Hela 5-CONCLUSÕES 6-REFERÊNCIAS BIBLIOGRÁFICAS 7-APÊNDICES Micrografia transmitida (painel A), de fluorescência de PpNpNI (painel B), Rodamina 123 (painel C) e sobreposição de PpNpNI e Rodamina 123 (painel D) Lista de Esquemas 1 Diagrama cronológico do desenvolvimento da TFD. Diagrama de Jablonski simplificado e mecanismos de ação em TFD. Mecanismos Tipo I e Tipo II de fotossensibilização, sendo: Fs o fotossensibilizador no estado fundamental, 1 Fs* primeiro estado excito singleto e 3 Fs* primeiro estado tripleto e CIS cruzamento intersistema. 3 Processos fotoinduzidos que podem ocorrer após excitação eletrônica do Fs. 4 Rota biossintética da protoporfirina IX a partir do ácido α-aminolevulínico. 5 Macrocíclicos aromático, porfirínico e seus derivados (clorínicos e bacterioclorínicos). 6 Representação das formas de agregação: (a) face a face; (b) entre laterais; (c) faces laterais; (d) entre faces paralelas deslocadas. 7 Fatores que afetam o equilíbrio entre agregado e monômero. 8 Excitação eletrônica para porfirinas monoméricas (a) e agregadas de forma linear (b) e paralelas (c).

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Synthesis, biodistribution and antitumor activity of hematoporphyrin–platinum(II) conjugates

Cited by 54 publications

References 31 publications

Synthesis and in vitro Anticancer Activity of Zinc(II) Phthalocyanines Conjugated with Coumarin Derivatives for Dual Photodynamic and Chemotherapy

Synthesis and in vitro Anticancer Activity of Zinc(II) Phthalocyanines Conjugated with Coumarin Derivatives for Dual Photodynamic and Chemotherapy

Modifications of Porphyrins and Hydroporphyrins for their Solubilization in Aqueous Media

Síntese, caracterização e fotoatividade de fotossensibilizadores derivados de protoporfirina IX e de clorofilina

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