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Phthalocyanines and Tetrapyrazinoporphyrazines with Two Cationic Donuts: High Photodynamic Activity as a Result of Rigid Spatial Arrangement of Peripheral Substituents
B. Ghazal, M. Machacek, MA. Shalaby, V. Novakova, P. Zimcik, S. Makhseed,
Jazyk angličtina Země Spojené státy americké
Typ dokumentu časopisecké články
- MeSH
- fotochemoterapie MeSH
- fotosenzibilizující látky chemická syntéza chemie farmakologie MeSH
- indoly chemická syntéza chemie farmakologie MeSH
- krystalografie rentgenová MeSH
- léky antitumorózní - screeningové testy MeSH
- lidé MeSH
- lyzozomy metabolismus MeSH
- molekulární konformace MeSH
- nádorové buněčné linie MeSH
- nekróza MeSH
- porfyriny chemická syntéza chemie farmakologie MeSH
- pyrazoly chemická syntéza chemie farmakologie MeSH
- triazoly chemická syntéza chemie farmakologie MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
High photodynamic activity was observed for hexadeca-cationic zinc, magnesium, and metal-free phthalocyanines (Pcs) and tetrapyrazinoporphyrazines with EC50 values as low as 5 nM (MCF-7 cells) for the best compound; this activity was several times better than that of clinically established photosensitizers verteporfin, temoporfin, S3AlOHPc, or protoporphyrin IX. This lead compound was characterized by low dark toxicity (TC50 = 369 μM), high efficiency against other cell lines (HCT 116 and HeLa), and possible activation by light above 680 nm. The excellent photodynamic activity resulted from the rigid spatial arrangement of the quaternized triazole moieties above and below the Pc core, as confirmed by X-ray crystallography. The triazole moieties thus formed two "cationic donuts" that protected the hydrophobic core against aggregation in water. The lysosomes were found to be the site of subcellular localization and were consequently the primary targets of photodynamic injury, resulting in predominantly necrotic cell death.
Citace poskytuje Crossref.org
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- $a Ghazal, Basma $u Department of Chemistry, Kuwait University , P.O. Box 5969, Safat, 13060, Kuwait.
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- $a High photodynamic activity was observed for hexadeca-cationic zinc, magnesium, and metal-free phthalocyanines (Pcs) and tetrapyrazinoporphyrazines with EC50 values as low as 5 nM (MCF-7 cells) for the best compound; this activity was several times better than that of clinically established photosensitizers verteporfin, temoporfin, S3AlOHPc, or protoporphyrin IX. This lead compound was characterized by low dark toxicity (TC50 = 369 μM), high efficiency against other cell lines (HCT 116 and HeLa), and possible activation by light above 680 nm. The excellent photodynamic activity resulted from the rigid spatial arrangement of the quaternized triazole moieties above and below the Pc core, as confirmed by X-ray crystallography. The triazole moieties thus formed two "cationic donuts" that protected the hydrophobic core against aggregation in water. The lysosomes were found to be the site of subcellular localization and were consequently the primary targets of photodynamic injury, resulting in predominantly necrotic cell death.
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