title: Phthalocyanine derivatives possessing 2-(morpholin-4-yl)ethoxy groups as potential agents for photodynamic therapy.
abstract: Three 2-(morpholin-4-yl)ethoxy substituted phthalocyanines were synthesized and characterized. Phthalocyanine derivatives revealed moderate to high quantum yields of singlet oxygen production depending on the solvent applied (e.g., in DMF ranging from 0.25 to 0.53). Their photosensitizing potential for photodynamic therapy was investigated in an in vitro model using cancer cell lines. Biological test results were found particularly encouraging for the zinc(II) phthalocyanine derivative possessing two 2-(morpholin-4-yl)ethoxy substituents in nonperipheral positions. Cells irradiated for 20 min at 2 mW/cm(2) revealed the lowest IC50 value at 0.25 μM for prostate cell line (PC3), whereas 1.47 μM was observed for human malignant melanoma (A375) cells. The cytotoxic activity in nonirradiated cells of novel phthalocyanine was found to be very low. Moreover, the cellular uptake, localization, cell cycle, apoptosis through an ELISA assay, and immunochemistry method were investigated in LNCaP cells. Our results showed that the tested photosensitizer possesses very interesting biological activity, depending on experimental conditions.
authors.affiliation: Department of Toxicology, Poznan University of Medical Sciences , Dojazd 30, 60-631 Poznan, Poland.
authors.forename: Malgorzata
authors.initials: M
authors.lastname: Kucinska
authors.forename: Paulina
authors.initials: P
authors.lastname: Skupin-Mrugalska
authors.forename: Wojciech
authors.initials: W
authors.lastname: Szczolko
authors.forename: Lukasz
authors.initials: L
authors.lastname: Sobotta
authors.forename: Mateusz
authors.initials: M
authors.lastname: Sciepura
authors.forename: Ewa
authors.initials: E
authors.lastname: Tykarska
authors.forename: Marcin
authors.initials: M
authors.lastname: Wierzchowski
authors.forename: Anna
authors.initials: A
authors.lastname: Teubert
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Fedoruk-Wyszomirska
authors.forename: Eliza
authors.initials: E
authors.lastname: Wyszko
authors.forename: Maria
authors.initials: M
authors.lastname: Gdaniec
authors.forename: Mariusz
authors.initials: M
authors.lastname: Kaczmarek
authors.forename: Tomasz
authors.initials: T
authors.lastname: Goslinski
authors.forename: Jadwiga
authors.initials: J
authors.lastname: Mielcarek
authors.forename: Marek
authors.initials: M
authors.lastname: Murias
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D002453:Cell Cycle / Q000187:drug effects; D018360:Crystallography, X-Ray; D004797:Enzyme-Linked Immunosorbent Assay; D006801:Humans; D007211:Indoles / Q000737:chemistry / Q000494:pharmacology*; D054833:Isoindoles; D008027:Light; D008297:Male; D008545:Melanoma / Q000188:drug therapy* / Q000473:pathology; D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry / Q000494:pharmacology*; D009942:Organometallic Compounds / Q000737:chemistry / Q000494:pharmacology*; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000737:chemistry / Q000494:pharmacology*; D011471:Prostatic Neoplasms / Q000188:drug therapy* / Q000473:pathology; D026082:Singlet Oxygen; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D007211:Indoles; D054833:Isoindoles; D009025:Morpholines; D009942:Organometallic Compounds; D017319:Photosensitizing Agents; D026082:Singlet Oxygen; C013647:phthalocyanine