Photophysical Properties and Photobiological Behavior of Amodiaquine, Primaquine and Chloroquine
This article describes the results of a coupled photophysical and photobiological study aimed at understanding the phototoxicity mechanism of the antimalarial drugs amodiaquine (AQ), primaquine (PQ) and chloroquine (CQ). Photophysical experiments were carried out in aqueous solutions by steady‐state...
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| Veröffentlicht in: | Photochemistry and photobiology 2007-11, Vol.83 (6), p.1415-1427 |
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| creator | Viola, Giampietro Salvador, Alessia Cecconet, Laura Basso, Giuseppe Vedaldi, Daniela Dall'Acqua, Francesco Aloisi, Gian Gaetano Amelia, Matteo Barbafina, Arianna Latterini, Loredana Elisei, Fausto |
| description | This article describes the results of a coupled photophysical and photobiological study aimed at understanding the phototoxicity mechanism of the antimalarial drugs amodiaquine (AQ), primaquine (PQ) and chloroquine (CQ). Photophysical experiments were carried out in aqueous solutions by steady‐state and time‐resolved spectrometric techniques to obtain information on the different decay pathways of the excited states of the drugs and on the transient species formed upon laser irradiation. The results showed that all three drugs possess very low fluorescence quantum yields (10−2–10−4). Laser flash photolysis experiments proved the occurrence of photoionization processes leading to the formation of a radical cation in all three systems. In the case of AQ the lowest triplet state was also detected.
Together with the photophysical properties the photobiological properties of the antimalarial drugs were investigated under UV irradiation, on various biological targets through a series of in vitro assays. Phototoxicity on mouse 3T3 fibroblast and human keratinocyte cell lines NCTC‐2544 was detected for PQ and CQ but not for AQ. In particular, PQ‐ and CQ‐induced apoptosis was revealed by the externalization of phosphatidylserine. Furthermore, upon UV irradiation, the drugs caused significant variations of the mitochondrial potential (Δψmt) measured by flow cytometry. The photodamages produced by the drugs were also evaluated on proteins, lipids and DNA. The combined approaches were useful in understanding the mechanism of phototoxicity induced by these antimalarial drugs. |
| doi_str_mv | 10.1111/j.1751-1097.2007.00181.x |
| format | Article |
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Together with the photophysical properties the photobiological properties of the antimalarial drugs were investigated under UV irradiation, on various biological targets through a series of in vitro assays. Phototoxicity on mouse 3T3 fibroblast and human keratinocyte cell lines NCTC‐2544 was detected for PQ and CQ but not for AQ. In particular, PQ‐ and CQ‐induced apoptosis was revealed by the externalization of phosphatidylserine. Furthermore, upon UV irradiation, the drugs caused significant variations of the mitochondrial potential (Δψmt) measured by flow cytometry. The photodamages produced by the drugs were also evaluated on proteins, lipids and DNA. The combined approaches were useful in understanding the mechanism of phototoxicity induced by these antimalarial drugs.</description><identifier>ISSN: 0031-8655</identifier><identifier>EISSN: 1751-1097</identifier><identifier>DOI: 10.1111/j.1751-1097.2007.00181.x</identifier><identifier>PMID: 18028216</identifier><identifier>CODEN: PHCBAP</identifier><language>eng</language><publisher>Oxford, UK: Blackwell Publishing Ltd</publisher><subject>Amodiaquine - chemistry ; Amodiaquine - toxicity ; Animals ; Antimalarials ; Apoptosis ; Blindness ; Cell Line ; Cell Survival - drug effects ; Cell Survival - radiation effects ; Chloroquine - chemistry ; Chloroquine - toxicity ; DNA - genetics ; DNA Damage ; Drugs ; Free radicals ; Humans ; Lipid Peroxidation - drug effects ; Lipid Peroxidation - radiation effects ; Lysosomes - drug effects ; Lysosomes - radiation effects ; Mice ; Mitochondria - drug effects ; Mitochondria - radiation effects ; Molecular Structure ; Photobiology ; Photochemistry ; Primaquine - chemistry ; Primaquine - toxicity ; Reactive Oxygen Species - metabolism ; Salmon ; Spectrophotometry</subject><ispartof>Photochemistry and photobiology, 2007-11, Vol.83 (6), p.1415-1427</ispartof><rights>Copyright American Society for Photobiology Nov/Dec 2007</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4621-ab3026ca687d7390ffc31abcd769dea7ecd98d3dbb25271cd4245e0f403f28ec3</citedby><cites>FETCH-LOGICAL-c4621-ab3026ca687d7390ffc31abcd769dea7ecd98d3dbb25271cd4245e0f403f28ec3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fj.1751-1097.2007.00181.x$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fj.1751-1097.2007.00181.x$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18028216$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Viola, Giampietro</creatorcontrib><creatorcontrib>Salvador, Alessia</creatorcontrib><creatorcontrib>Cecconet, Laura</creatorcontrib><creatorcontrib>Basso, Giuseppe</creatorcontrib><creatorcontrib>Vedaldi, Daniela</creatorcontrib><creatorcontrib>Dall'Acqua, Francesco</creatorcontrib><creatorcontrib>Aloisi, Gian Gaetano</creatorcontrib><creatorcontrib>Amelia, Matteo</creatorcontrib><creatorcontrib>Barbafina, Arianna</creatorcontrib><creatorcontrib>Latterini, Loredana</creatorcontrib><creatorcontrib>Elisei, Fausto</creatorcontrib><title>Photophysical Properties and Photobiological Behavior of Amodiaquine, Primaquine and Chloroquine</title><title>Photochemistry and photobiology</title><addtitle>Photochem Photobiol</addtitle><description>This article describes the results of a coupled photophysical and photobiological study aimed at understanding the phototoxicity mechanism of the antimalarial drugs amodiaquine (AQ), primaquine (PQ) and chloroquine (CQ). Photophysical experiments were carried out in aqueous solutions by steady‐state and time‐resolved spectrometric techniques to obtain information on the different decay pathways of the excited states of the drugs and on the transient species formed upon laser irradiation. The results showed that all three drugs possess very low fluorescence quantum yields (10−2–10−4). Laser flash photolysis experiments proved the occurrence of photoionization processes leading to the formation of a radical cation in all three systems. In the case of AQ the lowest triplet state was also detected.
Together with the photophysical properties the photobiological properties of the antimalarial drugs were investigated under UV irradiation, on various biological targets through a series of in vitro assays. Phototoxicity on mouse 3T3 fibroblast and human keratinocyte cell lines NCTC‐2544 was detected for PQ and CQ but not for AQ. In particular, PQ‐ and CQ‐induced apoptosis was revealed by the externalization of phosphatidylserine. Furthermore, upon UV irradiation, the drugs caused significant variations of the mitochondrial potential (Δψmt) measured by flow cytometry. The photodamages produced by the drugs were also evaluated on proteins, lipids and DNA. The combined approaches were useful in understanding the mechanism of phototoxicity induced by these antimalarial drugs.</description><subject>Amodiaquine - chemistry</subject><subject>Amodiaquine - toxicity</subject><subject>Animals</subject><subject>Antimalarials</subject><subject>Apoptosis</subject><subject>Blindness</subject><subject>Cell Line</subject><subject>Cell Survival - drug effects</subject><subject>Cell Survival - radiation effects</subject><subject>Chloroquine - chemistry</subject><subject>Chloroquine - toxicity</subject><subject>DNA - genetics</subject><subject>DNA Damage</subject><subject>Drugs</subject><subject>Free radicals</subject><subject>Humans</subject><subject>Lipid Peroxidation - drug effects</subject><subject>Lipid Peroxidation - radiation effects</subject><subject>Lysosomes - drug effects</subject><subject>Lysosomes - radiation effects</subject><subject>Mice</subject><subject>Mitochondria - drug effects</subject><subject>Mitochondria - radiation effects</subject><subject>Molecular Structure</subject><subject>Photobiology</subject><subject>Photochemistry</subject><subject>Primaquine - chemistry</subject><subject>Primaquine - toxicity</subject><subject>Reactive Oxygen Species - 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Fausto</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photophysical Properties and Photobiological Behavior of Amodiaquine, Primaquine and Chloroquine</atitle><jtitle>Photochemistry and photobiology</jtitle><addtitle>Photochem Photobiol</addtitle><date>2007-11</date><risdate>2007</risdate><volume>83</volume><issue>6</issue><spage>1415</spage><epage>1427</epage><pages>1415-1427</pages><issn>0031-8655</issn><eissn>1751-1097</eissn><coden>PHCBAP</coden><abstract>This article describes the results of a coupled photophysical and photobiological study aimed at understanding the phototoxicity mechanism of the antimalarial drugs amodiaquine (AQ), primaquine (PQ) and chloroquine (CQ). Photophysical experiments were carried out in aqueous solutions by steady‐state and time‐resolved spectrometric techniques to obtain information on the different decay pathways of the excited states of the drugs and on the transient species formed upon laser irradiation. The results showed that all three drugs possess very low fluorescence quantum yields (10−2–10−4). Laser flash photolysis experiments proved the occurrence of photoionization processes leading to the formation of a radical cation in all three systems. In the case of AQ the lowest triplet state was also detected.
Together with the photophysical properties the photobiological properties of the antimalarial drugs were investigated under UV irradiation, on various biological targets through a series of in vitro assays. Phototoxicity on mouse 3T3 fibroblast and human keratinocyte cell lines NCTC‐2544 was detected for PQ and CQ but not for AQ. In particular, PQ‐ and CQ‐induced apoptosis was revealed by the externalization of phosphatidylserine. Furthermore, upon UV irradiation, the drugs caused significant variations of the mitochondrial potential (Δψmt) measured by flow cytometry. The photodamages produced by the drugs were also evaluated on proteins, lipids and DNA. The combined approaches were useful in understanding the mechanism of phototoxicity induced by these antimalarial drugs.</abstract><cop>Oxford, UK</cop><pub>Blackwell Publishing Ltd</pub><pmid>18028216</pmid><doi>10.1111/j.1751-1097.2007.00181.x</doi><tpages>13</tpages></addata></record> |
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| subjects | Amodiaquine - chemistry Amodiaquine - toxicity Animals Antimalarials Apoptosis Blindness Cell Line Cell Survival - drug effects Cell Survival - radiation effects Chloroquine - chemistry Chloroquine - toxicity DNA - genetics DNA Damage Drugs Free radicals Humans Lipid Peroxidation - drug effects Lipid Peroxidation - radiation effects Lysosomes - drug effects Lysosomes - radiation effects Mice Mitochondria - drug effects Mitochondria - radiation effects Molecular Structure Photobiology Photochemistry Primaquine - chemistry Primaquine - toxicity Reactive Oxygen Species - metabolism Salmon Spectrophotometry |
| title | Photophysical Properties and Photobiological Behavior of Amodiaquine, Primaquine and Chloroquine |
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