Parietin: an efficient photo-screening pigment in vivo with good photosensitizing and photodynamic antibacterial effects in vitro
The photophysical, photoinduced pro-oxidant and antibacterial properties in vitro of the natural occurring parietin (PTN; 1,8-dihydroxy-3-methoxy-6-methyl-9,10-anthraquinone) were evaluated. PTN was extracted from the lichen identified as Teloschistes flavicans (Sw.) Norm. (Telochistaceae). Results...
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| Veröffentlicht in: | Photochemical & photobiological sciences 2017-02, Vol.16 (2), p.201-210 |
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| creator | Comini, Laura R. Morán Vieyra, F. Eduardo Mignone, Ricardo A. Páez, Paulina L. Laura Mugas, M. Konigheim, Brenda S. Cabrera, José L. Núñez Montoya, Susana C. Borsarelli, Claudio D. |
| description | The photophysical, photoinduced pro-oxidant and antibacterial properties
in vitro
of the natural occurring parietin (PTN; 1,8-dihydroxy-3-methoxy-6-methyl-9,10-anthraquinone) were evaluated. PTN was extracted from the lichen identified as
Teloschistes flavicans
(Sw.) Norm. (Telochistaceae). Results indicate that in chloroform solution, PTN presents spectroscopic features corresponding to an excited-state intramolecular proton-transfer (ESIPT) state with partial keto–enol tautomerization. In argon-saturated solutions, the singlet excited state is poorly fluorescent (
F
F
= 0.03), decaying by efficient intersystem crossing to an excited triplet state
3
PTN*, as detected by laser-flash photolysis experiments. In the presence of triplet molecular oxygen, the
3
PTN* was fully quenched producing singlet molecular oxygen (
1
O
2
) with a quantum yield of 0.69. In addition, in buffer solutions, PTN has the ability to also generate a superoxide radical anion (O
2
?
-
) in a human leukocyte model and its production was enhanced under UVA-Vis irradiation. Finally, the
in vitro
antibacterial capability of PTN in the dark and under UVA-Vis illumination was compared in microbial cultures of both Gram positive and negative bacteria. As a result, PTN showed promising photo-induced antibacterial activity through the efficient photosensitized generation of both
1
O
2
and O
2
?
-
species. Thus, we have demonstrated that PTN, an efficient photo-screening pigment in lichens, is also a good photosensitizer in solution with promising applications in antibacterial photodynamic therapy. |
| doi_str_mv | 10.1039/c6pp00334f |
| format | Article |
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in vitro
of the natural occurring parietin (PTN; 1,8-dihydroxy-3-methoxy-6-methyl-9,10-anthraquinone) were evaluated. PTN was extracted from the lichen identified as
Teloschistes flavicans
(Sw.) Norm. (Telochistaceae). Results indicate that in chloroform solution, PTN presents spectroscopic features corresponding to an excited-state intramolecular proton-transfer (ESIPT) state with partial keto–enol tautomerization. In argon-saturated solutions, the singlet excited state is poorly fluorescent (
F
F
= 0.03), decaying by efficient intersystem crossing to an excited triplet state
3
PTN*, as detected by laser-flash photolysis experiments. In the presence of triplet molecular oxygen, the
3
PTN* was fully quenched producing singlet molecular oxygen (
1
O
2
) with a quantum yield of 0.69. In addition, in buffer solutions, PTN has the ability to also generate a superoxide radical anion (O
2
?
-
) in a human leukocyte model and its production was enhanced under UVA-Vis irradiation. Finally, the
in vitro
antibacterial capability of PTN in the dark and under UVA-Vis illumination was compared in microbial cultures of both Gram positive and negative bacteria. As a result, PTN showed promising photo-induced antibacterial activity through the efficient photosensitized generation of both
1
O
2
and O
2
?
-
species. Thus, we have demonstrated that PTN, an efficient photo-screening pigment in lichens, is also a good photosensitizer in solution with promising applications in antibacterial photodynamic therapy.</description><identifier>ISSN: 1474-905X</identifier><identifier>EISSN: 1474-9092</identifier><identifier>DOI: 10.1039/c6pp00334f</identifier><identifier>PMID: 27976779</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Animals ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Biochemistry ; Biomaterials ; Cell Survival - drug effects ; Cercopithecus aethiops ; Chemistry ; Emodin - analogs & derivatives ; Emodin - chemistry ; Emodin - isolation & purification ; Emodin - pharmacology ; Gram-Negative Bacteria - drug effects ; Gram-Negative Bacteria - radiation effects ; Gram-Positive Bacteria - drug effects ; Gram-Positive Bacteria - radiation effects ; Humans ; Leukocytes - drug effects ; Leukocytes - metabolism ; Leukocytes - radiation effects ; Lichens - chemistry ; Lichens - metabolism ; Light ; Microbial Sensitivity Tests ; Photosensitizing Agents - chemistry ; Photosensitizing Agents - isolation & purification ; Photosensitizing Agents - pharmacology ; Physical Chemistry ; Plant Sciences ; Singlet Oxygen - chemistry ; Singlet Oxygen - metabolism ; Spectrophotometry, Ultraviolet ; Superoxides - chemistry ; Superoxides - metabolism ; Teloschistes flavicans ; Ultraviolet Rays ; Vero Cells</subject><ispartof>Photochemical & photobiological sciences, 2017-02, Vol.16 (2), p.201-210</ispartof><rights>The Royal Society of Chemistry and Owner Societies 2017</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c434t-2d28c749447bce0dd3c437ba464b88d0ae961c3fec9bb8ae78e9a7883bd29bae3</citedby><cites>FETCH-LOGICAL-c434t-2d28c749447bce0dd3c437ba464b88d0ae961c3fec9bb8ae78e9a7883bd29bae3</cites><orcidid>0000-0002-2030-0890</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1039/c6pp00334f$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1039/c6pp00334f$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27976779$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Comini, Laura R.</creatorcontrib><creatorcontrib>Morán Vieyra, F. Eduardo</creatorcontrib><creatorcontrib>Mignone, Ricardo A.</creatorcontrib><creatorcontrib>Páez, Paulina L.</creatorcontrib><creatorcontrib>Laura Mugas, M.</creatorcontrib><creatorcontrib>Konigheim, Brenda S.</creatorcontrib><creatorcontrib>Cabrera, José L.</creatorcontrib><creatorcontrib>Núñez Montoya, Susana C.</creatorcontrib><creatorcontrib>Borsarelli, Claudio D.</creatorcontrib><title>Parietin: an efficient photo-screening pigment in vivo with good photosensitizing and photodynamic antibacterial effects in vitro</title><title>Photochemical & photobiological sciences</title><addtitle>Photochem Photobiol Sci</addtitle><addtitle>Photochem Photobiol Sci</addtitle><description>The photophysical, photoinduced pro-oxidant and antibacterial properties
in vitro
of the natural occurring parietin (PTN; 1,8-dihydroxy-3-methoxy-6-methyl-9,10-anthraquinone) were evaluated. PTN was extracted from the lichen identified as
Teloschistes flavicans
(Sw.) Norm. (Telochistaceae). Results indicate that in chloroform solution, PTN presents spectroscopic features corresponding to an excited-state intramolecular proton-transfer (ESIPT) state with partial keto–enol tautomerization. In argon-saturated solutions, the singlet excited state is poorly fluorescent (
F
F
= 0.03), decaying by efficient intersystem crossing to an excited triplet state
3
PTN*, as detected by laser-flash photolysis experiments. In the presence of triplet molecular oxygen, the
3
PTN* was fully quenched producing singlet molecular oxygen (
1
O
2
) with a quantum yield of 0.69. In addition, in buffer solutions, PTN has the ability to also generate a superoxide radical anion (O
2
?
-
) in a human leukocyte model and its production was enhanced under UVA-Vis irradiation. Finally, the
in vitro
antibacterial capability of PTN in the dark and under UVA-Vis illumination was compared in microbial cultures of both Gram positive and negative bacteria. As a result, PTN showed promising photo-induced antibacterial activity through the efficient photosensitized generation of both
1
O
2
and O
2
?
-
species. Thus, we have demonstrated that PTN, an efficient photo-screening pigment in lichens, is also a good photosensitizer in solution with promising applications in antibacterial photodynamic therapy.</description><subject>Animals</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Biochemistry</subject><subject>Biomaterials</subject><subject>Cell Survival - drug effects</subject><subject>Cercopithecus aethiops</subject><subject>Chemistry</subject><subject>Emodin - analogs & derivatives</subject><subject>Emodin - chemistry</subject><subject>Emodin - isolation & purification</subject><subject>Emodin - pharmacology</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Gram-Negative Bacteria - radiation effects</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Gram-Positive Bacteria - radiation effects</subject><subject>Humans</subject><subject>Leukocytes - drug effects</subject><subject>Leukocytes - metabolism</subject><subject>Leukocytes - radiation effects</subject><subject>Lichens - chemistry</subject><subject>Lichens - metabolism</subject><subject>Light</subject><subject>Microbial Sensitivity Tests</subject><subject>Photosensitizing Agents - chemistry</subject><subject>Photosensitizing Agents - isolation & purification</subject><subject>Photosensitizing Agents - pharmacology</subject><subject>Physical Chemistry</subject><subject>Plant Sciences</subject><subject>Singlet Oxygen - chemistry</subject><subject>Singlet Oxygen - metabolism</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Superoxides - chemistry</subject><subject>Superoxides - metabolism</subject><subject>Teloschistes flavicans</subject><subject>Ultraviolet Rays</subject><subject>Vero Cells</subject><issn>1474-905X</issn><issn>1474-9092</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkU9LwzAYh4MoOqcXP4D0KEo1bbIm8SbDfyDoQcFbSdK3W2RNapJN5s1vbkfnvHjw9IZfHp4X3h9CRxk-zzARF7poW4wJofUWGmSU0VRgkW9v3qPXPbQfwhvG2YgWbBft5UywgjExQF9P0huIxl4m0iZQ10YbsDFppy66NGgPYI2dJK2ZNKvc2GRhFi75MHGaTJyrejKADSaazxUq7TqsllY2RndBNErqCN7I2WoH6Bh6U_TuAO3UchbgcD2H6OXm-nl8lz483t6Prx5STQmNaV7lXDMqKGVKA64q0uVMSVpQxXmFJYgi06RzC6W4BMZBSMY5UVUulAQyRCe9t_XufQ4hlo0JGmYzacHNQ5lxlnNS8Kz4BzrKC04JwR162qPauxA81GXrTSP9ssxwuWqn_G2ng4_X3rlqoNqgP3V0wFkPhO7LTsCXb27ubXeWv3TfcrGdCA</recordid><startdate>20170201</startdate><enddate>20170201</enddate><creator>Comini, Laura R.</creator><creator>Morán Vieyra, F. Eduardo</creator><creator>Mignone, Ricardo A.</creator><creator>Páez, Paulina L.</creator><creator>Laura Mugas, M.</creator><creator>Konigheim, Brenda S.</creator><creator>Cabrera, José L.</creator><creator>Núñez Montoya, Susana C.</creator><creator>Borsarelli, Claudio D.</creator><general>Springer International Publishing</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QL</scope><scope>7QO</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-2030-0890</orcidid></search><sort><creationdate>20170201</creationdate><title>Parietin: an efficient photo-screening pigment in vivo with good photosensitizing and photodynamic antibacterial effects in vitro</title><author>Comini, Laura R. ; Morán Vieyra, F. Eduardo ; Mignone, Ricardo A. ; Páez, Paulina L. ; Laura Mugas, M. ; Konigheim, Brenda S. ; Cabrera, José L. ; Núñez Montoya, Susana C. ; Borsarelli, Claudio D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c434t-2d28c749447bce0dd3c437ba464b88d0ae961c3fec9bb8ae78e9a7883bd29bae3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Animals</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Biochemistry</topic><topic>Biomaterials</topic><topic>Cell Survival - drug effects</topic><topic>Cercopithecus aethiops</topic><topic>Chemistry</topic><topic>Emodin - analogs & derivatives</topic><topic>Emodin - chemistry</topic><topic>Emodin - isolation & purification</topic><topic>Emodin - pharmacology</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Gram-Negative Bacteria - radiation effects</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>Gram-Positive Bacteria - radiation effects</topic><topic>Humans</topic><topic>Leukocytes - drug effects</topic><topic>Leukocytes - metabolism</topic><topic>Leukocytes - radiation effects</topic><topic>Lichens - chemistry</topic><topic>Lichens - metabolism</topic><topic>Light</topic><topic>Microbial Sensitivity Tests</topic><topic>Photosensitizing Agents - chemistry</topic><topic>Photosensitizing Agents - isolation & purification</topic><topic>Photosensitizing Agents - pharmacology</topic><topic>Physical Chemistry</topic><topic>Plant Sciences</topic><topic>Singlet Oxygen - chemistry</topic><topic>Singlet Oxygen - metabolism</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Superoxides - chemistry</topic><topic>Superoxides - metabolism</topic><topic>Teloschistes flavicans</topic><topic>Ultraviolet Rays</topic><topic>Vero Cells</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Comini, Laura R.</creatorcontrib><creatorcontrib>Morán Vieyra, F. Eduardo</creatorcontrib><creatorcontrib>Mignone, Ricardo A.</creatorcontrib><creatorcontrib>Páez, Paulina L.</creatorcontrib><creatorcontrib>Laura Mugas, M.</creatorcontrib><creatorcontrib>Konigheim, Brenda S.</creatorcontrib><creatorcontrib>Cabrera, José L.</creatorcontrib><creatorcontrib>Núñez Montoya, Susana C.</creatorcontrib><creatorcontrib>Borsarelli, Claudio D.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Photochemical & photobiological sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Comini, Laura R.</au><au>Morán Vieyra, F. Eduardo</au><au>Mignone, Ricardo A.</au><au>Páez, Paulina L.</au><au>Laura Mugas, M.</au><au>Konigheim, Brenda S.</au><au>Cabrera, José L.</au><au>Núñez Montoya, Susana C.</au><au>Borsarelli, Claudio D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Parietin: an efficient photo-screening pigment in vivo with good photosensitizing and photodynamic antibacterial effects in vitro</atitle><jtitle>Photochemical & photobiological sciences</jtitle><stitle>Photochem Photobiol Sci</stitle><addtitle>Photochem Photobiol Sci</addtitle><date>2017-02-01</date><risdate>2017</risdate><volume>16</volume><issue>2</issue><spage>201</spage><epage>210</epage><pages>201-210</pages><issn>1474-905X</issn><eissn>1474-9092</eissn><abstract>The photophysical, photoinduced pro-oxidant and antibacterial properties
in vitro
of the natural occurring parietin (PTN; 1,8-dihydroxy-3-methoxy-6-methyl-9,10-anthraquinone) were evaluated. PTN was extracted from the lichen identified as
Teloschistes flavicans
(Sw.) Norm. (Telochistaceae). Results indicate that in chloroform solution, PTN presents spectroscopic features corresponding to an excited-state intramolecular proton-transfer (ESIPT) state with partial keto–enol tautomerization. In argon-saturated solutions, the singlet excited state is poorly fluorescent (
F
F
= 0.03), decaying by efficient intersystem crossing to an excited triplet state
3
PTN*, as detected by laser-flash photolysis experiments. In the presence of triplet molecular oxygen, the
3
PTN* was fully quenched producing singlet molecular oxygen (
1
O
2
) with a quantum yield of 0.69. In addition, in buffer solutions, PTN has the ability to also generate a superoxide radical anion (O
2
?
-
) in a human leukocyte model and its production was enhanced under UVA-Vis irradiation. Finally, the
in vitro
antibacterial capability of PTN in the dark and under UVA-Vis illumination was compared in microbial cultures of both Gram positive and negative bacteria. As a result, PTN showed promising photo-induced antibacterial activity through the efficient photosensitized generation of both
1
O
2
and O
2
?
-
species. Thus, we have demonstrated that PTN, an efficient photo-screening pigment in lichens, is also a good photosensitizer in solution with promising applications in antibacterial photodynamic therapy.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><pmid>27976779</pmid><doi>10.1039/c6pp00334f</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-2030-0890</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1474-905X |
| ispartof | Photochemical & photobiological sciences, 2017-02, Vol.16 (2), p.201-210 |
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| source | MEDLINE; SpringerLink Journals |
| subjects | Animals Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Biochemistry Biomaterials Cell Survival - drug effects Cercopithecus aethiops Chemistry Emodin - analogs & derivatives Emodin - chemistry Emodin - isolation & purification Emodin - pharmacology Gram-Negative Bacteria - drug effects Gram-Negative Bacteria - radiation effects Gram-Positive Bacteria - drug effects Gram-Positive Bacteria - radiation effects Humans Leukocytes - drug effects Leukocytes - metabolism Leukocytes - radiation effects Lichens - chemistry Lichens - metabolism Light Microbial Sensitivity Tests Photosensitizing Agents - chemistry Photosensitizing Agents - isolation & purification Photosensitizing Agents - pharmacology Physical Chemistry Plant Sciences Singlet Oxygen - chemistry Singlet Oxygen - metabolism Spectrophotometry, Ultraviolet Superoxides - chemistry Superoxides - metabolism Teloschistes flavicans Ultraviolet Rays Vero Cells |
| title | Parietin: an efficient photo-screening pigment in vivo with good photosensitizing and photodynamic antibacterial effects in vitro |
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