BSA/DNA binding behavior and the photophysicochemical properties of novel water soluble zinc(II)phthalocyanines directly substituted with piperazine groups
In the current research, two novel zinc(II) phthalocyanines (ZnPcs) ( 1 and 2 ) directly connecting with 4-(4-methylpiperazin-1-yl)phenyl groups have been synthesized through the Suzuki–Miyaura coupling reaction. These ZnPcs 1 and 2 were converted to their water-soluble derivatives ( 1Q and 2Q ) by...
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| Veröffentlicht in: | Journal of biological inorganic chemistry 2021-06, Vol.26 (4), p.455-465 |
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| container_title | Journal of biological inorganic chemistry |
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| creator | Khezami, Khaoula Harmandar, Kevser Bağda, Esra Bağda, Efkan Şahin, Gamze Karakodak, Nurşen Durmuş, Mahmut |
| description | In the current research, two novel zinc(II) phthalocyanines (ZnPcs) (
1
and
2
) directly connecting with 4-(4-methylpiperazin-1-yl)phenyl groups have been synthesized through the Suzuki–Miyaura coupling reaction. These ZnPcs
1
and
2
were converted to their water-soluble derivatives (
1Q
and
2Q
) by quaternization. The photochemical and photophysical properties were determined in DMSO for the non-ionic zinc(II) phthalocyanines (
1
and
2
) and in both DMSO and aqueous solutions for the quaternized cationic derivatives (
1Q
and
2Q
) to establish their photosensitizer capabilities in photodynamic therapy (PDT). The spectrofluorometric and spectrophotometric techniques were employed for the determination of interaction between water-soluble ZnPcs (
1Q
and
2Q
) and BSA or ct-DNA. The binding constants of these compounds to BSA were found in the order of 10
8
M
−1
. The binding constant of the ct-DNA interaction with
2Q
(1.09 × 10
5
M
−1
) was found higher than
1Q
(6.87 × 10
4
M
−1
). The thermodynamic constants were determined for both
1Q
and
2Q
. The endothermic and spontaneous nature of interaction was observed with ct-DNA. Besides, the thermal denaturation and viscosity studies proved the non-intercalative mode of binding for both compounds to ct-DNA.
Graphic abstract |
| doi_str_mv | 10.1007/s00775-021-01868-6 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2522389498</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2522389498</sourcerecordid><originalsourceid>FETCH-LOGICAL-c375t-3501556f252a393b9f602abe6c67eb0d7cf00167f9411c5364d2d76c61db4c533</originalsourceid><addsrcrecordid>eNp9kc1u1DAUhS0EokPhBVggS2zaRah_4jhZDqXASBUsgLVlOzcTVxk72E6r4VX6srhMC1IXbHxl3e-ca9-D0GtK3lFC5FkqhxQVYbQitG3aqnmCVrTmrKKcyadoRbq6q1om5BF6kdIVIYQLKp6jI867uu46uUK377-tzz58WWPjfO_8FhsY9bULEWvf4zwCnseQwzzuk7PBjrBzVk94jmGGmB0kHAbswzVM-EZniDiFaTET4F_O25PN5nQe86inYPfaO1_w3kWwedrjtJiUXV4y9PjG5RHPrljqogO8jWGZ00v0bNBTglf39Rj9-Hjx_fxzdfn10-Z8fVlZLkWuuCBUiGZggmnecdMNDWHaQGMbCYb00g6E0EYOXU2pFbype9bL0qW9qcudH6OTg2_51c8FUlY7lyxMk_YQlqSKMeNt2WVb0LeP0KuwRF9eV6ia8loy0RWKHSgbQ0oRBjVHt9NxryhRd9GpQ3SqRKf-RKeaInpzb72YHfR_JQ9ZFYAfgFRafgvx3-z_2P4GgASm4A</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2541347259</pqid></control><display><type>article</type><title>BSA/DNA binding behavior and the photophysicochemical properties of novel water soluble zinc(II)phthalocyanines directly substituted with piperazine groups</title><source>Springer Nature - Complete Springer Journals</source><creator>Khezami, Khaoula ; Harmandar, Kevser ; Bağda, Esra ; Bağda, Efkan ; Şahin, Gamze ; Karakodak, Nurşen ; Durmuş, Mahmut</creator><creatorcontrib>Khezami, Khaoula ; Harmandar, Kevser ; Bağda, Esra ; Bağda, Efkan ; Şahin, Gamze ; Karakodak, Nurşen ; Durmuş, Mahmut</creatorcontrib><description>In the current research, two novel zinc(II) phthalocyanines (ZnPcs) (
1
and
2
) directly connecting with 4-(4-methylpiperazin-1-yl)phenyl groups have been synthesized through the Suzuki–Miyaura coupling reaction. These ZnPcs
1
and
2
were converted to their water-soluble derivatives (
1Q
and
2Q
) by quaternization. The photochemical and photophysical properties were determined in DMSO for the non-ionic zinc(II) phthalocyanines (
1
and
2
) and in both DMSO and aqueous solutions for the quaternized cationic derivatives (
1Q
and
2Q
) to establish their photosensitizer capabilities in photodynamic therapy (PDT). The spectrofluorometric and spectrophotometric techniques were employed for the determination of interaction between water-soluble ZnPcs (
1Q
and
2Q
) and BSA or ct-DNA. The binding constants of these compounds to BSA were found in the order of 10
8
M
−1
. The binding constant of the ct-DNA interaction with
2Q
(1.09 × 10
5
M
−1
) was found higher than
1Q
(6.87 × 10
4
M
−1
). The thermodynamic constants were determined for both
1Q
and
2Q
. The endothermic and spontaneous nature of interaction was observed with ct-DNA. Besides, the thermal denaturation and viscosity studies proved the non-intercalative mode of binding for both compounds to ct-DNA.
Graphic abstract</description><identifier>ISSN: 0949-8257</identifier><identifier>EISSN: 1432-1327</identifier><identifier>DOI: 10.1007/s00775-021-01868-6</identifier><identifier>PMID: 33944997</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Biochemistry ; Biomedical and Life Sciences ; Deoxyribonucleic acid ; DNA ; Inorganic chemistry ; Life Sciences ; Microbiology ; Original Paper ; Photodynamic therapy ; Piperazine ; Spectrophotometry ; Thermal denaturation</subject><ispartof>Journal of biological inorganic chemistry, 2021-06, Vol.26 (4), p.455-465</ispartof><rights>Society for Biological Inorganic Chemistry (SBIC) 2021</rights><rights>Society for Biological Inorganic Chemistry (SBIC) 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c375t-3501556f252a393b9f602abe6c67eb0d7cf00167f9411c5364d2d76c61db4c533</citedby><cites>FETCH-LOGICAL-c375t-3501556f252a393b9f602abe6c67eb0d7cf00167f9411c5364d2d76c61db4c533</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00775-021-01868-6$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00775-021-01868-6$$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/33944997$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Khezami, Khaoula</creatorcontrib><creatorcontrib>Harmandar, Kevser</creatorcontrib><creatorcontrib>Bağda, Esra</creatorcontrib><creatorcontrib>Bağda, Efkan</creatorcontrib><creatorcontrib>Şahin, Gamze</creatorcontrib><creatorcontrib>Karakodak, Nurşen</creatorcontrib><creatorcontrib>Durmuş, Mahmut</creatorcontrib><title>BSA/DNA binding behavior and the photophysicochemical properties of novel water soluble zinc(II)phthalocyanines directly substituted with piperazine groups</title><title>Journal of biological inorganic chemistry</title><addtitle>J Biol Inorg Chem</addtitle><addtitle>J Biol Inorg Chem</addtitle><description>In the current research, two novel zinc(II) phthalocyanines (ZnPcs) (
1
and
2
) directly connecting with 4-(4-methylpiperazin-1-yl)phenyl groups have been synthesized through the Suzuki–Miyaura coupling reaction. These ZnPcs
1
and
2
were converted to their water-soluble derivatives (
1Q
and
2Q
) by quaternization. The photochemical and photophysical properties were determined in DMSO for the non-ionic zinc(II) phthalocyanines (
1
and
2
) and in both DMSO and aqueous solutions for the quaternized cationic derivatives (
1Q
and
2Q
) to establish their photosensitizer capabilities in photodynamic therapy (PDT). The spectrofluorometric and spectrophotometric techniques were employed for the determination of interaction between water-soluble ZnPcs (
1Q
and
2Q
) and BSA or ct-DNA. The binding constants of these compounds to BSA were found in the order of 10
8
M
−1
. The binding constant of the ct-DNA interaction with
2Q
(1.09 × 10
5
M
−1
) was found higher than
1Q
(6.87 × 10
4
M
−1
). The thermodynamic constants were determined for both
1Q
and
2Q
. The endothermic and spontaneous nature of interaction was observed with ct-DNA. Besides, the thermal denaturation and viscosity studies proved the non-intercalative mode of binding for both compounds to ct-DNA.
Graphic abstract</description><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>Inorganic chemistry</subject><subject>Life Sciences</subject><subject>Microbiology</subject><subject>Original Paper</subject><subject>Photodynamic therapy</subject><subject>Piperazine</subject><subject>Spectrophotometry</subject><subject>Thermal denaturation</subject><issn>0949-8257</issn><issn>1432-1327</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kc1u1DAUhS0EokPhBVggS2zaRah_4jhZDqXASBUsgLVlOzcTVxk72E6r4VX6srhMC1IXbHxl3e-ca9-D0GtK3lFC5FkqhxQVYbQitG3aqnmCVrTmrKKcyadoRbq6q1om5BF6kdIVIYQLKp6jI867uu46uUK377-tzz58WWPjfO_8FhsY9bULEWvf4zwCnseQwzzuk7PBjrBzVk94jmGGmB0kHAbswzVM-EZniDiFaTET4F_O25PN5nQe86inYPfaO1_w3kWwedrjtJiUXV4y9PjG5RHPrljqogO8jWGZ00v0bNBTglf39Rj9-Hjx_fxzdfn10-Z8fVlZLkWuuCBUiGZggmnecdMNDWHaQGMbCYb00g6E0EYOXU2pFbype9bL0qW9qcudH6OTg2_51c8FUlY7lyxMk_YQlqSKMeNt2WVb0LeP0KuwRF9eV6ia8loy0RWKHSgbQ0oRBjVHt9NxryhRd9GpQ3SqRKf-RKeaInpzb72YHfR_JQ9ZFYAfgFRafgvx3-z_2P4GgASm4A</recordid><startdate>20210601</startdate><enddate>20210601</enddate><creator>Khezami, Khaoula</creator><creator>Harmandar, Kevser</creator><creator>Bağda, Esra</creator><creator>Bağda, Efkan</creator><creator>Şahin, Gamze</creator><creator>Karakodak, Nurşen</creator><creator>Durmuş, Mahmut</creator><general>Springer International Publishing</general><general>Springer Nature B.V</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20210601</creationdate><title>BSA/DNA binding behavior and the photophysicochemical properties of novel water soluble zinc(II)phthalocyanines directly substituted with piperazine groups</title><author>Khezami, Khaoula ; Harmandar, Kevser ; Bağda, Esra ; Bağda, Efkan ; Şahin, Gamze ; Karakodak, Nurşen ; Durmuş, Mahmut</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c375t-3501556f252a393b9f602abe6c67eb0d7cf00167f9411c5364d2d76c61db4c533</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>Inorganic chemistry</topic><topic>Life Sciences</topic><topic>Microbiology</topic><topic>Original Paper</topic><topic>Photodynamic therapy</topic><topic>Piperazine</topic><topic>Spectrophotometry</topic><topic>Thermal denaturation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Khezami, Khaoula</creatorcontrib><creatorcontrib>Harmandar, Kevser</creatorcontrib><creatorcontrib>Bağda, Esra</creatorcontrib><creatorcontrib>Bağda, Efkan</creatorcontrib><creatorcontrib>Şahin, Gamze</creatorcontrib><creatorcontrib>Karakodak, Nurşen</creatorcontrib><creatorcontrib>Durmuş, Mahmut</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of biological inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Khezami, Khaoula</au><au>Harmandar, Kevser</au><au>Bağda, Esra</au><au>Bağda, Efkan</au><au>Şahin, Gamze</au><au>Karakodak, Nurşen</au><au>Durmuş, Mahmut</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>BSA/DNA binding behavior and the photophysicochemical properties of novel water soluble zinc(II)phthalocyanines directly substituted with piperazine groups</atitle><jtitle>Journal of biological inorganic chemistry</jtitle><stitle>J Biol Inorg Chem</stitle><addtitle>J Biol Inorg Chem</addtitle><date>2021-06-01</date><risdate>2021</risdate><volume>26</volume><issue>4</issue><spage>455</spage><epage>465</epage><pages>455-465</pages><issn>0949-8257</issn><eissn>1432-1327</eissn><abstract>In the current research, two novel zinc(II) phthalocyanines (ZnPcs) (
1
and
2
) directly connecting with 4-(4-methylpiperazin-1-yl)phenyl groups have been synthesized through the Suzuki–Miyaura coupling reaction. These ZnPcs
1
and
2
were converted to their water-soluble derivatives (
1Q
and
2Q
) by quaternization. The photochemical and photophysical properties were determined in DMSO for the non-ionic zinc(II) phthalocyanines (
1
and
2
) and in both DMSO and aqueous solutions for the quaternized cationic derivatives (
1Q
and
2Q
) to establish their photosensitizer capabilities in photodynamic therapy (PDT). The spectrofluorometric and spectrophotometric techniques were employed for the determination of interaction between water-soluble ZnPcs (
1Q
and
2Q
) and BSA or ct-DNA. The binding constants of these compounds to BSA were found in the order of 10
8
M
−1
. The binding constant of the ct-DNA interaction with
2Q
(1.09 × 10
5
M
−1
) was found higher than
1Q
(6.87 × 10
4
M
−1
). The thermodynamic constants were determined for both
1Q
and
2Q
. The endothermic and spontaneous nature of interaction was observed with ct-DNA. Besides, the thermal denaturation and viscosity studies proved the non-intercalative mode of binding for both compounds to ct-DNA.
Graphic abstract</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><pmid>33944997</pmid><doi>10.1007/s00775-021-01868-6</doi><tpages>11</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0949-8257 |
| ispartof | Journal of biological inorganic chemistry, 2021-06, Vol.26 (4), p.455-465 |
| issn | 0949-8257 1432-1327 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2522389498 |
| source | Springer Nature - Complete Springer Journals |
| subjects | Biochemistry Biomedical and Life Sciences Deoxyribonucleic acid DNA Inorganic chemistry Life Sciences Microbiology Original Paper Photodynamic therapy Piperazine Spectrophotometry Thermal denaturation |
| title | BSA/DNA binding behavior and the photophysicochemical properties of novel water soluble zinc(II)phthalocyanines directly substituted with piperazine groups |
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