Synthesis, characterization and urease inhibition, in vitro anticancer and antileishmanial studies of Ni(II) complexes with N,N,N′-trisubstituted thioureas
A series of N , N , N ′-trisubstituted thioureas ( 1–12 ) and their Ni(II) complexes ( 1a–12a ) were synthesized and characterized by multinuclear ( 1 H and 13 C) NMR, FT-IR spectroscopy and LC–MS techniques in combination with elemental analysis. The crystal structures of both ligands and Ni(II) ch...
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| Veröffentlicht in: | Journal of biological inorganic chemistry 2015-04, Vol.20 (3), p.541-554 |
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| container_title | Journal of biological inorganic chemistry |
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| creator | Rauf, Muhammad Khawar Yaseen, Samad Badshah, Amin Zaib, Sumera Arshad, Raffia Imtiaz-ud-Din Tahir, Muhammad Nawaz Iqbal, Jamshed |
| description | A series of
N
,
N
,
N
′-trisubstituted thioureas (
1–12
) and their Ni(II) complexes (
1a–12a
) were synthesized and characterized by multinuclear (
1
H and
13
C) NMR, FT-IR spectroscopy and LC–MS techniques in combination with elemental analysis. The crystal structures of both ligands and Ni(II) chelates of type Ni(L-
O
,
S
)
2
were determined by single crystal X-ray diffraction analysis. All the complexes were adopted to have square planar geometry, where the
N
,
N
,
N
′-trisubstituted thioureas showed bidentate mode of coordination at nickel centre through oxygen and sulfur atoms. The synthesized complexes were screened for potential inhibitors of Jack bean urease. Compounds
1a
and
3a
were observed as most potent inhibitors of urease exhibiting IC
50
values of 1.17 ± 0.12 and 1.19 ± 0.41 µM, respectively. Cytotoxicity assay on lung carcinoma (H-157) and kidney fibroblast (BHK-21) cell showed that compounds were significant anticancer agents. Additionally, the complexes were tested against
Leishmania major
and found to be potent antileishmanial agents. |
| doi_str_mv | 10.1007/s00775-015-1239-5 |
| format | Article |
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N
,
N
,
N
′-trisubstituted thioureas (
1–12
) and their Ni(II) complexes (
1a–12a
) were synthesized and characterized by multinuclear (
1
H and
13
C) NMR, FT-IR spectroscopy and LC–MS techniques in combination with elemental analysis. The crystal structures of both ligands and Ni(II) chelates of type Ni(L-
O
,
S
)
2
were determined by single crystal X-ray diffraction analysis. All the complexes were adopted to have square planar geometry, where the
N
,
N
,
N
′-trisubstituted thioureas showed bidentate mode of coordination at nickel centre through oxygen and sulfur atoms. The synthesized complexes were screened for potential inhibitors of Jack bean urease. Compounds
1a
and
3a
were observed as most potent inhibitors of urease exhibiting IC
50
values of 1.17 ± 0.12 and 1.19 ± 0.41 µM, respectively. Cytotoxicity assay on lung carcinoma (H-157) and kidney fibroblast (BHK-21) cell showed that compounds were significant anticancer agents. Additionally, the complexes were tested against
Leishmania major
and found to be potent antileishmanial agents.</description><identifier>ISSN: 0949-8257</identifier><identifier>EISSN: 1432-1327</identifier><identifier>DOI: 10.1007/s00775-015-1239-5</identifier><identifier>PMID: 25604966</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Animals ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biochemistry ; Biological Assay ; Biomedical and Life Sciences ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cercopithecus aethiops ; Coordination Complexes - chemical synthesis ; Coordination Complexes - chemistry ; Coordination Complexes - pharmacology ; Crystallography, X-Ray ; Humans ; Leishmania - drug effects ; Leishmania major ; Life Sciences ; Microbiology ; Nickel - chemistry ; Original Paper ; Thiourea - chemistry ; Trypanocidal Agents - chemical synthesis ; Trypanocidal Agents - chemistry ; Trypanocidal Agents - pharmacology ; Urease - antagonists & inhibitors ; Vero Cells</subject><ispartof>Journal of biological inorganic chemistry, 2015-04, Vol.20 (3), p.541-554</ispartof><rights>SBIC 2015</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c447t-c815972a98efd9426888b3eee1368917a110cac002b21e93874fee452d183c7c3</citedby><cites>FETCH-LOGICAL-c447t-c815972a98efd9426888b3eee1368917a110cac002b21e93874fee452d183c7c3</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/s00775-015-1239-5$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00775-015-1239-5$$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/25604966$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rauf, Muhammad Khawar</creatorcontrib><creatorcontrib>Yaseen, Samad</creatorcontrib><creatorcontrib>Badshah, Amin</creatorcontrib><creatorcontrib>Zaib, Sumera</creatorcontrib><creatorcontrib>Arshad, Raffia</creatorcontrib><creatorcontrib>Imtiaz-ud-Din</creatorcontrib><creatorcontrib>Tahir, Muhammad Nawaz</creatorcontrib><creatorcontrib>Iqbal, Jamshed</creatorcontrib><title>Synthesis, characterization and urease inhibition, in vitro anticancer and antileishmanial studies of Ni(II) complexes with N,N,N′-trisubstituted thioureas</title><title>Journal of biological inorganic chemistry</title><addtitle>J Biol Inorg Chem</addtitle><addtitle>J Biol Inorg Chem</addtitle><description>A series of
N
,
N
,
N
′-trisubstituted thioureas (
1–12
) and their Ni(II) complexes (
1a–12a
) were synthesized and characterized by multinuclear (
1
H and
13
C) NMR, FT-IR spectroscopy and LC–MS techniques in combination with elemental analysis. The crystal structures of both ligands and Ni(II) chelates of type Ni(L-
O
,
S
)
2
were determined by single crystal X-ray diffraction analysis. All the complexes were adopted to have square planar geometry, where the
N
,
N
,
N
′-trisubstituted thioureas showed bidentate mode of coordination at nickel centre through oxygen and sulfur atoms. The synthesized complexes were screened for potential inhibitors of Jack bean urease. Compounds
1a
and
3a
were observed as most potent inhibitors of urease exhibiting IC
50
values of 1.17 ± 0.12 and 1.19 ± 0.41 µM, respectively. Cytotoxicity assay on lung carcinoma (H-157) and kidney fibroblast (BHK-21) cell showed that compounds were significant anticancer agents. Additionally, the complexes were tested against
Leishmania major
and found to be potent antileishmanial agents.</description><subject>Animals</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biochemistry</subject><subject>Biological Assay</subject><subject>Biomedical and Life Sciences</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cercopithecus aethiops</subject><subject>Coordination Complexes - chemical synthesis</subject><subject>Coordination Complexes - chemistry</subject><subject>Coordination Complexes - pharmacology</subject><subject>Crystallography, X-Ray</subject><subject>Humans</subject><subject>Leishmania - drug effects</subject><subject>Leishmania major</subject><subject>Life Sciences</subject><subject>Microbiology</subject><subject>Nickel - chemistry</subject><subject>Original Paper</subject><subject>Thiourea - chemistry</subject><subject>Trypanocidal Agents - chemical synthesis</subject><subject>Trypanocidal Agents - chemistry</subject><subject>Trypanocidal Agents - pharmacology</subject><subject>Urease - antagonists & inhibitors</subject><subject>Vero Cells</subject><issn>0949-8257</issn><issn>1432-1327</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkUtuFDEQhi1ERIbAAdggL4M0Bj-77SWKIIwUJQtgbbnd1bSjfgy2GwgrLpJLcCROgjsTWCJkqeyq-uq3VD9Czxh9ySitX6USakUoU4RxYYh6gDZMCk6Y4PVDtKFGGqK5qo_R45SuKaVCMfUIHXNVUWmqaoNu399MuYcU0hb73kXnM8Tw3eUwT9hNLV4iuAQ4TH1owlrdljf-EnKcSz8H7yYP8Q5d0wFC6kc3BTfglJc2QMJzhy_D6W73Avt53A_wrdS-htzjy205v378JDmGtDQph7xkaHHuw3z37xN01LkhwdP7-wR9fPvmw9k7cnF1vjt7fUG8lHUmXjNlau6Mhq41klda60YAABOVNqx2jFHvPKW84QyM0LXsAKTiLdPC116coNOD7j7OnxdI2Y4heRgGN8G8JMsqTaWSVOr_QCtTlBVdUXZAfZxTitDZfQyjizeWUbsaaA8G2mKgXQ20qsw8v5dfmhHavxN_HCsAPwCptKZPEO112dVUtvMP1d9oe6kd</recordid><startdate>20150401</startdate><enddate>20150401</enddate><creator>Rauf, Muhammad Khawar</creator><creator>Yaseen, Samad</creator><creator>Badshah, Amin</creator><creator>Zaib, Sumera</creator><creator>Arshad, Raffia</creator><creator>Imtiaz-ud-Din</creator><creator>Tahir, Muhammad Nawaz</creator><creator>Iqbal, Jamshed</creator><general>Springer Berlin Heidelberg</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>M7N</scope></search><sort><creationdate>20150401</creationdate><title>Synthesis, characterization and urease inhibition, in vitro anticancer and antileishmanial studies of Ni(II) complexes with N,N,N′-trisubstituted thioureas</title><author>Rauf, Muhammad Khawar ; Yaseen, Samad ; Badshah, Amin ; Zaib, Sumera ; Arshad, Raffia ; Imtiaz-ud-Din ; Tahir, Muhammad Nawaz ; Iqbal, Jamshed</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c447t-c815972a98efd9426888b3eee1368917a110cac002b21e93874fee452d183c7c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biochemistry</topic><topic>Biological Assay</topic><topic>Biomedical and Life Sciences</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cercopithecus aethiops</topic><topic>Coordination Complexes - chemical synthesis</topic><topic>Coordination Complexes - chemistry</topic><topic>Coordination Complexes - pharmacology</topic><topic>Crystallography, X-Ray</topic><topic>Humans</topic><topic>Leishmania - drug effects</topic><topic>Leishmania major</topic><topic>Life Sciences</topic><topic>Microbiology</topic><topic>Nickel - chemistry</topic><topic>Original Paper</topic><topic>Thiourea - chemistry</topic><topic>Trypanocidal Agents - chemical synthesis</topic><topic>Trypanocidal Agents - chemistry</topic><topic>Trypanocidal Agents - pharmacology</topic><topic>Urease - antagonists & inhibitors</topic><topic>Vero Cells</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rauf, Muhammad Khawar</creatorcontrib><creatorcontrib>Yaseen, Samad</creatorcontrib><creatorcontrib>Badshah, Amin</creatorcontrib><creatorcontrib>Zaib, Sumera</creatorcontrib><creatorcontrib>Arshad, Raffia</creatorcontrib><creatorcontrib>Imtiaz-ud-Din</creatorcontrib><creatorcontrib>Tahir, Muhammad Nawaz</creatorcontrib><creatorcontrib>Iqbal, Jamshed</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>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><jtitle>Journal of biological inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rauf, Muhammad Khawar</au><au>Yaseen, Samad</au><au>Badshah, Amin</au><au>Zaib, Sumera</au><au>Arshad, Raffia</au><au>Imtiaz-ud-Din</au><au>Tahir, Muhammad Nawaz</au><au>Iqbal, Jamshed</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization and urease inhibition, in vitro anticancer and antileishmanial studies of Ni(II) complexes with N,N,N′-trisubstituted thioureas</atitle><jtitle>Journal of biological inorganic chemistry</jtitle><stitle>J Biol Inorg Chem</stitle><addtitle>J Biol Inorg Chem</addtitle><date>2015-04-01</date><risdate>2015</risdate><volume>20</volume><issue>3</issue><spage>541</spage><epage>554</epage><pages>541-554</pages><issn>0949-8257</issn><eissn>1432-1327</eissn><abstract>A series of
N
,
N
,
N
′-trisubstituted thioureas (
1–12
) and their Ni(II) complexes (
1a–12a
) were synthesized and characterized by multinuclear (
1
H and
13
C) NMR, FT-IR spectroscopy and LC–MS techniques in combination with elemental analysis. The crystal structures of both ligands and Ni(II) chelates of type Ni(L-
O
,
S
)
2
were determined by single crystal X-ray diffraction analysis. All the complexes were adopted to have square planar geometry, where the
N
,
N
,
N
′-trisubstituted thioureas showed bidentate mode of coordination at nickel centre through oxygen and sulfur atoms. The synthesized complexes were screened for potential inhibitors of Jack bean urease. Compounds
1a
and
3a
were observed as most potent inhibitors of urease exhibiting IC
50
values of 1.17 ± 0.12 and 1.19 ± 0.41 µM, respectively. Cytotoxicity assay on lung carcinoma (H-157) and kidney fibroblast (BHK-21) cell showed that compounds were significant anticancer agents. Additionally, the complexes were tested against
Leishmania major
and found to be potent antileishmanial agents.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><pmid>25604966</pmid><doi>10.1007/s00775-015-1239-5</doi><tpages>14</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0949-8257 |
| ispartof | Journal of biological inorganic chemistry, 2015-04, Vol.20 (3), p.541-554 |
| issn | 0949-8257 1432-1327 |
| language | eng |
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| source | MEDLINE; Springer Nature - Complete Springer Journals |
| subjects | Animals Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biochemistry Biological Assay Biomedical and Life Sciences Cell Line, Tumor Cell Proliferation - drug effects Cercopithecus aethiops Coordination Complexes - chemical synthesis Coordination Complexes - chemistry Coordination Complexes - pharmacology Crystallography, X-Ray Humans Leishmania - drug effects Leishmania major Life Sciences Microbiology Nickel - chemistry Original Paper Thiourea - chemistry Trypanocidal Agents - chemical synthesis Trypanocidal Agents - chemistry Trypanocidal Agents - pharmacology Urease - antagonists & inhibitors Vero Cells |
| title | Synthesis, characterization and urease inhibition, in vitro anticancer and antileishmanial studies of Ni(II) complexes with N,N,N′-trisubstituted thioureas |
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