A detailed quantum chemical investigation on the hydrolysis mechanism of osmium() anticancer drug, (ImH)[-OsCl(DMSO)(Im)] (Os-NAMI-A; Im = imidazole)
Detailed hydrolysis mechanism of osmium( iii ) anticancer drug, (ImH)[ trans -OsCl 4 (DMSO)(Im)] (Os-NAMI-A; Im = imidazole, DMSO = dimethyl sulfoxide) has been investigated using density functional theory (DFT) in combination with CPCM solvation model. In the first hydrolysis step, faster aquation...
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| Veröffentlicht in: | New journal of chemistry 2021-03, Vol.45 (12), p.5682-5694 |
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| creator | Pradhan, Amit Kumar Shyam, Abhijit Mondal, Paritosh |
| description | Detailed hydrolysis mechanism of osmium(
iii
) anticancer drug, (ImH)[
trans
-OsCl
4
(DMSO)(Im)] (Os-NAMI-A; Im = imidazole, DMSO = dimethyl sulfoxide) has been investigated using density functional theory (DFT) in combination with CPCM solvation model. In the first hydrolysis step, faster aquation is observed in the case of DMSO hydrolysis from Os-NAMI-A in comparison to the chloro ligand having activation Gibbs free energy (Δ
G
aq
) value of 24.66 kcal mol
−1
, which is in good agreement with the experimental results. On the other hand, the second hydrolysis is mainly performed
via
the first chloro ligand hydrolysed Os-NAMI-A to form
cis
-[OsCl
2
(H
2
O)
2
(DMSO)(Im)]
+
(
P-2B
). However, the hydrolysis of
cis
-diaquated Os-NAMI-A [OsCl
3
(H
2
O)
2
(Im)] (
P-2A
) shows enhanced feasibility in the third hydrolysis step with the lowest activation Gibbs free energy (17.27 kcal mol
−1
) and the rate constant value is computed to be 1.34 s
−1
. Additionally, it is observed that hydrogen bonding plays an important role in stabilizing the intermediates and transition states. Furthermore, calculated net atomic charges based on natural population analysis show charge redistribution during hydrolysis reactions.
Detailed hydrolysis mechanism of osmium(
iii
) anticancer drug, (ImH)[
trans
-OsCl
4
(DMSO)(Im)] (Os-NAMI-A; Im = imidazole, DMSO = dimethyl sulfoxide) has been investigated using density functional theory (DFT) in combination with CPCM solvation model. |
| doi_str_mv | 10.1039/d1nj00783a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2506286321</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2506286321</sourcerecordid><originalsourceid>FETCH-LOGICAL-c281t-5e04eeab012a08c8ebb91a53e6cf25d7657b92c237003c4bf544bed79a4c08813</originalsourceid><addsrcrecordid>eNpFkU1Lw0AQhoMoWKsX78KCl0aM7kc-EQ-h9SPSNgf1JBI2m02zJZu0u4lQ_4f_160VhYEZhmfeYd6xrFMErxAk0XWBmiWEQUjonjVAxI-cCPto39TIdR3ouf6hdaS1YRAKfDSwvmJQ8I6Kmhdg3dOm6yVgFZeC0RqI5oPrTixoJ9oGmOgqDqpNodp6o4UGkrOKNkJL0Jag1VL0cmQDI2KmG8YVKFS_uASjRD7ab06qx_VoMntObdOw38Eo1c48niVOfAMSCW6BkKKgn23N7WProKS15ie_eWi93t-9jB-dafqQjOOpw3CIOsfj0OWc5hBhCkMW8jyPEPUI91mJvSLwvSCPMMMkgJAwNy891815EUTUZTAMERla5zvdlWrXvbk1W7a9aszKDHvQx6FP8Ja62FFMtVorXmYrJSRVmwzBbGt7NkHzpx_bYwOf7WCl2R_3_xbyDZRTfVs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2506286321</pqid></control><display><type>article</type><title>A detailed quantum chemical investigation on the hydrolysis mechanism of osmium() anticancer drug, (ImH)[-OsCl(DMSO)(Im)] (Os-NAMI-A; Im = imidazole)</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Pradhan, Amit Kumar ; Shyam, Abhijit ; Mondal, Paritosh</creator><creatorcontrib>Pradhan, Amit Kumar ; Shyam, Abhijit ; Mondal, Paritosh</creatorcontrib><description>Detailed hydrolysis mechanism of osmium(
iii
) anticancer drug, (ImH)[
trans
-OsCl
4
(DMSO)(Im)] (Os-NAMI-A; Im = imidazole, DMSO = dimethyl sulfoxide) has been investigated using density functional theory (DFT) in combination with CPCM solvation model. In the first hydrolysis step, faster aquation is observed in the case of DMSO hydrolysis from Os-NAMI-A in comparison to the chloro ligand having activation Gibbs free energy (Δ
G
aq
) value of 24.66 kcal mol
−1
, which is in good agreement with the experimental results. On the other hand, the second hydrolysis is mainly performed
via
the first chloro ligand hydrolysed Os-NAMI-A to form
cis
-[OsCl
2
(H
2
O)
2
(DMSO)(Im)]
+
(
P-2B
). However, the hydrolysis of
cis
-diaquated Os-NAMI-A [OsCl
3
(H
2
O)
2
(Im)] (
P-2A
) shows enhanced feasibility in the third hydrolysis step with the lowest activation Gibbs free energy (17.27 kcal mol
−1
) and the rate constant value is computed to be 1.34 s
−1
. Additionally, it is observed that hydrogen bonding plays an important role in stabilizing the intermediates and transition states. Furthermore, calculated net atomic charges based on natural population analysis show charge redistribution during hydrolysis reactions.
Detailed hydrolysis mechanism of osmium(
iii
) anticancer drug, (ImH)[
trans
-OsCl
4
(DMSO)(Im)] (Os-NAMI-A; Im = imidazole, DMSO = dimethyl sulfoxide) has been investigated using density functional theory (DFT) in combination with CPCM solvation model.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d1nj00783a</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Activation energy ; Cancer ; Cartesian coordinates ; Density functional theory ; Dimethyl sulfoxide ; Gibbs free energy ; Hydrogen bonding ; Hydrolysis ; Imidazole ; Ligands ; Osmium ; Quantum chemistry ; Solvation</subject><ispartof>New journal of chemistry, 2021-03, Vol.45 (12), p.5682-5694</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-5e04eeab012a08c8ebb91a53e6cf25d7657b92c237003c4bf544bed79a4c08813</citedby><cites>FETCH-LOGICAL-c281t-5e04eeab012a08c8ebb91a53e6cf25d7657b92c237003c4bf544bed79a4c08813</cites><orcidid>0000-0003-1089-1620</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27926,27927</link.rule.ids></links><search><creatorcontrib>Pradhan, Amit Kumar</creatorcontrib><creatorcontrib>Shyam, Abhijit</creatorcontrib><creatorcontrib>Mondal, Paritosh</creatorcontrib><title>A detailed quantum chemical investigation on the hydrolysis mechanism of osmium() anticancer drug, (ImH)[-OsCl(DMSO)(Im)] (Os-NAMI-A; Im = imidazole)</title><title>New journal of chemistry</title><description>Detailed hydrolysis mechanism of osmium(
iii
) anticancer drug, (ImH)[
trans
-OsCl
4
(DMSO)(Im)] (Os-NAMI-A; Im = imidazole, DMSO = dimethyl sulfoxide) has been investigated using density functional theory (DFT) in combination with CPCM solvation model. In the first hydrolysis step, faster aquation is observed in the case of DMSO hydrolysis from Os-NAMI-A in comparison to the chloro ligand having activation Gibbs free energy (Δ
G
aq
) value of 24.66 kcal mol
−1
, which is in good agreement with the experimental results. On the other hand, the second hydrolysis is mainly performed
via
the first chloro ligand hydrolysed Os-NAMI-A to form
cis
-[OsCl
2
(H
2
O)
2
(DMSO)(Im)]
+
(
P-2B
). However, the hydrolysis of
cis
-diaquated Os-NAMI-A [OsCl
3
(H
2
O)
2
(Im)] (
P-2A
) shows enhanced feasibility in the third hydrolysis step with the lowest activation Gibbs free energy (17.27 kcal mol
−1
) and the rate constant value is computed to be 1.34 s
−1
. Additionally, it is observed that hydrogen bonding plays an important role in stabilizing the intermediates and transition states. Furthermore, calculated net atomic charges based on natural population analysis show charge redistribution during hydrolysis reactions.
Detailed hydrolysis mechanism of osmium(
iii
) anticancer drug, (ImH)[
trans
-OsCl
4
(DMSO)(Im)] (Os-NAMI-A; Im = imidazole, DMSO = dimethyl sulfoxide) has been investigated using density functional theory (DFT) in combination with CPCM solvation model.</description><subject>Activation energy</subject><subject>Cancer</subject><subject>Cartesian coordinates</subject><subject>Density functional theory</subject><subject>Dimethyl sulfoxide</subject><subject>Gibbs free energy</subject><subject>Hydrogen bonding</subject><subject>Hydrolysis</subject><subject>Imidazole</subject><subject>Ligands</subject><subject>Osmium</subject><subject>Quantum chemistry</subject><subject>Solvation</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpFkU1Lw0AQhoMoWKsX78KCl0aM7kc-EQ-h9SPSNgf1JBI2m02zJZu0u4lQ_4f_160VhYEZhmfeYd6xrFMErxAk0XWBmiWEQUjonjVAxI-cCPto39TIdR3ouf6hdaS1YRAKfDSwvmJQ8I6Kmhdg3dOm6yVgFZeC0RqI5oPrTixoJ9oGmOgqDqpNodp6o4UGkrOKNkJL0Jag1VL0cmQDI2KmG8YVKFS_uASjRD7ab06qx_VoMntObdOw38Eo1c48niVOfAMSCW6BkKKgn23N7WProKS15ie_eWi93t-9jB-dafqQjOOpw3CIOsfj0OWc5hBhCkMW8jyPEPUI91mJvSLwvSCPMMMkgJAwNy891815EUTUZTAMERla5zvdlWrXvbk1W7a9aszKDHvQx6FP8Ja62FFMtVorXmYrJSRVmwzBbGt7NkHzpx_bYwOf7WCl2R_3_xbyDZRTfVs</recordid><startdate>20210329</startdate><enddate>20210329</enddate><creator>Pradhan, Amit Kumar</creator><creator>Shyam, Abhijit</creator><creator>Mondal, Paritosh</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0003-1089-1620</orcidid></search><sort><creationdate>20210329</creationdate><title>A detailed quantum chemical investigation on the hydrolysis mechanism of osmium() anticancer drug, (ImH)[-OsCl(DMSO)(Im)] (Os-NAMI-A; Im = imidazole)</title><author>Pradhan, Amit Kumar ; Shyam, Abhijit ; Mondal, Paritosh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-5e04eeab012a08c8ebb91a53e6cf25d7657b92c237003c4bf544bed79a4c08813</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Activation energy</topic><topic>Cancer</topic><topic>Cartesian coordinates</topic><topic>Density functional theory</topic><topic>Dimethyl sulfoxide</topic><topic>Gibbs free energy</topic><topic>Hydrogen bonding</topic><topic>Hydrolysis</topic><topic>Imidazole</topic><topic>Ligands</topic><topic>Osmium</topic><topic>Quantum chemistry</topic><topic>Solvation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pradhan, Amit Kumar</creatorcontrib><creatorcontrib>Shyam, Abhijit</creatorcontrib><creatorcontrib>Mondal, Paritosh</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pradhan, Amit Kumar</au><au>Shyam, Abhijit</au><au>Mondal, Paritosh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A detailed quantum chemical investigation on the hydrolysis mechanism of osmium() anticancer drug, (ImH)[-OsCl(DMSO)(Im)] (Os-NAMI-A; Im = imidazole)</atitle><jtitle>New journal of chemistry</jtitle><date>2021-03-29</date><risdate>2021</risdate><volume>45</volume><issue>12</issue><spage>5682</spage><epage>5694</epage><pages>5682-5694</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>Detailed hydrolysis mechanism of osmium(
iii
) anticancer drug, (ImH)[
trans
-OsCl
4
(DMSO)(Im)] (Os-NAMI-A; Im = imidazole, DMSO = dimethyl sulfoxide) has been investigated using density functional theory (DFT) in combination with CPCM solvation model. In the first hydrolysis step, faster aquation is observed in the case of DMSO hydrolysis from Os-NAMI-A in comparison to the chloro ligand having activation Gibbs free energy (Δ
G
aq
) value of 24.66 kcal mol
−1
, which is in good agreement with the experimental results. On the other hand, the second hydrolysis is mainly performed
via
the first chloro ligand hydrolysed Os-NAMI-A to form
cis
-[OsCl
2
(H
2
O)
2
(DMSO)(Im)]
+
(
P-2B
). However, the hydrolysis of
cis
-diaquated Os-NAMI-A [OsCl
3
(H
2
O)
2
(Im)] (
P-2A
) shows enhanced feasibility in the third hydrolysis step with the lowest activation Gibbs free energy (17.27 kcal mol
−1
) and the rate constant value is computed to be 1.34 s
−1
. Additionally, it is observed that hydrogen bonding plays an important role in stabilizing the intermediates and transition states. Furthermore, calculated net atomic charges based on natural population analysis show charge redistribution during hydrolysis reactions.
Detailed hydrolysis mechanism of osmium(
iii
) anticancer drug, (ImH)[
trans
-OsCl
4
(DMSO)(Im)] (Os-NAMI-A; Im = imidazole, DMSO = dimethyl sulfoxide) has been investigated using density functional theory (DFT) in combination with CPCM solvation model.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1nj00783a</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0003-1089-1620</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2021-03, Vol.45 (12), p.5682-5694 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Activation energy Cancer Cartesian coordinates Density functional theory Dimethyl sulfoxide Gibbs free energy Hydrogen bonding Hydrolysis Imidazole Ligands Osmium Quantum chemistry Solvation |
| title | A detailed quantum chemical investigation on the hydrolysis mechanism of osmium() anticancer drug, (ImH)[-OsCl(DMSO)(Im)] (Os-NAMI-A; Im = imidazole) |
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