Inspecting the structural characteristics of chiral drug penicillamine under different pH conditions using Raman optical activity spectroscopy and DFT calculations
The investigation of the structural characteristics of chiral drugs in physiological environments is a challenging research topic, which may lead to a better understanding of how the drugs work. Raman optical activity (ROA) spectroscopy in combination with density functional theory (DFT) calculation...
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Veröffentlicht in: | Physical chemistry chemical physics : PCCP 2021-10, Vol.23 (38), p.22119-22132 |
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description | The investigation of the structural characteristics of chiral drugs in physiological environments is a challenging research topic, which may lead to a better understanding of how the drugs work. Raman optical activity (ROA) spectroscopy in combination with density functional theory (DFT) calculations was exploited to inspect the structural changes in penicillamine under different acid-base states in aqueous solutions. The B3LYP/aug-cc-PVDZ method was employed and the implicit solvation model density (SMD) was considered for describing the solvation effect in H
2
O. The conformations of penicillamine varied with pH, but penicillamine was liable to stabilize in the form of the P
C
conformation (the sulfur atom is in a
trans
orientation with respect to carboxylate) in most cases for both
d
- and
l
-isomers. The relationship between the conformations of penicillamine and the ROA peaks, as well as peak assignments, were comprehensively studied and elucidated. In the fingerprint region, two ROA couplets and one ROA triplet with different patterns were recognized. The intensity, sign and frequency of the corresponding peaks also changed with varying pH. Deuteration was carried out to identify the vibrational modes, and the ROA peaks of the deuterated amino group in particular are sensitive to change in the ambient environment. The results are expected not only to serve as a reference for the interpretation of the ROA spectra of penicillamine and other chiral drugs with analogous structures but also to evaluate the structural changes of chiral molecules in physiological environments, which will form the basis of further exploration of the effects of structural characteristics on the pharmacological and toxicological properties of chiral drugs.
The structural characteristics of penicillamine and the influence of pH were characterized using Raman optical activity spectroscopy and density functional theory calculations. |
doi_str_mv | 10.1039/d1cp02219a |
format | Article |
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2
O. The conformations of penicillamine varied with pH, but penicillamine was liable to stabilize in the form of the P
C
conformation (the sulfur atom is in a
trans
orientation with respect to carboxylate) in most cases for both
d
- and
l
-isomers. The relationship between the conformations of penicillamine and the ROA peaks, as well as peak assignments, were comprehensively studied and elucidated. In the fingerprint region, two ROA couplets and one ROA triplet with different patterns were recognized. The intensity, sign and frequency of the corresponding peaks also changed with varying pH. Deuteration was carried out to identify the vibrational modes, and the ROA peaks of the deuterated amino group in particular are sensitive to change in the ambient environment. The results are expected not only to serve as a reference for the interpretation of the ROA spectra of penicillamine and other chiral drugs with analogous structures but also to evaluate the structural changes of chiral molecules in physiological environments, which will form the basis of further exploration of the effects of structural characteristics on the pharmacological and toxicological properties of chiral drugs.
The structural characteristics of penicillamine and the influence of pH were characterized using Raman optical activity spectroscopy and density functional theory calculations.</description><identifier>ISSN: 1463-9076</identifier><identifier>EISSN: 1463-9084</identifier><identifier>DOI: 10.1039/d1cp02219a</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aqueous solutions ; Density functional theory ; Deuteration ; Drugs ; Isomers ; Optical activity ; Pattern recognition ; Physiology ; Solvation ; Spectroscopy ; Spectrum analysis</subject><ispartof>Physical chemistry chemical physics : PCCP, 2021-10, Vol.23 (38), p.22119-22132</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c273t-b46dd47ed4b25b0edce1e87bb545741a49447817a5ae67d26a371f3f21120e913</cites><orcidid>0000-0001-6382-2333 ; 0000-0002-9775-8189 ; 0000-0001-5260-2861</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Guo, Yu-Ting</creatorcontrib><creatorcontrib>Xiao, Yuan-Hui</creatorcontrib><creatorcontrib>Zhang, Ji-Guang</creatorcontrib><creatorcontrib>Bian, Si-Da</creatorcontrib><creatorcontrib>Zhou, Jian-Zhang</creatorcontrib><creatorcontrib>Wu, De-Yin</creatorcontrib><creatorcontrib>Tian, Zhong-Qun</creatorcontrib><title>Inspecting the structural characteristics of chiral drug penicillamine under different pH conditions using Raman optical activity spectroscopy and DFT calculations</title><title>Physical chemistry chemical physics : PCCP</title><description>The investigation of the structural characteristics of chiral drugs in physiological environments is a challenging research topic, which may lead to a better understanding of how the drugs work. Raman optical activity (ROA) spectroscopy in combination with density functional theory (DFT) calculations was exploited to inspect the structural changes in penicillamine under different acid-base states in aqueous solutions. The B3LYP/aug-cc-PVDZ method was employed and the implicit solvation model density (SMD) was considered for describing the solvation effect in H
2
O. The conformations of penicillamine varied with pH, but penicillamine was liable to stabilize in the form of the P
C
conformation (the sulfur atom is in a
trans
orientation with respect to carboxylate) in most cases for both
d
- and
l
-isomers. The relationship between the conformations of penicillamine and the ROA peaks, as well as peak assignments, were comprehensively studied and elucidated. In the fingerprint region, two ROA couplets and one ROA triplet with different patterns were recognized. The intensity, sign and frequency of the corresponding peaks also changed with varying pH. Deuteration was carried out to identify the vibrational modes, and the ROA peaks of the deuterated amino group in particular are sensitive to change in the ambient environment. The results are expected not only to serve as a reference for the interpretation of the ROA spectra of penicillamine and other chiral drugs with analogous structures but also to evaluate the structural changes of chiral molecules in physiological environments, which will form the basis of further exploration of the effects of structural characteristics on the pharmacological and toxicological properties of chiral drugs.
The structural characteristics of penicillamine and the influence of pH were characterized using Raman optical activity spectroscopy and density functional theory calculations.</description><subject>Aqueous solutions</subject><subject>Density functional theory</subject><subject>Deuteration</subject><subject>Drugs</subject><subject>Isomers</subject><subject>Optical activity</subject><subject>Pattern recognition</subject><subject>Physiology</subject><subject>Solvation</subject><subject>Spectroscopy</subject><subject>Spectrum analysis</subject><issn>1463-9076</issn><issn>1463-9084</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdkctKAzEUhgdR8LpxLwTciFDNbSadZam3QkERXQ-Z5IymTJMxF6HP44uatqLgKiHny5ec8xfFKcFXBLP6WhM1YEpJLXeKA8IrNqrxmO_-7kW1XxyGsMAYk5Kwg-JrZsMAKhr7huI7oBB9UjF52SP1Lr1UEbwJ0aiAXJePzLqifXpDA1ijTN_LpbGAktXgkTZdBx5sRMMDUs5qE42zAaWw9j_LpbTIDdmWJVltPk1coc373gXlhhWSVqObuxeUCZV6ubl-XOx1sg9w8rMeFa93ty_Th9H88X42ncxHigoWRy2vtOYCNG9p2WLQCgiMRduWvBScSF5zLsZEyFJCJTStJBOkYx0lhGKoCTsqLrbewbuPBCE2SxMU5BYtuBQaWgrBS44xzej5P3Thkrf5d2uqZrXIo87U5ZZSub3goWsGb5bSrxqCm3VezQ2ZPm3ymmT4bAv7oH65vzzZN-nClaQ</recordid><startdate>20211006</startdate><enddate>20211006</enddate><creator>Guo, Yu-Ting</creator><creator>Xiao, Yuan-Hui</creator><creator>Zhang, Ji-Guang</creator><creator>Bian, Si-Da</creator><creator>Zhou, Jian-Zhang</creator><creator>Wu, De-Yin</creator><creator>Tian, Zhong-Qun</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6382-2333</orcidid><orcidid>https://orcid.org/0000-0002-9775-8189</orcidid><orcidid>https://orcid.org/0000-0001-5260-2861</orcidid></search><sort><creationdate>20211006</creationdate><title>Inspecting the structural characteristics of chiral drug penicillamine under different pH conditions using Raman optical activity spectroscopy and DFT calculations</title><author>Guo, Yu-Ting ; Xiao, Yuan-Hui ; Zhang, Ji-Guang ; Bian, Si-Da ; Zhou, Jian-Zhang ; Wu, De-Yin ; Tian, Zhong-Qun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c273t-b46dd47ed4b25b0edce1e87bb545741a49447817a5ae67d26a371f3f21120e913</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aqueous solutions</topic><topic>Density functional theory</topic><topic>Deuteration</topic><topic>Drugs</topic><topic>Isomers</topic><topic>Optical activity</topic><topic>Pattern recognition</topic><topic>Physiology</topic><topic>Solvation</topic><topic>Spectroscopy</topic><topic>Spectrum analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Guo, Yu-Ting</creatorcontrib><creatorcontrib>Xiao, Yuan-Hui</creatorcontrib><creatorcontrib>Zhang, Ji-Guang</creatorcontrib><creatorcontrib>Bian, Si-Da</creatorcontrib><creatorcontrib>Zhou, Jian-Zhang</creatorcontrib><creatorcontrib>Wu, De-Yin</creatorcontrib><creatorcontrib>Tian, Zhong-Qun</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Physical chemistry chemical physics : PCCP</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Guo, Yu-Ting</au><au>Xiao, Yuan-Hui</au><au>Zhang, Ji-Guang</au><au>Bian, Si-Da</au><au>Zhou, Jian-Zhang</au><au>Wu, De-Yin</au><au>Tian, Zhong-Qun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inspecting the structural characteristics of chiral drug penicillamine under different pH conditions using Raman optical activity spectroscopy and DFT calculations</atitle><jtitle>Physical chemistry chemical physics : PCCP</jtitle><date>2021-10-06</date><risdate>2021</risdate><volume>23</volume><issue>38</issue><spage>22119</spage><epage>22132</epage><pages>22119-22132</pages><issn>1463-9076</issn><eissn>1463-9084</eissn><abstract>The investigation of the structural characteristics of chiral drugs in physiological environments is a challenging research topic, which may lead to a better understanding of how the drugs work. Raman optical activity (ROA) spectroscopy in combination with density functional theory (DFT) calculations was exploited to inspect the structural changes in penicillamine under different acid-base states in aqueous solutions. The B3LYP/aug-cc-PVDZ method was employed and the implicit solvation model density (SMD) was considered for describing the solvation effect in H
2
O. The conformations of penicillamine varied with pH, but penicillamine was liable to stabilize in the form of the P
C
conformation (the sulfur atom is in a
trans
orientation with respect to carboxylate) in most cases for both
d
- and
l
-isomers. The relationship between the conformations of penicillamine and the ROA peaks, as well as peak assignments, were comprehensively studied and elucidated. In the fingerprint region, two ROA couplets and one ROA triplet with different patterns were recognized. The intensity, sign and frequency of the corresponding peaks also changed with varying pH. Deuteration was carried out to identify the vibrational modes, and the ROA peaks of the deuterated amino group in particular are sensitive to change in the ambient environment. The results are expected not only to serve as a reference for the interpretation of the ROA spectra of penicillamine and other chiral drugs with analogous structures but also to evaluate the structural changes of chiral molecules in physiological environments, which will form the basis of further exploration of the effects of structural characteristics on the pharmacological and toxicological properties of chiral drugs.
The structural characteristics of penicillamine and the influence of pH were characterized using Raman optical activity spectroscopy and density functional theory calculations.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1cp02219a</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0001-6382-2333</orcidid><orcidid>https://orcid.org/0000-0002-9775-8189</orcidid><orcidid>https://orcid.org/0000-0001-5260-2861</orcidid></addata></record> |
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subjects | Aqueous solutions Density functional theory Deuteration Drugs Isomers Optical activity Pattern recognition Physiology Solvation Spectroscopy Spectrum analysis |
title | Inspecting the structural characteristics of chiral drug penicillamine under different pH conditions using Raman optical activity spectroscopy and DFT calculations |
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