Synthesis of water-soluble porphyrin with tyrosine fragments and study of its interaction with S-protein of SARS-CoV-2
The multistage purposeful synthesis of 5,15-bis(4′- l - N -tyrosinylamidophenyl)-10,20-bis( N -methylpyridin-3′-yl)porphine diiodide was carried out, and the optimum synthesis conditions were determined. 5,15-Bis(4′-nitrophenyl)-10,20-bis(pyridin-3′-yl)porphine served as the starting porphyrin. The...
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| Veröffentlicht in: | Russian chemical bulletin 2022, Vol.71 (11), p.2495-2504 |
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| creator | Syrbu, S. A. Semeikin, A. S. Lebedeva, N. Sh Gubarev, Yu. A. Yurina, E. S. Guseinov, S. S. Koifman, O. I. |
| description | The multistage purposeful synthesis of 5,15-bis(4′-
l
-
N
-tyrosinylamidophenyl)-10,20-bis(
N
-methylpyridin-3′-yl)porphine diiodide was carried out, and the optimum synthesis conditions were determined. 5,15-Bis(4′-nitrophenyl)-10,20-bis(pyridin-3′-yl)porphine served as the starting porphyrin. The structure, individual character, and purity of the target compound were proved by electron spectroscopy,
1
H NMR spectroscopy, mass spectrometry (MALDI TOF), and TLC. Specific features of the interaction of the synthesized porphyrin with S-protein of SARS-CoV-2 were studied using spectral and thermochemical methods, including conditions of photoirradiation. The photoirradiation of the synthesized porphyrin in a complex with the SARS-CoV-2 S-protein can result in the partial oxidation of amino acid residues of the protein and distort its primary and secondary structures. The photoirradiation of the S-protein complex with the porphyrin decreases its thermal resistance to melting by 15 °C compared to the free S-protein and causes porphyrin release. |
| doi_str_mv | 10.1007/s11172-022-3679-8 |
| format | Article |
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l
-
N
-tyrosinylamidophenyl)-10,20-bis(
N
-methylpyridin-3′-yl)porphine diiodide was carried out, and the optimum synthesis conditions were determined. 5,15-Bis(4′-nitrophenyl)-10,20-bis(pyridin-3′-yl)porphine served as the starting porphyrin. The structure, individual character, and purity of the target compound were proved by electron spectroscopy,
1
H NMR spectroscopy, mass spectrometry (MALDI TOF), and TLC. Specific features of the interaction of the synthesized porphyrin with S-protein of SARS-CoV-2 were studied using spectral and thermochemical methods, including conditions of photoirradiation. The photoirradiation of the synthesized porphyrin in a complex with the SARS-CoV-2 S-protein can result in the partial oxidation of amino acid residues of the protein and distort its primary and secondary structures. The photoirradiation of the S-protein complex with the porphyrin decreases its thermal resistance to melting by 15 °C compared to the free S-protein and causes porphyrin release.</description><identifier>ISSN: 1066-5285</identifier><identifier>EISSN: 1573-9171</identifier><identifier>DOI: 10.1007/s11172-022-3679-8</identifier><identifier>PMID: 36569660</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Amino acids ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Full ; Full Articles ; Inorganic Chemistry ; Mass spectrometry ; NMR spectroscopy ; Organic Chemistry ; Oxidation ; Porphyrins ; Proteins ; Severe acute respiratory syndrome coronavirus 2 ; Synthesis ; Thermal resistance ; Tyrosine</subject><ispartof>Russian chemical bulletin, 2022, Vol.71 (11), p.2495-2504</ispartof><rights>Springer Science+Business Media LLC 2022</rights><rights>Springer Science+Business Media LLC 2022.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c470t-8c8dad9c9219cb187d6a22c816767dd6da6885480ec025da6990d7c5e656fc6b3</citedby><cites>FETCH-LOGICAL-c470t-8c8dad9c9219cb187d6a22c816767dd6da6885480ec025da6990d7c5e656fc6b3</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/s11172-022-3679-8$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11172-022-3679-8$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>230,314,780,784,885,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36569660$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Syrbu, S. A.</creatorcontrib><creatorcontrib>Semeikin, A. S.</creatorcontrib><creatorcontrib>Lebedeva, N. Sh</creatorcontrib><creatorcontrib>Gubarev, Yu. A.</creatorcontrib><creatorcontrib>Yurina, E. S.</creatorcontrib><creatorcontrib>Guseinov, S. S.</creatorcontrib><creatorcontrib>Koifman, O. I.</creatorcontrib><title>Synthesis of water-soluble porphyrin with tyrosine fragments and study of its interaction with S-protein of SARS-CoV-2</title><title>Russian chemical bulletin</title><addtitle>Russ Chem Bull</addtitle><addtitle>Russ Chem Bull</addtitle><description>The multistage purposeful synthesis of 5,15-bis(4′-
l
-
N
-tyrosinylamidophenyl)-10,20-bis(
N
-methylpyridin-3′-yl)porphine diiodide was carried out, and the optimum synthesis conditions were determined. 5,15-Bis(4′-nitrophenyl)-10,20-bis(pyridin-3′-yl)porphine served as the starting porphyrin. The structure, individual character, and purity of the target compound were proved by electron spectroscopy,
1
H NMR spectroscopy, mass spectrometry (MALDI TOF), and TLC. Specific features of the interaction of the synthesized porphyrin with S-protein of SARS-CoV-2 were studied using spectral and thermochemical methods, including conditions of photoirradiation. The photoirradiation of the synthesized porphyrin in a complex with the SARS-CoV-2 S-protein can result in the partial oxidation of amino acid residues of the protein and distort its primary and secondary structures. The photoirradiation of the S-protein complex with the porphyrin decreases its thermal resistance to melting by 15 °C compared to the free S-protein and causes porphyrin release.</description><subject>Amino acids</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Full</subject><subject>Full Articles</subject><subject>Inorganic Chemistry</subject><subject>Mass spectrometry</subject><subject>NMR spectroscopy</subject><subject>Organic Chemistry</subject><subject>Oxidation</subject><subject>Porphyrins</subject><subject>Proteins</subject><subject>Severe acute respiratory syndrome coronavirus 2</subject><subject>Synthesis</subject><subject>Thermal resistance</subject><subject>Tyrosine</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp1kUuLFDEUhQtRnIf-ADdS4MZNNElVXhthaNQRBgRb3YZ0kurOUJ2USWqG-vfeptvxAa7yuN85uTenaV4Q_IZgLN4WQoigCFOKOi4Uko-ac8JEhxQR5DHsMeeIUcnOmotSbjHGVEr5tDnrOOOKc3ze3K2XWHe-hNKmob031WdU0jhvRt9OKU-7JYfY3oe6a-uSUwnRt0M2272PtbQmurbU2S0HcYCLEMHA2BrSSbRGU07VgwcQ66sva7RK3xF91jwZzFj889N62Xz78P7r6hrdfP74aXV1g2wvcEXSSmecsooSZTdECscNpVYSLrhwjjvDpWS9xN5iyuCkFHbCMg_zDZZvusvm3dF3mjd77yx0nc2opxz2Ji86maD_rsSw09t0p5XglHcMDF6fDHL6MftS9T4U68fRRJ_moqlgsmOi73tAX_2D3qY5RxjvQDGpCHw6UORIWfjNkv3w0AzB-pCqPqaqIVV9SFVL0Lz8c4oHxa8YAaBHoEApbn3-_fT_XX8CGKGvNQ</recordid><startdate>2022</startdate><enddate>2022</enddate><creator>Syrbu, S. A.</creator><creator>Semeikin, A. S.</creator><creator>Lebedeva, N. Sh</creator><creator>Gubarev, Yu. A.</creator><creator>Yurina, E. S.</creator><creator>Guseinov, S. S.</creator><creator>Koifman, O. I.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>2022</creationdate><title>Synthesis of water-soluble porphyrin with tyrosine fragments and study of its interaction with S-protein of SARS-CoV-2</title><author>Syrbu, S. A. ; Semeikin, A. S. ; Lebedeva, N. Sh ; Gubarev, Yu. A. ; Yurina, E. S. ; Guseinov, S. S. ; Koifman, O. I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c470t-8c8dad9c9219cb187d6a22c816767dd6da6885480ec025da6990d7c5e656fc6b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Amino acids</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Full</topic><topic>Full Articles</topic><topic>Inorganic Chemistry</topic><topic>Mass spectrometry</topic><topic>NMR spectroscopy</topic><topic>Organic Chemistry</topic><topic>Oxidation</topic><topic>Porphyrins</topic><topic>Proteins</topic><topic>Severe acute respiratory syndrome coronavirus 2</topic><topic>Synthesis</topic><topic>Thermal resistance</topic><topic>Tyrosine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Syrbu, S. A.</creatorcontrib><creatorcontrib>Semeikin, A. S.</creatorcontrib><creatorcontrib>Lebedeva, N. Sh</creatorcontrib><creatorcontrib>Gubarev, Yu. A.</creatorcontrib><creatorcontrib>Yurina, E. S.</creatorcontrib><creatorcontrib>Guseinov, S. S.</creatorcontrib><creatorcontrib>Koifman, O. I.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Russian chemical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Syrbu, S. A.</au><au>Semeikin, A. S.</au><au>Lebedeva, N. Sh</au><au>Gubarev, Yu. A.</au><au>Yurina, E. S.</au><au>Guseinov, S. S.</au><au>Koifman, O. I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of water-soluble porphyrin with tyrosine fragments and study of its interaction with S-protein of SARS-CoV-2</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><addtitle>Russ Chem Bull</addtitle><date>2022</date><risdate>2022</risdate><volume>71</volume><issue>11</issue><spage>2495</spage><epage>2504</epage><pages>2495-2504</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>The multistage purposeful synthesis of 5,15-bis(4′-
l
-
N
-tyrosinylamidophenyl)-10,20-bis(
N
-methylpyridin-3′-yl)porphine diiodide was carried out, and the optimum synthesis conditions were determined. 5,15-Bis(4′-nitrophenyl)-10,20-bis(pyridin-3′-yl)porphine served as the starting porphyrin. The structure, individual character, and purity of the target compound were proved by electron spectroscopy,
1
H NMR spectroscopy, mass spectrometry (MALDI TOF), and TLC. Specific features of the interaction of the synthesized porphyrin with S-protein of SARS-CoV-2 were studied using spectral and thermochemical methods, including conditions of photoirradiation. The photoirradiation of the synthesized porphyrin in a complex with the SARS-CoV-2 S-protein can result in the partial oxidation of amino acid residues of the protein and distort its primary and secondary structures. The photoirradiation of the S-protein complex with the porphyrin decreases its thermal resistance to melting by 15 °C compared to the free S-protein and causes porphyrin release.</abstract><cop>New York</cop><pub>Springer US</pub><pmid>36569660</pmid><doi>10.1007/s11172-022-3679-8</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Russian chemical bulletin, 2022, Vol.71 (11), p.2495-2504 |
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| subjects | Amino acids Chemistry Chemistry and Materials Science Chemistry/Food Science Full Full Articles Inorganic Chemistry Mass spectrometry NMR spectroscopy Organic Chemistry Oxidation Porphyrins Proteins Severe acute respiratory syndrome coronavirus 2 Synthesis Thermal resistance Tyrosine |
| title | Synthesis of water-soluble porphyrin with tyrosine fragments and study of its interaction with S-protein of SARS-CoV-2 |
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