Physico-chemical evaluation of rationally designed melanins as novel nature-inspired radioprotectors
Melanin, a high-molecular weight pigment that is ubiquitous in nature, protects melanized microorganisms against high doses of ionizing radiation. However, the physics of melanin interaction with ionizing radiation is unknown. We rationally designed melanins from either 5-S-cysteinyl-DOPA, L-cystein...
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| description | Melanin, a high-molecular weight pigment that is ubiquitous in nature, protects melanized microorganisms against high doses of ionizing radiation. However, the physics of melanin interaction with ionizing radiation is unknown.
We rationally designed melanins from either 5-S-cysteinyl-DOPA, L-cysteine/L-DOPA, or L-DOPA with diverse structures as shown by elemental analysis and HPLC. Sulfur-containing melanins had higher predicted attenuation coefficients than non-sulfur-containing melanins. All synthetic melanins displayed strong electron paramagnetic resonance (2.14.10(18), 7.09.10(18), and 9.05.10(17) spins/g, respectively), with sulfur-containing melanins demonstrating more complex spectra and higher numbers of stable free radicals. There was no change in the quality or quantity of the stable free radicals after high-dose (30,000 cGy), high-energy ((137)Cs, 661.6 keV) irradiation, indicating a high degree of radical stability as well as a robust resistance to the ionizing effects of gamma irradiation. The rationally designed melanins protected mammalian cells against ionizing radiation of different energies.
We propose that due to melanin's numerous aromatic oligomers containing multiple pi-electron system, a generated Compton recoil electron gradually loses energy while passing through the pigment, until its energy is sufficiently low that it can be trapped by stable free radicals present in the pigment. Controlled dissipation of high-energy recoil electrons by melanin prevents secondary ionizations and the generation of damaging free radical species. |
| doi_str_mv | 10.1371/journal.pone.0007229 |
| format | Article |
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We rationally designed melanins from either 5-S-cysteinyl-DOPA, L-cysteine/L-DOPA, or L-DOPA with diverse structures as shown by elemental analysis and HPLC. Sulfur-containing melanins had higher predicted attenuation coefficients than non-sulfur-containing melanins. All synthetic melanins displayed strong electron paramagnetic resonance (2.14.10(18), 7.09.10(18), and 9.05.10(17) spins/g, respectively), with sulfur-containing melanins demonstrating more complex spectra and higher numbers of stable free radicals. There was no change in the quality or quantity of the stable free radicals after high-dose (30,000 cGy), high-energy ((137)Cs, 661.6 keV) irradiation, indicating a high degree of radical stability as well as a robust resistance to the ionizing effects of gamma irradiation. The rationally designed melanins protected mammalian cells against ionizing radiation of different energies.
We propose that due to melanin's numerous aromatic oligomers containing multiple pi-electron system, a generated Compton recoil electron gradually loses energy while passing through the pigment, until its energy is sufficiently low that it can be trapped by stable free radicals present in the pigment. Controlled dissipation of high-energy recoil electrons by melanin prevents secondary ionizations and the generation of damaging free radical species.</description><identifier>ISSN: 1932-6203</identifier><identifier>EISSN: 1932-6203</identifier><identifier>DOI: 10.1371/journal.pone.0007229</identifier><identifier>PMID: 19789711</identifier><language>eng</language><publisher>United States: Public Library of Science</publisher><subject>Animals ; Attenuation coefficients ; Biophysics/Experimental Biophysical Methods ; Cesium radioisotopes ; Chemistry/Biochemistry ; CHO Cells ; Cricetinae ; Cricetulus ; Cryptococcus neoformans - metabolism ; Cysteine - chemistry ; Cysteinyldopa - chemistry ; Damage prevention ; Dihydroxyphenylalanine ; Dopa ; Dopamine ; Dosimetry ; Drug dosages ; Electron paramagnetic resonance ; Electrons ; Energy ; Free Radicals ; Gamma irradiation ; Gamma Rays ; High performance liquid chromatography ; Immunology ; Ionization ; Ionizing radiation ; Irradiation ; Levodopa ; Levodopa - chemistry ; Liquid chromatography ; Mammalian cells ; Manganese Compounds - pharmacology ; Melanin ; Melanins - metabolism ; Melanins - physiology ; Microorganisms ; Migraine ; Molecular Weight ; Monte Carlo simulation ; Nuclear medicine ; Oligomers ; Oxides - pharmacology ; Oxygen - chemistry ; Physics ; Physics/Interdisciplinary Physics ; Radiation ; Radiation therapy ; Radiation Tolerance ; Radiation, Ionizing ; Recoil ; Spectrum analysis ; Sulfur ; Sulfur compounds ; X rays</subject><ispartof>PloS one, 2009-09, Vol.4 (9), p.e7229</ispartof><rights>COPYRIGHT 2009 Public Library of Science</rights><rights>2009 Schweitzer et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License (the “License”), which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>Schweitzer et al. 2009</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c663t-cea842a45d904af5cf6e134b1383af11c32d90fe540e8748fe177923ed493c543</citedby><cites>FETCH-LOGICAL-c663t-cea842a45d904af5cf6e134b1383af11c32d90fe540e8748fe177923ed493c543</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2749938/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2749938/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,2100,2926,23864,27922,27923,53789,53791,79370,79371</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19789711$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><contributor>Rubinsky, Boris</contributor><creatorcontrib>Schweitzer, Andrew D</creatorcontrib><creatorcontrib>Howell, Robertha C</creatorcontrib><creatorcontrib>Jiang, Zewei</creatorcontrib><creatorcontrib>Bryan, Ruth A</creatorcontrib><creatorcontrib>Gerfen, Gary</creatorcontrib><creatorcontrib>Chen, Chin-Cheng</creatorcontrib><creatorcontrib>Mah, Dennis</creatorcontrib><creatorcontrib>Cahill, Sean</creatorcontrib><creatorcontrib>Casadevall, Arturo</creatorcontrib><creatorcontrib>Dadachova, Ekaterina</creatorcontrib><title>Physico-chemical evaluation of rationally designed melanins as novel nature-inspired radioprotectors</title><title>PloS one</title><addtitle>PLoS One</addtitle><description>Melanin, a high-molecular weight pigment that is ubiquitous in nature, protects melanized microorganisms against high doses of ionizing radiation. However, the physics of melanin interaction with ionizing radiation is unknown.
We rationally designed melanins from either 5-S-cysteinyl-DOPA, L-cysteine/L-DOPA, or L-DOPA with diverse structures as shown by elemental analysis and HPLC. Sulfur-containing melanins had higher predicted attenuation coefficients than non-sulfur-containing melanins. All synthetic melanins displayed strong electron paramagnetic resonance (2.14.10(18), 7.09.10(18), and 9.05.10(17) spins/g, respectively), with sulfur-containing melanins demonstrating more complex spectra and higher numbers of stable free radicals. There was no change in the quality or quantity of the stable free radicals after high-dose (30,000 cGy), high-energy ((137)Cs, 661.6 keV) irradiation, indicating a high degree of radical stability as well as a robust resistance to the ionizing effects of gamma irradiation. The rationally designed melanins protected mammalian cells against ionizing radiation of different energies.
We propose that due to melanin's numerous aromatic oligomers containing multiple pi-electron system, a generated Compton recoil electron gradually loses energy while passing through the pigment, until its energy is sufficiently low that it can be trapped by stable free radicals present in the pigment. Controlled dissipation of high-energy recoil electrons by melanin prevents secondary ionizations and the generation of damaging free radical species.</description><subject>Animals</subject><subject>Attenuation coefficients</subject><subject>Biophysics/Experimental Biophysical Methods</subject><subject>Cesium radioisotopes</subject><subject>Chemistry/Biochemistry</subject><subject>CHO Cells</subject><subject>Cricetinae</subject><subject>Cricetulus</subject><subject>Cryptococcus neoformans - metabolism</subject><subject>Cysteine - chemistry</subject><subject>Cysteinyldopa - chemistry</subject><subject>Damage prevention</subject><subject>Dihydroxyphenylalanine</subject><subject>Dopa</subject><subject>Dopamine</subject><subject>Dosimetry</subject><subject>Drug dosages</subject><subject>Electron paramagnetic resonance</subject><subject>Electrons</subject><subject>Energy</subject><subject>Free Radicals</subject><subject>Gamma irradiation</subject><subject>Gamma Rays</subject><subject>High performance liquid chromatography</subject><subject>Immunology</subject><subject>Ionization</subject><subject>Ionizing radiation</subject><subject>Irradiation</subject><subject>Levodopa</subject><subject>Levodopa - chemistry</subject><subject>Liquid chromatography</subject><subject>Mammalian cells</subject><subject>Manganese Compounds - pharmacology</subject><subject>Melanin</subject><subject>Melanins - metabolism</subject><subject>Melanins - physiology</subject><subject>Microorganisms</subject><subject>Migraine</subject><subject>Molecular Weight</subject><subject>Monte Carlo simulation</subject><subject>Nuclear medicine</subject><subject>Oligomers</subject><subject>Oxides - pharmacology</subject><subject>Oxygen - chemistry</subject><subject>Physics</subject><subject>Physics/Interdisciplinary Physics</subject><subject>Radiation</subject><subject>Radiation therapy</subject><subject>Radiation Tolerance</subject><subject>Radiation, Ionizing</subject><subject>Recoil</subject><subject>Spectrum analysis</subject><subject>Sulfur</subject><subject>Sulfur compounds</subject><subject>X rays</subject><issn>1932-6203</issn><issn>1932-6203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>DOA</sourceid><recordid>eNqNkl2LEzEUhgdR3LX6D0QHBMGLqfmaZOZGWBY_Cgsrft2Gs5mTNks66SYzxf570-2o7YUguUg4ec6bc07eonhOyZxyRd_ehjH24Oeb0OOcEKIYax8U57TlrJKM8IdH57PiSUq3hNS8kfJxcUZb1bSK0vOi-7zaJWdCZVa4dgZ8iVvwIwwu9GWwZbw_gfe7ssPklj125Ro99K5PJaSyD1v0ZQ_DGLHKsY2LmYjQubCJYUAzhJieFo8s-ITPpn1WfP_w_tvlp-rq-uPi8uKqMlLyoTIIjWAg6q4lAmxtrETKxQ3lDQdLqeEs31isBcFGicYiVaplHDvRclMLPiteHnQ3PiQ9DShpylrGOGlYnYnFgegC3OpNdGuIOx3A6ftAiEsNcXDGowZjCbMoqVRMNF3XSKyZsFLV1uSieNZ6N7023qyxM9gPEfyJ6OlN71Z6GbaaKdG2uadZ8WoSiOFuxDT8o-T5gVpCrsr1NmQxk1e3_7D8-dbl-IVQrKmV4DInvDlJyMyAP4cljCnpxdcv_89e_zhlXx-xKwQ_rFLw494g6RQUB9DEkFJE-2cmlOi9d3_3qffe1ZN3c9qL43n-TZrMyn8Bot_smg</recordid><startdate>20090930</startdate><enddate>20090930</enddate><creator>Schweitzer, Andrew D</creator><creator>Howell, Robertha C</creator><creator>Jiang, Zewei</creator><creator>Bryan, Ruth A</creator><creator>Gerfen, Gary</creator><creator>Chen, Chin-Cheng</creator><creator>Mah, Dennis</creator><creator>Cahill, Sean</creator><creator>Casadevall, Arturo</creator><creator>Dadachova, Ekaterina</creator><general>Public Library of Science</general><general>Public Library of Science (PLoS)</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>IOV</scope><scope>ISR</scope><scope>3V.</scope><scope>7QG</scope><scope>7QL</scope><scope>7QO</scope><scope>7RV</scope><scope>7SN</scope><scope>7SS</scope><scope>7T5</scope><scope>7TG</scope><scope>7TM</scope><scope>7U9</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>KB0</scope><scope>KL.</scope><scope>L6V</scope><scope>LK8</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M7N</scope><scope>M7P</scope><scope>M7S</scope><scope>NAPCQ</scope><scope>P5Z</scope><scope>P62</scope><scope>P64</scope><scope>PATMY</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope><scope>PYCSY</scope><scope>RC3</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20090930</creationdate><title>Physico-chemical evaluation of rationally designed melanins as novel nature-inspired radioprotectors</title><author>Schweitzer, Andrew D ; Howell, Robertha C ; Jiang, Zewei ; Bryan, Ruth A ; Gerfen, Gary ; Chen, Chin-Cheng ; Mah, Dennis ; Cahill, Sean ; Casadevall, Arturo ; Dadachova, Ekaterina</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c663t-cea842a45d904af5cf6e134b1383af11c32d90fe540e8748fe177923ed493c543</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Animals</topic><topic>Attenuation coefficients</topic><topic>Biophysics/Experimental Biophysical Methods</topic><topic>Cesium radioisotopes</topic><topic>Chemistry/Biochemistry</topic><topic>CHO Cells</topic><topic>Cricetinae</topic><topic>Cricetulus</topic><topic>Cryptococcus neoformans - metabolism</topic><topic>Cysteine - chemistry</topic><topic>Cysteinyldopa - chemistry</topic><topic>Damage prevention</topic><topic>Dihydroxyphenylalanine</topic><topic>Dopa</topic><topic>Dopamine</topic><topic>Dosimetry</topic><topic>Drug dosages</topic><topic>Electron paramagnetic resonance</topic><topic>Electrons</topic><topic>Energy</topic><topic>Free Radicals</topic><topic>Gamma irradiation</topic><topic>Gamma Rays</topic><topic>High performance liquid chromatography</topic><topic>Immunology</topic><topic>Ionization</topic><topic>Ionizing radiation</topic><topic>Irradiation</topic><topic>Levodopa</topic><topic>Levodopa - chemistry</topic><topic>Liquid chromatography</topic><topic>Mammalian cells</topic><topic>Manganese Compounds - pharmacology</topic><topic>Melanin</topic><topic>Melanins - metabolism</topic><topic>Melanins - physiology</topic><topic>Microorganisms</topic><topic>Migraine</topic><topic>Molecular Weight</topic><topic>Monte Carlo simulation</topic><topic>Nuclear medicine</topic><topic>Oligomers</topic><topic>Oxides - 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However, the physics of melanin interaction with ionizing radiation is unknown.
We rationally designed melanins from either 5-S-cysteinyl-DOPA, L-cysteine/L-DOPA, or L-DOPA with diverse structures as shown by elemental analysis and HPLC. Sulfur-containing melanins had higher predicted attenuation coefficients than non-sulfur-containing melanins. All synthetic melanins displayed strong electron paramagnetic resonance (2.14.10(18), 7.09.10(18), and 9.05.10(17) spins/g, respectively), with sulfur-containing melanins demonstrating more complex spectra and higher numbers of stable free radicals. There was no change in the quality or quantity of the stable free radicals after high-dose (30,000 cGy), high-energy ((137)Cs, 661.6 keV) irradiation, indicating a high degree of radical stability as well as a robust resistance to the ionizing effects of gamma irradiation. The rationally designed melanins protected mammalian cells against ionizing radiation of different energies.
We propose that due to melanin's numerous aromatic oligomers containing multiple pi-electron system, a generated Compton recoil electron gradually loses energy while passing through the pigment, until its energy is sufficiently low that it can be trapped by stable free radicals present in the pigment. Controlled dissipation of high-energy recoil electrons by melanin prevents secondary ionizations and the generation of damaging free radical species.</abstract><cop>United States</cop><pub>Public Library of Science</pub><pmid>19789711</pmid><doi>10.1371/journal.pone.0007229</doi><tpages>e7229</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 1932-6203 |
| ispartof | PloS one, 2009-09, Vol.4 (9), p.e7229 |
| issn | 1932-6203 1932-6203 |
| language | eng |
| recordid | cdi_plos_journals_1292230825 |
| source | MEDLINE; DOAJ Directory of Open Access Journals; Public Library of Science (PLoS); EZB-FREE-00999 freely available EZB journals; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | Animals Attenuation coefficients Biophysics/Experimental Biophysical Methods Cesium radioisotopes Chemistry/Biochemistry CHO Cells Cricetinae Cricetulus Cryptococcus neoformans - metabolism Cysteine - chemistry Cysteinyldopa - chemistry Damage prevention Dihydroxyphenylalanine Dopa Dopamine Dosimetry Drug dosages Electron paramagnetic resonance Electrons Energy Free Radicals Gamma irradiation Gamma Rays High performance liquid chromatography Immunology Ionization Ionizing radiation Irradiation Levodopa Levodopa - chemistry Liquid chromatography Mammalian cells Manganese Compounds - pharmacology Melanin Melanins - metabolism Melanins - physiology Microorganisms Migraine Molecular Weight Monte Carlo simulation Nuclear medicine Oligomers Oxides - pharmacology Oxygen - chemistry Physics Physics/Interdisciplinary Physics Radiation Radiation therapy Radiation Tolerance Radiation, Ionizing Recoil Spectrum analysis Sulfur Sulfur compounds X rays |
| title | Physico-chemical evaluation of rationally designed melanins as novel nature-inspired radioprotectors |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T15%3A42%3A41IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-gale_plos_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Physico-chemical%20evaluation%20of%20rationally%20designed%20melanins%20as%20novel%20nature-inspired%20radioprotectors&rft.jtitle=PloS%20one&rft.au=Schweitzer,%20Andrew%20D&rft.date=2009-09-30&rft.volume=4&rft.issue=9&rft.spage=e7229&rft.pages=e7229-&rft.issn=1932-6203&rft.eissn=1932-6203&rft_id=info:doi/10.1371/journal.pone.0007229&rft_dat=%3Cgale_plos_%3EA472857436%3C/gale_plos_%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1292230825&rft_id=info:pmid/19789711&rft_galeid=A472857436&rft_doaj_id=oai_doaj_org_article_acf02fe6167248dd86e524f675fc34b3&rfr_iscdi=true |