Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation
We designed and synthesized two analogous pentacationic [60]fullerenyl monoadducts, C[subscript 60](>ME[subscript 1]N[subscript 6]+C[subscript 3]) (1) and C[subscript 60](>ME[subscript 3]N[subscript 6]+C[subscript 3]) (2), with variation of the methoxyethyleneglycol length. Each of these deriv...
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| Format: | Article |
| Language: | en_US |
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MDPI AG
2014
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| Online Access: | http://hdl.handle.net/1721.1/88108 |
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| author | Thota, Sammaiah Wang, Min Jeon, Seaho Maragani, Satyanarayana Hamblin, Michael R. Chiang, Long Y. |
| author2 | Harvard University--MIT Division of Health Sciences and Technology |
| author_facet | Harvard University--MIT Division of Health Sciences and Technology Thota, Sammaiah Wang, Min Jeon, Seaho Maragani, Satyanarayana Hamblin, Michael R. Chiang, Long Y. |
| author_sort | Thota, Sammaiah |
| collection | MIT |
| description | We designed and synthesized two analogous pentacationic [60]fullerenyl monoadducts, C[subscript 60](>ME[subscript 1]N[subscript 6]+C[subscript 3]) (1) and C[subscript 60](>ME[subscript 3]N[subscript 6]+C[subscript 3]) (2), with variation of the methoxyethyleneglycol length. Each of these derivatives bears a well-defined number of cationic charges aimed to enhance and control their ability to target pathogenic Gram-positive and Gram-negative bacterial cells for allowing photodynamic inactivation. The synthesis was achieved by the use of a common synthon of pentacationic N,N′,N,N,N,N-hexapropyl-hexa(aminoethyl)amine arm (C[subscript 3]N[subscript 6]+) having six attached propyl groups, instead of methyl or ethyl groups, to provide a well-balanced hydrophobicity–hydrophilicity character to pentacationic precursor intermediates and better compatibility with the highly hydrophobic C[subscript 60] cage moiety. We demonstrated two plausible synthetic routes for the preparation of 1 and 2 with the product characterization via various spectroscopic methods. |
| first_indexed | 2024-09-23T15:09:39Z |
| format | Article |
| id | mit-1721.1/88108 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T15:09:39Z |
| publishDate | 2014 |
| publisher | MDPI AG |
| record_format | dspace |
| spelling | mit-1721.1/881082022-10-02T00:58:18Z Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation Thota, Sammaiah Wang, Min Jeon, Seaho Maragani, Satyanarayana Hamblin, Michael R. Chiang, Long Y. Harvard University--MIT Division of Health Sciences and Technology Hamblin, Michael R. We designed and synthesized two analogous pentacationic [60]fullerenyl monoadducts, C[subscript 60](>ME[subscript 1]N[subscript 6]+C[subscript 3]) (1) and C[subscript 60](>ME[subscript 3]N[subscript 6]+C[subscript 3]) (2), with variation of the methoxyethyleneglycol length. Each of these derivatives bears a well-defined number of cationic charges aimed to enhance and control their ability to target pathogenic Gram-positive and Gram-negative bacterial cells for allowing photodynamic inactivation. The synthesis was achieved by the use of a common synthon of pentacationic N,N′,N,N,N,N-hexapropyl-hexa(aminoethyl)amine arm (C[subscript 3]N[subscript 6]+) having six attached propyl groups, instead of methyl or ethyl groups, to provide a well-balanced hydrophobicity–hydrophilicity character to pentacationic precursor intermediates and better compatibility with the highly hydrophobic C[subscript 60] cage moiety. We demonstrated two plausible synthetic routes for the preparation of 1 and 2 with the product characterization via various spectroscopic methods. National Institutes of Health (U.S.) (Grant R01CA137108) 2014-06-30T11:55:15Z 2014-06-30T11:55:15Z 2012-05 2012-04 Article http://purl.org/eprint/type/JournalArticle 1420-3049 http://hdl.handle.net/1721.1/88108 Thota, Sammaiah, Min Wang, Seaho Jeon, Satyanarayana Maragani, Michael R. Hamblin, and Long Y. Chiang. “Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation.” Molecules 17, no. 12 (May 7, 2012): 5225–5243. en_US http://dx.doi.org/10.3390/molecules17055225 Molecules Creative Commons Attribution http://creativecommons.org/licenses/by/3.0/ application/pdf MDPI AG MDPI Publishing |
| spellingShingle | Thota, Sammaiah Wang, Min Jeon, Seaho Maragani, Satyanarayana Hamblin, Michael R. Chiang, Long Y. Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation |
| title | Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation |
| title_full | Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation |
| title_fullStr | Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation |
| title_full_unstemmed | Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation |
| title_short | Synthesis and Characterization of Positively Charged Pentacationic [60]Fullerene Monoadducts for Antimicrobial Photodynamic Inactivation |
| title_sort | synthesis and characterization of positively charged pentacationic 60 fullerene monoadducts for antimicrobial photodynamic inactivation |
| url | http://hdl.handle.net/1721.1/88108 |
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