Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates
Two new azobenzene heptamethine cyanine conjugates exist as dispersed monomeric molecules in methanol solution and exhibit near-infrared (NIR) cyanine absorption and fluorescence. Both conjugates form non-emissive cyanine H-aggregates in water, but the addition of cucurbit[7]uril (CB7) induces dye d...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/17/5440 |
| _version_ | 1797494185216966656 |
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| author | Sai Shradha Reddy Kommidi Bradley D. Smith |
| author_facet | Sai Shradha Reddy Kommidi Bradley D. Smith |
| author_sort | Sai Shradha Reddy Kommidi |
| collection | DOAJ |
| description | Two new azobenzene heptamethine cyanine conjugates exist as dispersed monomeric molecules in methanol solution and exhibit near-infrared (NIR) cyanine absorption and fluorescence. Both conjugates form non-emissive cyanine H-aggregates in water, but the addition of cucurbit[7]uril (CB7) induces dye deaggregation and a large increase in cyanine NIR fluorescence emission intensity. CB7 encapsulates the protonated azonium tautomer of the 4-(<i>N</i>,<i>N</i>-dimethylamino)azobenzene component of each azobenzene–cyanine conjugate and produces a distinctive new absorption band at 534 nm. The complex is quite hydrophilic, which suggests that CB7 can be used as a supramolecular additive to solubilize this new family of NIR azobenzene–cyanine conjugates for future biomedical applications. Since many azobenzene compounds are themselves potential drug candidates or theranostic agents, it should be possible to formulate many of them as CB7 inclusion complexes with improved solubility, stability, and pharmaceutical profile. |
| first_indexed | 2024-03-10T01:30:43Z |
| format | Article |
| id | doaj.art-8979daa2b33e4106b3ee43ba65d7bbc1 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T01:30:43Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-8979daa2b33e4106b3ee43ba65d7bbc12023-11-23T13:42:05ZengMDPI AGMolecules1420-30492022-08-012717544010.3390/molecules27175440Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine ConjugatesSai Shradha Reddy Kommidi0Bradley D. Smith1Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, IN 46556, USADepartment of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, IN 46556, USATwo new azobenzene heptamethine cyanine conjugates exist as dispersed monomeric molecules in methanol solution and exhibit near-infrared (NIR) cyanine absorption and fluorescence. Both conjugates form non-emissive cyanine H-aggregates in water, but the addition of cucurbit[7]uril (CB7) induces dye deaggregation and a large increase in cyanine NIR fluorescence emission intensity. CB7 encapsulates the protonated azonium tautomer of the 4-(<i>N</i>,<i>N</i>-dimethylamino)azobenzene component of each azobenzene–cyanine conjugate and produces a distinctive new absorption band at 534 nm. The complex is quite hydrophilic, which suggests that CB7 can be used as a supramolecular additive to solubilize this new family of NIR azobenzene–cyanine conjugates for future biomedical applications. Since many azobenzene compounds are themselves potential drug candidates or theranostic agents, it should be possible to formulate many of them as CB7 inclusion complexes with improved solubility, stability, and pharmaceutical profile.https://www.mdpi.com/1420-3049/27/17/5440near-infrared fluorescencecyanine dye aggregationsupramolecular chemistryazobenzenecucurbituril |
| spellingShingle | Sai Shradha Reddy Kommidi Bradley D. Smith Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates Molecules near-infrared fluorescence cyanine dye aggregation supramolecular chemistry azobenzene cucurbituril |
| title | Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates |
| title_full | Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates |
| title_fullStr | Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates |
| title_full_unstemmed | Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates |
| title_short | Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates |
| title_sort | cucurbit 7 uril complexation of near infrared fluorescent azobenzene cyanine conjugates |
| topic | near-infrared fluorescence cyanine dye aggregation supramolecular chemistry azobenzene cucurbituril |
| url | https://www.mdpi.com/1420-3049/27/17/5440 |
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