Divergent Syntheses of Near-Infrared Light-Activated Molecular Jackhammers for Cancer Cell Eradication

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dc.citation.articleNumber2405965en_US
dc.citation.issueNumber45en_US
dc.citation.journalTitleAdvanced Scienceen_US
dc.citation.volumeNumber11en_US
dc.contributor.authorLi, Bowenen_US
dc.contributor.authorAyala-Orozco, Ciceronen_US
dc.contributor.authorSi, Tengdaen_US
dc.contributor.authorZhou, Lixinen_US
dc.contributor.authorWang, Zichengen_US
dc.contributor.authorMartí, Angel A.en_US
dc.contributor.authorTour, James M.en_US
dc.contributor.orgSmalley-Curl Institute;NanoCarbon Center;Rice Advanced Materials Instituteen_US
dc.date.accessioned2025-01-09T20:16:57Zen_US
dc.date.available2025-01-09T20:16:57Zen_US
dc.date.issued2024en_US
dc.description.abstractAminocyanines incorporating Cy7 and Cy7.5 moieties function as molecular jackhammers (MJH) through vibronic-driven action (VDA). This mechanism, which couples molecular vibrational and electronic modes, results in picosecond-scale concerted stretching of the entire molecule. When cell-associated and activated by near-infrared light, MJH mechanically disrupts cell membranes, causing rapid necrotic cell death. Unlike photodynamic and photothermal therapies, the ultrafast vibrational action of MJH is unhindered by high concentrations of reactive oxygen species scavengers and induces only a minimal temperature increase. Here, the efficient synthesis of a library of MJH is described using a practical approach to access a key intermediate and facilitating the preparation of various Cy7 and Cy7.5 MJH with diverse side chains in moderate to high yields. Photophysical characterization reveals that structural modifications significantly affect molar extinction coefficients and quantum yields while maintaining desirable absorption and emission wavelengths. The most promising compounds, featuring dimethylaminoethyl and dimethylcarbamoyl substitutions, demonstrate up to sevenfold improvement in phototherapeutic index compared to Cy7.5 amine across multiple cancer cell lines. This synthetic strategy provides a valuable platform for developing potent, light-activated therapeutic agents for cancer treatment, with potentially broad applicability across various cancer types.en_US
dc.identifier.citationLi, B., Ayala-Orozco, C., Si, T., Zhou, L., Wang, Z., Martí, A. A., & Tour, J. M. (2024). Divergent Syntheses of Near-Infrared Light-Activated Molecular Jackhammers for Cancer Cell Eradication. Advanced Science, 11(45), 2405965. https://doi.org/10.1002/advs.202405965en_US
dc.identifier.digitalDivergentSynthesesen_US
dc.identifier.doihttps://doi.org/10.1002/advs.202405965en_US
dc.identifier.urihttps://hdl.handle.net/1911/118102en_US
dc.language.isoengen_US
dc.publisherWileyen_US
dc.rightsExcept where otherwise noted, this work is licensed under a Creative Commons Attribution (CC BY) license. Permission to reuse, publish, or reproduce the work beyond the terms of the license or beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.en_US
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/en_US
dc.subject.keywordaminocyaninesen_US
dc.subject.keywordmolecular jackhammersen_US
dc.subject.keywordstructure-activity relationshipsen_US
dc.subject.keywordvibronic-driven actionen_US
dc.titleDivergent Syntheses of Near-Infrared Light-Activated Molecular Jackhammers for Cancer Cell Eradicationen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpublisher versionen_US
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