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Full text release has been delayed at the author's request until May 13, 2026

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Creating the Perfect Photoresponsive Prodrug: Comparing SPAAC Fluorophore Conjugated Platinum Chemotherapy

Cheline, May Marie
http://orcid.org/0000-0001-6768-9197
http://rave.ohiolink.edu/etdc/view?acc_num=kent1714340273099747

Abstract Details

2024, MS, Kent State University, College of Arts and Sciences / Department of Chemistry and Biochemistry.
Platinum-based photoresponsive chemotherapeutic agents have shown promising capabilities due to their ability to be spatiotemporally controlled by light. Within photoresponsive chemotherapeutics, photoinduced electron transfer - from a photoresponsive ligand to the metal center - is necessary in both photoreductive and photolabile mechanisms. In this thesis, we have synthesized, characterized, and analyzed two fluorescein-conjugated platinum species, one with a Pt(IV) photoreductive scaffold and the other with a Pt(II) photolabile compound using click chemistry (strain-promoted azide-alkyne cycloadditions). We then tested these compounds to determine if they underwent photoinduced electron transfer when irradiated. While the Pt(II) photolabile complex did not demonstrate photolabile properties, indicating the complex likely did not undergo photoinduced electron transfer, the Pt(IV) complex demonstrated photoreduction; thus, demonstrating the Pt(IV) complex underwent photoinduced electron transfer upon irradiation. We then tested the effects of acetate modification of the fluorescein moiety of the Pt(IV) species in vitro. The acetate-modified Pt(IV) photoactivatable chemotherapeutic outperformed its unmodified counterpart in cellular uptake, giving it better cytotoxicity when irradiated. These findings demonstrate Pt(IV) photoreductive species and acetate-modified photoresponsive compounds as more suitable approaches compared to Pt(II) photolabile compounds and acetate-unmodified photoresponsive chemotherapeutics for future photoresponsive chemotherapeutic research.
Yaorong Zheng (Advisor)
Songping Huang (Committee Member)
Min-Ho Kim (Committee Member)
78 p.
Biochemistry; Chemistry; Inorganic Chemistry
photoactivatable chemotherapy; SPAAC; click chemistry; strain-promoted azide-alkyne cycloaddition; photolabile; Pt(IV); photoreduction; Pt(II); acetate modification; lipophilic modification; photoinduced electron transfer; photoresponsive; PACT; photoinduced ligand exchange; photoinduced reductive elimination; A2780; MDA-MB-231;

Recommended Citations

Citations

  • Cheline, M. M. (2024). Creating the Perfect Photoresponsive Prodrug: Comparing SPAAC Fluorophore Conjugated Platinum Chemotherapy [Master's thesis, Kent State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=kent1714340273099747

    APA Style (7th edition)

  • Cheline, May. Creating the Perfect Photoresponsive Prodrug: Comparing SPAAC Fluorophore Conjugated Platinum Chemotherapy. 2024. Kent State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=kent1714340273099747.

    MLA Style (8th edition)

  • Cheline, May. "Creating the Perfect Photoresponsive Prodrug: Comparing SPAAC Fluorophore Conjugated Platinum Chemotherapy." Master's thesis, Kent State University, 2024. http://rave.ohiolink.edu/etdc/view?acc_num=kent1714340273099747

    Chicago Manual of Style (17th edition)

kent1714340273099747
© 2024, some rights reserved.Creative Commons License Creating the Perfect Photoresponsive Prodrug: Comparing SPAAC Fluorophore Conjugated Platinum Chemotherapy by May Marie Cheline is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 Unported License. Based on a work at etd.ohiolink.edu.
This open access ETD is published by Kent State University and OhioLINK.