@article{siwawannapong_diers_magdaong_nalaoh_kirmaier_lindsey_holten_bocian_2024, title={Extension of nature's NIR-I chromophore into the NIR-II region}, volume={5}, ISSN={["1463-9084"]}, DOI={10.1039/d4cp00779d}, abstractNote={The development of chromophores that absorb in the near-infrared (NIR) region beyond 1000 nm underpins numerous applications in medical and energy sciences, yet also presents substantial challenges to molecular design and chemical synthesis. Here, the core bacteriochlorin chromophore of nature's NIR absorbers, bacteriochlorophylls, has been adapted and tailored by annulation in an effort to achieve absorption in the NIR-II region. The resulting bacteriochlorin, Phen2,1-BC, contains two annulated naphthalene groups spanning}, journal={PHYSICAL CHEMISTRY CHEMICAL PHYSICS}, author={Siwawannapong, Kittipan and Diers, James R. and Magdaong, Nikki Cecil M. and Nalaoh, Phattananawee and Kirmaier, Christine and Lindsey, Jonathan S. and Holten, Dewey and Bocian, David F.}, year={2024}, month={May} } @article{siwawannapong_nemeth_melander_rong_davis_taniguchi_carpenter_lindsey_melander_2022, title={Simple Dipyrrin Analogues of Prodigiosin for Use as Colistin Adjuvants}, volume={7}, ISSN={["1860-7187"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-85133558458&partnerID=MN8TOARS}, DOI={10.1002/cmdc.202200286}, abstractNote={Abstract}, number={16}, journal={CHEMMEDCHEM}, author={Siwawannapong, Kittipan and Nemeth, Ansley M. and Melander, Roberta J. and Rong, Jie and Davis, Jonathan R. and Taniguchi, Masahiko and Carpenter, Morgan E. and Lindsey, Jonathan S. and Melander, Christian}, year={2022}, month={Jul} } @article{wu_dou_nguyen_eppley_siwawannapong_zhang_lindsey_2022, title={Tailoring the AIE Chromogen 2-(2-Hydroxyphenyl)benzothiazole for Use in Enzyme-Triggered Molecular Brachytherapy}, volume={27}, ISSN={["1420-3049"]}, DOI={10.3390/molecules27248682}, abstractNote={A targeted strategy for treating cancer is antibody-directed enzyme prodrug therapy, where the enzyme attached to the antibody causes conversion of an inactive small-molecule prodrug into an active drug. A limitation may be the diffusion of the active drug away from the antibody target site. A related strategy with radiotherapeutics entails enzymatically promoted conversion of a soluble to insoluble radiotherapeutic agent, thereby immobilizing the latter at the target site. Such a molecular brachytherapy has been scarcely investigated. In distinct research, the advent of molecular designs for aggregation-induced emission (AIE) suggests translational use in molecular brachytherapy. Here, several 2-(2-hydroxyphenyl)benzothiazole substrates that readily aggregate in aqueous solution (and afford AIE) were elaborated in this regard. In particular, (1) the 2-(2-hydroxyphenyl) unit was derivatized to bear a pegylated phosphodiester that imparts water solubility yet undergoes enzymatic cleavage, and (2) a p-phenol unit was attached to the benzo moiety to provide a reactive site for final-step iodination (here examined with natural abundance iodide). The pegylated phosphodiester-iodinated benzothiazole undergoes conversion from aqueous-soluble to aqueous-insoluble upon treatment with a phosphatase or phosphodiesterase. The aggregation is essential to molecular brachytherapy, whereas the induced emission of AIE is not essential but provides a convenient basis for research development. Altogether, 21 compounds were synthesized (18 new, 3 known via new routes). Taken together, blending biomedical strategies of enzyme prodrug therapy with materials chemistry concerning substances that undergo AIE may comprise a step forward on the long road toward molecular brachytherapy.}, number={24}, journal={MOLECULES}, author={Wu, Zhiyuan and Dou, Jinghuai and Nguyen, Kathy-Uyen and Eppley, Jayden C. and Siwawannapong, Kittipan and Zhang, Yunlong and Lindsey, Jonathan S.}, year={2022}, month={Dec} }