Two-Photon-Induced CO-Releasing Molecules as Molecular Logic Systems in Solution, Polymers, and Cells

Vadde Ramu; Gandra Upendar Reddy; Jingjing Liu; Patrick Hoffmann; Rudrakant Sollapur; Ralf Wyrwa; Stephan Kupfer; Christian Spielmann; Sylvestre Bonnet; Ute Neugebauer; Alexander Schiller

doi:10.1002/chem.201901396

Two-Photon-Induced CO-Releasing Molecules as Molecular Logic Systems in Solution, Polymers, and Cells

Chemistry. 2019 Jun 26;25(36):8453-8458. doi: 10.1002/chem.201901396. Epub 2019 May 20.

Authors

Vadde Ramu¹, Gandra Upendar Reddy¹, Jingjing Liu¹, Patrick Hoffmann^{2

3}, Rudrakant Sollapur⁴, Ralf Wyrwa⁵, Stephan Kupfer⁶, Christian Spielmann⁴, Sylvestre Bonnet⁷, Ute Neugebauer^{2

6

3}, Alexander Schiller¹

Affiliations

¹ Institute for Inorganic and Analytical Chemistry (IAAC), Friedrich Schiller University Jena, Humboldtstr. 8, 07743, Jena, Germany.
² Center for Sepsis Control and Care (CSCC), Jena University Hospital, Am Klinikum 1, 07747, Jena, Germany.
³ Leibniz Institute of Photonic Technology, Albert-Einstein-Str. 9, 07745, Jena, Germany.
⁴ Institute of Optics and Quantum Electronics, Friedrich Schiller University Jena, Max Wien Platz 1, 07743, Jena, Germany.
⁵ INNOVENT e.V., Biomaterials Department, Prüssingstraße 27B, 07745, Jena, Germany.
⁶ Institute for Physical Chemistry (IPC) and Abbe Center of Photonics (ACP), Friedrich Schiller University Jena, Helmholtzweg 4, 07743, Jena, Germany.
⁷ Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, 2300, RA, Leiden, The Netherlands.

PMID: 30980425
DOI: 10.1002/chem.201901396

Abstract

Phototherapeutic applications of carbon monoxide (CO)-releasing molecules are limited because they require harmful UV and blue light for activation. We describe two-photon excitation with NIR light (800 nm)-induced CO-release from two Mn^I tricarbonyl complexes bearing 1,8-naphthalimide units (1, 2). Complex 2 behaves as a logic OR gate in solution, nonwovens, and in HeLa cells. CO release, indicated by fluorescence enhancement, was detected in solution, nonwoven, and HeLa cells by single- (405 nm) and two-photon (800 nm) excitation. The photophysical properties of 1 and 2 have been measured and supported by DFT and TDDFT quantum chemical calculations. Both photoCORMs are stable in the dark in solution and noncytotoxic, leading to promising applications as phototherapeutics with NIR light.

Keywords: immobilization; logic gates; low cytotoxicity; nonwoven fabric materials; two-photon CORMs.

Abstract

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