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Theoretical determination of two-photon absorption in biologically relevant pterin derivatives

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  • Published: 27 October 2020
  • volume 19, pages 1538–1547 (2020)
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Theoretical determination of two-photon absorption in biologically relevant pterin derivatives
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  • Thomas Malcomson  ORCID: orcid.org/0000-0002-1401-79761 &
  • Martin J. Paterson  ORCID: orcid.org/0000-0002-0012-974X2 

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Abstract

Given the prevalence of fluorescence spectroscopy in biological systems, and the prevalence of pterin derivatives throughout biological systems, presented here is an assessment of the two-photon absorption spectroscopy as it applies to a range of the most commonly studied pterin derivatives. QR-CAMB3LYP//ccpVTZ calculations suggest that the use of two-photon spectroscopic methods would enable a more capable differentiation between closely related derivatives in comparison to the one-photon spectra, which show minimal qualitative deviation. Study of short tail derivatives shows that, in most cases, two-photon accessible states solely involve the π* LUMO as the particle orbital, with biopterin, neopterin, and 6-(hydroxymethyl)pterin presenting exceptional potential for targetting. Investigation of derivatives in which the tail contains an aromatic ring resulted in the observation of a series of two-photon accessible states involving charge transfer from the tail to the pterin moiety, the cross sections of which are highly dependent on the adoption of a planar geometry. The observation of these states presents a novel method for tracking the substitution of biologically important molecules such as folic acid and 5-methenyltetrahydrofolylpolyglutamate.

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  1. Department of Chemistry, Lancaster University, Lancaster, LA1 4YB, UK

    Thomas Malcomson

  2. School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK

    Martin J. Paterson

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Malcomson, T., Paterson, M.J. Theoretical determination of two-photon absorption in biologically relevant pterin derivatives. Photochem Photobiol Sci 19, 1538–1547 (2020). https://doi.org/10.1039/d0pp00255k

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  • Received: 31 July 2020

  • Accepted: 23 September 2020

  • Published: 27 October 2020

  • Issue Date: November 2020

  • DOI: https://doi.org/10.1039/d0pp00255k

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