Direct Measurement of the Visible to UV Photodissociation Processes for the PhotoCORM TryptoCORM

TY - JOUR

T1 - Direct Measurement of the Visible to UV Photodissociation Processes for the PhotoCORM TryptoCORM

AU - Dessent, Caroline Elizabeth Helen

AU - Cercola, Rosaria

AU - Wong, Natalie

AU - Lynam, Jason Martin

AU - Fairlamb, Ian James Stewart

AU - Hammarback, Anders

AU - Garand, Etienne

AU - Fischer, Kaitlyn

AU - Sherman, Summer

PY - 2020/4/10

Y1 - 2020/4/10

N2 - PhotoCORMs are light‐triggered compounds that release CO for medical applications. Here, we apply laser spectroscopy in the gas phase to TryptoCORM, a known photoCORM that has been shown to destroy Escherichia coli upon visible‐light activation. Our experiments allow us to map TryptoCORM’s photochemistry across a wide wavelength range by using novel laser‐interfaced mass spectrometry (LIMS). LIMS provides the intrinsic absorption spectrum of the photoCORM along with the production spectra of all of its ionic photoproducts for the first time. Importantly, the photoproduct spectra directly reveal the optimum wavelengths for maximizing CO ejection, and the extent to which CO ejection is compromised at redder wavelengths. A series of comparative studies were performed on TryptoCORM‐CH3CN which exists in dynamic equilibrium with TryptoCORM in solution. Our measurements allow us to conclude that the presence of the labile CH3CN facilitates CO release over a wider wavelength range. This work demonstrates the potential of LIMS as a new methodology for assessing active agent release ( e.g. CO, NO, H2S) from light‐activated prodrugs.

AB - PhotoCORMs are light‐triggered compounds that release CO for medical applications. Here, we apply laser spectroscopy in the gas phase to TryptoCORM, a known photoCORM that has been shown to destroy Escherichia coli upon visible‐light activation. Our experiments allow us to map TryptoCORM’s photochemistry across a wide wavelength range by using novel laser‐interfaced mass spectrometry (LIMS). LIMS provides the intrinsic absorption spectrum of the photoCORM along with the production spectra of all of its ionic photoproducts for the first time. Importantly, the photoproduct spectra directly reveal the optimum wavelengths for maximizing CO ejection, and the extent to which CO ejection is compromised at redder wavelengths. A series of comparative studies were performed on TryptoCORM‐CH3CN which exists in dynamic equilibrium with TryptoCORM in solution. Our measurements allow us to conclude that the presence of the labile CH3CN facilitates CO release over a wider wavelength range. This work demonstrates the potential of LIMS as a new methodology for assessing active agent release ( e.g. CO, NO, H2S) from light‐activated prodrugs.

KW - CORM

KW - PhotoCORM

KW - Laser Photochemistry

KW - Antimicrobial

KW - transition metal complexes

U2 - 10.1002/chem.202001077

DO - 10.1002/chem.202001077

M3 - Article

SN - 0947-6539

JO - Chemistry : A European Journal

JF - Chemistry : A European Journal

ER -