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Mass Spectrometric Study of Acoustically Levitated Droplet Illuminates Molecular-Level Mechanism of Photodynamic Therapy for Cancer involving Lipid Oxidation

Mu, Chaonan and Wang, Jie and Barraza, Kevin M. and Zhang, Xinxing and Beauchamp, J. L. (2019) Mass Spectrometric Study of Acoustically Levitated Droplet Illuminates Molecular-Level Mechanism of Photodynamic Therapy for Cancer involving Lipid Oxidation. Angewandte Chemie International Edition, 58 (24). pp. 8082-8086. ISSN 1433-7851. http://resolver.caltech.edu/CaltechAUTHORS:20190424-144449221

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Abstract

Even though the general mechanism of photodynamic cancer therapy is known, the details and consequences of the reactions between the photosensitizer‐generated singlet oxygen and substrate molecules remain elusive at the molecular level. Using temoporfin as the photosensitizer, here we combine field‐induced droplet ionization mass spectrometry and acoustic levitation techniques to study the “wall‐less” oxidation reactions of 18:1 cardiolipin and 1‐palmitoyl‐2‐oleoyl‐sn‐glycero‐3‐phospho‐(1′‐rac‐glycerol) (POPG) mediated by singlet oxygen at the air–water interface of levitated water droplets. For both cardiolipin and POPG, every unsaturated oleyl chain is oxidized to an allyl hydroperoxide, which surprisingly is immune to further oxidation. This is attributed to the increased hydrophilicity of the oxidized chain, which attracts it toward the water phase, thereby increasing membrane permeability and eventually triggering cell death.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201902815DOIArticle
ORCID:
AuthorORCID
Barraza, Kevin M.0000-0003-1849-5219
Beauchamp, J. L.0000-0001-8839-4822
Additional Information:© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Manuscript received: March 5, 2019; Accepted manuscript online: April 23, 2019; Version of record online: May 9, 2019. This work was supported by the Beckman Institute at Caltech and by NSF grant CHE-1508825 (J.L.B.). This work is dedicated to the 100th anniversary of Nankai University. The authors declare no conflict of interest.
Funders:
Funding AgencyGrant Number
Caltech Beckman InstituteUNSPECIFIED
NSFCHE-1508825
Subject Keywords:Lipid oxidation; photodynamic therapy; Mass spectrometry; Air-water interface; Acoustic levitation
Record Number:CaltechAUTHORS:20190424-144449221
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20190424-144449221
Official Citation:C. Mu, J. Wang, K. M. Barraza, X. Zhang, J. L. Beauchamp, Angew. Chem. Int. Ed. 2019, 58, 8082; doi: 10.1002/anie.201902815
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:94946
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:24 Apr 2019 21:51
Last Modified:05 Jun 2019 15:53

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