New Sensitizers Developed on a Methylpheophorbide a Platform for Photodynamic Therapy: Synthesis, Singlet Oxygen Generation and Modeling of Passive Membrane Transport
- *Corresponding Author:
- Kustov AV
United Physico-chemical center
Krestov institute of solution chemistry of russian academy of sciences
Akademicheskaya st., 1, 153045, Ivanovo, Russian federation
E-mail: [email protected]
Received date: May 12, 2016; Accepted date: May 23, 2016; Published date: May 25, 2016
Citation: Kustov AV, Belykh DV, Startseva OM, Kruchin SO, Venediktov EA, et al. (2016) New Sensitizers Developed on a Methylpheophorbide a Platform for Photodynamic Therapy: Synthesis, Singlet Oxygen Generation and Modeling of Passive Membrane Transport. Pharm Anal Acta 7: 480. doi:10.4172/2153-2435.1000480
Copyright: © 2016 Kustov AV, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
This study focuses on the behavior of new potential sensitizers for photodynamic therapy of cancer developed on a chlorophyll a platform. Pheophorbide a 17-(3) methylester and its two glycol derivatives have been synthesized from chlorophyll and identified via visible, UV-, NMR- and MS-spectra. The behavior of photosensitizers in solutions has been studied with various experimental techniques. They are found to generate singlet oxygen with a sufficient quantum yield and reveal a tendency to effectively penetrate into cell membranes due to high lipophilicity. Thermodynamic analysis indicates that the sensitizer transfer from a water-like to a lipid-like medium is controlled by a large and negative enthalpic term excepting the case of the most polar solute, where for phosphate saline buffer the favorable entropic term dominates. Our study highlights the important feature dealing with the temperature dependence of partition coefficients between saline buffer and 1-octanol which is found to be surprisingly strong for hydrophobic solutes and temperature independent for the species containing both H-donor and H-acceptor groups.