Conjugation of chlorins with spermine enhances phototoxicity to cancer cells in vitro

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F17%3A43913328" target="_blank" >RIV/60461373:22330/17:43913328 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1016/ijphotobiol.2017.02.012" target="_blank" >http://dx.doi.org/10.1016/ijphotobiol.2017.02.012</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/ijphotobiol.2017.02.012" target="_blank" >10.1016/ijphotobiol.2017.02.012</a>

Result language

angličtina

Original language name

Conjugation of chlorins with spermine enhances phototoxicity to cancer cells in vitro

Original language description

Photodynamic therapy (PDT) is one of the most promising methods of specific cancer treatment. However, commercially available photosensitizers (PSs) show significant drawbacks, such as side toxicity, low penetration ability, low blood solubility, low tumor selectivity etc. In addition, as was shown previously, a conjugation of polyamines with several toxic agents led to an increased toxicity to cancer cells. Here, we synthesized conjugates of two chlorine photosensitizers, purpurin 18 and pheophorbide a, with spermine in natural and Boc-protected form. Using specialized software, we calculated octanol-water partition coefficients for single protonation state (logP) of single PSs and PS/spermine conjugates. We found that the addition of spermine to chlorine PSs shifted the logP towards higher hydrophilicity in comparison to logP of single chlorines. In vitro studies on several cancer cells indicated that conjugation of purpurin 18 with spermine increased its retention in cancer cells. Using various concentrations of this conjugate, we found that lower concentrations (under 02 mu M) of purpurin 18/spermine conjugate launched apoptosis in HeLa cells. This combined with its high phototoxicity makes the purpurin 18/spermine conjugate a promising photosensitizer for PDT. Obtained results might serve as a basis for further studies of this potential third-generation PS on mammalian models in vivo.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10400 - Chemical sciences

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Journal of Photochemistry and Photobiology B: Biology

ISSN

1011-1344

e-ISSN

—

Volume of the periodical

168

Issue of the periodical within the volume

březen 2017

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

10

Pages from-to

175-184

UT code for WoS article

000397689500022

EID of the result in the Scopus database

2-s2.0-85013393674