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肽共轭苝二酰亚胺两亲分子的固相合成及其在光动力疗法中的应用

Solid-Phase Synthesis of Peptide-Conjugated Perylene Diimide Bolaamphiphile and Its Application in Photodynamic Therapy.

作者信息

Kim Young-O, Park Sung-Jun, Jung Byeong Yeon, Jang Hyung-Seok, Choi Seo Keong, Kim Jaehi, Kim Sehoon, Jung Yong Chae, Shin Dong-Sik, Lee Yoon-Sik

机构信息

School of Chemical and Biological Engineering, Seoul National University, Gwanak-gu, Seoul 08826, Republic of Korea.

Multifunctional Structural Composite Center, Institute of Advanced Composite Materials, Korea Institute of Science and Technology (KIST), Wanju-gun 55324, Jeonbuk, Republic of Korea.

出版信息

ACS Omega. 2018 May 31;3(5):5896-5902. doi: 10.1021/acsomega.8b00040.

DOI:10.1021/acsomega.8b00040
PMID:30023928
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6045400/
Abstract

Here, we describe a rapid and efficient synthetic method of peptide-conjugated perylene diimide (P-PDI) using solid-phase peptide synthesis (SPPS). Due to severe insolubility of perylene dianhydride (PDA) as a starting material of perylene diimide (PDI), PDA was initially conjugated with amino acids to obtain soluble PDI derivatives. Target peptides were synthesized on a 2-chlorotrityl chloride resin using the SPPS method and then conjugated with the amino acid-appended PDI. Various conditions such as loading levels, reaction times and solvents were optimized for introducing the peptides to both sides of the amino acid-appended PDI. The final P-PDI was obtained with a maximum yield of 80% in 12 h. Its singlet oxygen-derived phototoxicity on cells was confirmed, which could be applicable to photodynamic therapy.

摘要

在此，我们描述了一种使用固相肽合成（SPPS）快速高效合成肽缀合苝二酰亚胺（P-PDI）的方法。由于苝二酐（PDA）作为苝二酰亚胺（PDI）的起始原料具有严重的不溶性，因此首先将PDA与氨基酸缀合以获得可溶性PDI衍生物。使用SPPS方法在2-氯三苯甲基氯树脂上合成目标肽，然后与附加氨基酸的PDI缀合。对诸如负载量、反应时间和溶剂等各种条件进行了优化，以将肽引入附加氨基酸的PDI的两侧。最终的P-PDI在12小时内以最高80%的产率获得。证实了其对细胞的单线态氧衍生的光毒性，这可应用于光动力疗法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/d973684b3fc2/ao-2018-00040m_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/6f6c04cc10b5/ao-2018-00040m_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/e45e465068d0/ao-2018-00040m_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/1c9f438cff0c/ao-2018-00040m_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/c75af7b6a014/ao-2018-00040m_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/dd91f125fe66/ao-2018-00040m_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/d973684b3fc2/ao-2018-00040m_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/6f6c04cc10b5/ao-2018-00040m_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/e45e465068d0/ao-2018-00040m_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/1c9f438cff0c/ao-2018-00040m_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/c75af7b6a014/ao-2018-00040m_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/dd91f125fe66/ao-2018-00040m_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/277d/6645935/d973684b3fc2/ao-2018-00040m_0004.jpg

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