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

ACS Omega
Young-O KimYoon-Sik Lee

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.

References

Mar 17, 1993·Journal of the National Cancer Institute·H I Pass
Apr 1, 1993·The Journal of Dermatologic Surgery and Oncology·S L Kilmer, R R Anderson
Jan 1, 1996·Annual Review of Cell and Developmental Biology·E Ruoslahti
Jun 24, 1998·Journal of the National Cancer Institute·T J DoughertyQ Peng
Jul 29, 1998·Archives of Dermatology·C C DierickxR R Anderson
May 2, 2003·Nature Reviews. Cancer·Dennis E J G J DolmansRakesh K Jain
Aug 19, 2003·Biomaterials·Ulrich HerselHorst Kessler
Jul 23, 2004·Journal of Medicinal Chemistry·Michael R DettyStephen J Wagner
Aug 4, 2004·The Lancet Oncology·Stanley B BrownIan Walker
May 28, 2011·CA: a Cancer Journal for Clinicians·Patrizia AgostinisJakub Golab
Jul 6, 2012·Chemical Communications : Chem Comm·Joseph K GallaherJustin M Hodgkiss
Sep 25, 2012·Chemistry : a European Journal·Changzhun ShaoFrank Würthner
Jan 22, 2013·Dermatologic Surgery : Official Publication for American Society for Dermatologic Surgery [et Al.]·Stephanie D Gan, Emmy M Graber
Jun 21, 2014·The Journal of Physical Chemistry. B·Galen L EakinsJustin M Hodgkiss
Aug 14, 2015·Chemical Reviews·Frank WürthnerDavid Schmidt
Jan 23, 2016·Chemical Society Reviews·Mengmeng SunMeizhen Yin

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Citations

Jul 27, 2021·ACS Biomaterials Science & Engineering·Hyesung LeeSang-Yup Lee
Aug 7, 2021·International Journal of Biological Macromolecules·Farnaz AzadikhahMahnaz Hadizadeh

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Methods Mentioned

BETA
NMR
column chromatography

Software Mentioned

PDI

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