Fluorescent and Photosensitizing Conjugates of Cell-Penetrating Peptide TAT(47-57): Design, Microwave-Assisted Synthesis at 60 °C, and Properties

ACS Omega
Nancy M Okuda-ShinagawaM Terêsa Machini

Abstract

Conjugates based on cell-penetrating peptides (CPPs) are scientifically relevant owing to their structural complexity; their ability to enter cells and deliver drugs, labels, antioxidants, bioactive compounds, or DNA fragments; and, consequently, their potential for application in research and biomedicine. In this study, carboxyamidated fluorescently labeled conjugates FAM-GG-TAT(47-57)-NH2 and FAM-PEG6-TAT(47-57)-NH2 and photosensitizer-labeled conjugate Chk-PEG6-TAT(47-57)-NH2 [where TAT(47-57) is the CPP, 5(6)-carboxyfluorescein is the (FAM) fluorophore, chlorin k (Chk) is the photosensitizer, and the dipeptide glycyl-glycine (GG) or hexaethylene glycol (PEG6) is the spacer] were originally designed, prepared, and fully characterized. Practically, all chemical reactions of the synthetic steps (peptide synthesis, spacer incorporation, and conjugation) were microwave-assisted at 60 °C using optimized protocols to give satisfying yields and high-quality products. Detailed analyses of the conjugates using spectrofluorimetry and singlet oxygen detection showed that they display photophysical properties typical of FAM or Chk. Anticandidal activity assays showed that not only this basic property of TAT(47-57) was preserved in the c...Continue Reading

References

Oct 1, 1994·Journal of Photochemistry and Photobiology. B, Biology·M R Hamblin, E L Newman
Sep 1, 1996·Photochemistry and Photobiology·R W Boyle, D Dolphin
Aug 1, 1997·The Journal of Peptide Research : Official Journal of the American Peptide Society·L M Varanda, M T Miranda
Jun 24, 1998·Journal of the National Cancer Institute·T J DoughertyQ Peng
Apr 17, 2001·Antimicrobial Agents and Chemotherapy·H Yan, R E Hancock
Jan 10, 2003·The Journal of Biological Chemistry·Carsten RudolphJoseph Rosenecker
Jan 7, 2004·Advanced Drug Delivery Reviews·G A M S van DongenM B Vrouenraets
Mar 24, 2004·Biochemistry·Per E G ThorénBengt Nordén
Feb 22, 2005·Advanced Drug Delivery Reviews·Hilary BrooksEric Vivès
May 17, 2005·Biochimica Et Biophysica Acta·Sónia Troeira Henriques, Miguel A R B Castanho
Jun 14, 2005·Medicinal Research Reviews·Ferenc HudeczGabriella Csík
Feb 17, 2006·Journal of Medicinal Chemistry·Martha Sibrian-VazquezM Graça H Vicente
May 9, 2006·Biochemical and Biophysical Research Communications·Hyun Jun JungDong Gun Lee
Jul 20, 2006·Bioconjugate Chemistry·Martha Sibrian-VazquezM Graça H Vicente
Oct 5, 2006·Anti-cancer Agents in Medicinal Chemistry·Raphaël SchneiderMuriel Barberi-Heyob
Dec 13, 2006·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Satomi OnoueTakehiko Yajima
Feb 24, 2007·Langmuir : the ACS Journal of Surfaces and Colloids·Aurélien DeniaudJoël Chopineau
Aug 3, 2007·Journal of Drug Targeting·Amit A Kale, Vladimir P Torchilin
Sep 15, 2007·Biochemical and Biophysical Research Communications·Sarah R DennisonDavid A Phoenix
Apr 29, 2008·Biochimica Et Biophysica Acta·Eric VivèsAndré Pèlegrin
Oct 8, 2008·Journal of Medicinal Chemistry·Inder SehgalM Graça H Vicente
Nov 4, 2008·Expert Opinion on Drug Delivery·Stéphane A SibaniRyan F Donnelly
Jul 16, 2009·Bioconjugate Chemistry·Jacob GrunwaldVladimir P Torchilin
Oct 15, 2009·Journal of Peptide Science : an Official Publication of the European Peptide Society·Carina LoffredoM Terêsa Machini Miranda
Oct 29, 2009·Current Topics in Medicinal Chemistry·Mousa Jafari, P Chen
Feb 22, 2011·European Biophysics Journal : EBJ·Katrin Splith, Ines Neundorf
Jun 15, 2011·Free Radical Biology & Medicine·Carla S OliveiraMauricio S Baptista
Oct 26, 2011·Letters in Applied Microbiology·T HolmU Langel
Aug 13, 2013·Organic & Biomolecular Chemistry·Gabriela A EggimannJean-Louis Reymond
Oct 19, 2013·Biochimica Et Biophysica Acta·Igor MeerovichJean-Philippe Pellois
Dec 3, 2013·Journal of Controlled Release : Official Journal of the Controlled Release Society·Feihu WangFang Jin
Feb 25, 2014·ACS Nano·Dana Maria CopoloviciÜlo Langel
Jun 25, 2014·International Journal of Nanomedicine·Lanxia LiuXigang G Leng

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Methods Mentioned

BETA
acylation
fluorescence microscopies
Assay
irradiating

Software Mentioned

Clarity
HyStar

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