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Fluorescent and Photosensitizing Conjugates of Cell-Penetrating Peptide TAT(47-57): Design, Microwave-Assisted Synthesis at 60 °C, and Properties
Nancy M Okuda-Shinagawa
1
,
Yulia E Moskalenko
1
,
Helena C Junqueira
1
,
Mauricio S. Baptista
1
,
Carlos M. Marques
1, 2
,
Maria Terêsa Machini
1
Тип публикации: Journal Article
Дата публикации: 2017-11-20
scimago Q1
wos Q2
БС1
SJR: 0.773
CiteScore: 7.1
Impact factor: 4.3
ISSN: 24701343
PubMed ID:
30023576
General Chemistry
General Chemical Engineering
Краткое описание
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 conjugates but also that the minimal inhibitory concentration was slightly reduced for cells incubated with PS-bearing conjugate Chk-PEG6-TAT(47-57)-NH2. Overall, these results indicated that the synthetic approach on-resin assisted by microwaves at 60 °C is simple, straightforward, selective, metal-free, sufficiently fast, cleaner, and more cost-effective than those previously used for preparing this type of macromolecule. Furthermore, such new data show that microwaves at 60 °C and/or conjugation did not harm the integrity of the conjugates' constituents. Therefore, FAM-GG-TAT(47-57)-NH2, FAM-PEG6-TAT(47-57)-NH2, and Chk-PEG6-TAT(47-57)-NH2 have high potential for practical applications in biochemistry, biophysics, and therapeutics.
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International Journal of Peptide Research and Therapeutics
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Journal of Inorganic Biochemistry
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Results in Chemistry
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European Journal of Medicinal Chemistry
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Okuda-Shinagawa N. M. et al. Fluorescent and Photosensitizing Conjugates of Cell-Penetrating Peptide TAT(47-57): Design, Microwave-Assisted Synthesis at 60 °C, and Properties // ACS Omega. 2017. Vol. 2. No. 11. pp. 8156-8166.
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Okuda-Shinagawa N. M., Moskalenko Y. E., Junqueira H. C., Baptista M. S., Marques C. M., Machini M. T. Fluorescent and Photosensitizing Conjugates of Cell-Penetrating Peptide TAT(47-57): Design, Microwave-Assisted Synthesis at 60 °C, and Properties // ACS Omega. 2017. Vol. 2. No. 11. pp. 8156-8166.
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TY - JOUR
DO - 10.1021/acsomega.7b01127
UR - https://doi.org/10.1021/acsomega.7b01127
TI - Fluorescent and Photosensitizing Conjugates of Cell-Penetrating Peptide TAT(47-57): Design, Microwave-Assisted Synthesis at 60 °C, and Properties
T2 - ACS Omega
AU - Okuda-Shinagawa, Nancy M
AU - Moskalenko, Yulia E
AU - Junqueira, Helena C
AU - Baptista, Mauricio S.
AU - Marques, Carlos M.
AU - Machini, Maria Terêsa
PY - 2017
DA - 2017/11/20
PB - American Chemical Society (ACS)
SP - 8156-8166
IS - 11
VL - 2
PMID - 30023576
SN - 2470-1343
ER -
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@article{2017_Okuda-Shinagawa,
author = {Nancy M Okuda-Shinagawa and Yulia E Moskalenko and Helena C Junqueira and Mauricio S. Baptista and Carlos M. Marques and Maria Terêsa Machini},
title = {Fluorescent and Photosensitizing Conjugates of Cell-Penetrating Peptide TAT(47-57): Design, Microwave-Assisted Synthesis at 60 °C, and Properties},
journal = {ACS Omega},
year = {2017},
volume = {2},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acsomega.7b01127},
number = {11},
pages = {8156--8166},
doi = {10.1021/acsomega.7b01127}
}
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Okuda-Shinagawa, Nancy M., et al. “Fluorescent and Photosensitizing Conjugates of Cell-Penetrating Peptide TAT(47-57): Design, Microwave-Assisted Synthesis at 60 °C, and Properties.” ACS Omega, vol. 2, no. 11, Nov. 2017, pp. 8156-8166. https://doi.org/10.1021/acsomega.7b01127.