TAT (47-57) peptide – Cell-penetrating peptide
TAT (47-57) peptide, also known as HIV-1 TAT protein, is the most characterized fragment of the HIV transactivator protein (TAT). TAT (47-57) peptide was show to be a cell-penetrating peptide (CPP). TAT (47-57) is an arginine-rich peptide which directly penetrates plasma membrane and stabilized DNA. TAT (47-57) has the ability to translocate the plasma membrane and facilitate the delivery of various cargoes such as protein, peptide, antibodies, and liposomes. It represents an important tool to increase the biodistribution of drugs.
|Sequence : YGRKKRRQRRR|
|MW : 1 559.89 Da (C64H118N32O14)|
|Purity : > 95%|
|Counter-Ion : TFA Salts (see option TFA removal)|
|Delivery format : Freeze dried in propylene 2mL microtubes|
|Other names : 191936-91-1, HIV-1 Tat protein (47-57) ; tat peptide (47-57), Human immunodeficiency virus 1 ; Tat protein (47-57), HIV-1|
|Peptide Solubility Guideline|
|Bulk peptide quantities available|
|Peptide||Product catalog 1||Size 1||Price 1 € HT||Product catalog 2||Size 2||Price 2 € HT|
|TAT (47-57)||SB013-1MG||1 mg||88||SB013-5*1MG||5×1 mg||308|
|FAM-TAT (47-57)||SB014-1MG||1 mg||198||SB014-5*1MG||5×1 mg||693|
|Cys-TAT (47-57)||SB015-1MG||1 mg||88||SB015-5*1MG||5×1 mg||308|
|TAMRA-TAT (47-57)||SB016-1MG||1 mg||220||SB016-5*1MG||5×1 mg||770|
|Alcyne-TAT (47-57)||SB017-1MG||1 mg||110||SB017-5*1MG||5×1 mg||385|
|Alcyne-FAM-TAT (47-57)||SB018-05MG||0.5 mg||165||SB018-1MG||1 mg||275|
Okuda-Shinagawa NM, Moskalenko YE, Junqueira HC, Baptista MS, Marques CM, Machini MT. ACS Omega (2017)
Fluorescent and Photosensitizing Conjugates of Cell-Penetrating Peptide TAT(47-57): Design, Microwave-Assisted Synthesis at 60 °C, and Properties
BACKGROUND: 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.
METHOD: 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.
RESULTS: 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.
CONCLUSION: 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.