Cell-penetrating γ-peptide/antimicrobial undecapeptide conjugates with anticancer activity

Rosés, Cristina; Carbajo, Daniel; Sanclimens, Glòria; Farrera‐Sinfreu, Josep; Blancafort, Adriana; Oliveras, Glòria; Cirac, Anna D.; Bardajı́, Eduard; Puig, Teresa; Planas, Marta; Feliu, Lidia; Alberício, Fernando; Royo, Míriam

doi:10.1016/j.tet.2012.02.003

Cited by 14 publications

(6 citation statements)

References 46 publications

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“…Recent synthesis of truncated fragments of antibacterial peptides such as epinecidin-8 and pardaxin-6 showed higher tumoricidal activity against human epithelial carcinoma (HeLa) and fibrosarcoma (HT-1080) cell lines [118]. The combination of cell-penetrating- γ peptide, PEG-1, with antimicrobial undecapeptides showed efficient anticancer properties against MDA-MB-231 human breast cancer cells [119]. Certain AMPs such as pexiganan MSI-78, citropin 1.1, protegrin 1, synthetic lipopeptide, and N- α -palmitoyl-L-lysine–L-lysine amide (Pal-Lys-Lys-NH 2 ) showed cytotoxic activity against U937 histiocytic cell line.…”

Section: Multidimensional Properties Of Ampsmentioning

confidence: 99%

Antimicrobial Peptides: Versatile Biological Properties

Muthuirulan

Gunasekaran

Rajendhran

2013

International Journal of Peptides

228

153

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Antimicrobial peptides are diverse group of biologically active molecules with multidimensional properties. In recent past, a wide variety of AMPs with diverse structures have been reported from different sources such as plants, animals, mammals, and microorganisms. The presence of unusual amino acids and structural motifs in AMPs confers unique structural properties to the peptide that attribute for their specific mode of action. The ability of these active AMPs to act as multifunctional effector molecules such as signalling molecule, immune modulators, mitogen, antitumor, and contraceptive agent makes it an interesting candidate to study every aspect of their structural and biological properties for prophylactic and therapeutic applications. In addition, easy cloning and recombinant expression of AMPs in heterologous plant host systems provided a pipeline for production of disease resistant transgenic plants. Besides these properties, AMPs were also used as drug delivery vectors to deliver cell impermeable drugs to cell interior. The present review focuses on the diversity and broad spectrum antimicrobial activity of AMPs along with its multidimensional properties that could be exploited for the application of these bioactive peptides as a potential and promising drug candidate in pharmaceutical industries.

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Section: Multidimensional Properties Of Ampsmentioning

confidence: 99%

Antimicrobial Peptides: Versatile Biological Properties

Muthuirulan

Gunasekaran

Rajendhran

2013

International Journal of Peptides

228

153

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“…By using conjugates of g-peptides with antimicrobial peptides, antimicrobial peptides were effectively delivered into the cells and anticancer activity was enhanced. [19] This study demonstrated that cellpenetrating g-peptide foldamersw ereu seful for the cellular transport of therapeutic peptides. a,a-Disubstituted a-Amino Acids a,a-Disubstituted a-aminoa cids (dAAs) have an additional alkyl substituent at the a positiono fa na-aminoa cid instead of ah ydrogena tom.…”

Section: G-amino Acidsmentioning

confidence: 84%

“…Cell‐penetrating γ‐peptide foldamers were also applied as drug‐delivery tools. By using conjugates of γ‐peptides with antimicrobial peptides, antimicrobial peptides were effectively delivered into the cells and anticancer activity was enhanced . This study demonstrated that cell‐penetrating γ‐peptide foldamers were useful for the cellular transport of therapeutic peptides.…”

Section: γ‐Amino Acidsmentioning

confidence: 99%

Cell‐Penetrating Peptide Foldamers: Drug‐Delivery Tools

Oba

2019

ChemBioChem

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Highly efficient drug‐delivery tools for membrane‐impermeable compounds, proteins, and nucleic acids in living cells are useful in the fields of chemical biology and drug discovery, and such tools have been widely studied. One strategy in the development of novel drug‐delivery tools is to utilize cell‐penetrating peptide (CPP) foldamers. CPP foldamers are folded oligopeptides that possess cell membrane permeability. In recent decades, a wide variety of CPP foldamers have been reported by many groups. Herein, CPP foldamers are introduced and discussed from the viewpoints of component monomers (amino acids) and their application as drug‐delivery tools.

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“…[57] Moreover, γ-peptides containing αguanidino-cis-γ-amino-Pro residues exhibited potent cell-membrane permeability via passive diffusion. [58] γ-Peptides also display resistance to digestive enzymes, such as trypsin and the enzymes present in human serum, suggesting that they could be promising DDS carriers.…”

Section: β-Peptidesmentioning

confidence: 99%

“…[1][2][3][4][5] Most CPPs are able to deliver hydrophilic molecules, such as drugs, peptides, proteins, and DNA, into cells. [6,7] The first reported CPP was the Tat peptide (derived from the transcription protein of HIV-1, positions [48][49][50][51][52][53][54][55][56][57][58][59][60], and a variety of CPPs based on the Tat-peptide sequence have since been developed. [8,9] Most of these peptides contain cationic amino acid residues, such as arginine (Arg) or lysine (Lys), in their sequence, and in particular the guanidine moiety of Arg appears to play a crucial role in the cell entry process.…”

Section: Introductionmentioning

confidence: 99%

De Novo Design of Cell‐Penetrating Foldamers

Yokoo

Misawa

Demizu

2020

The Chemical Record

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Cell‐penetrating peptides (CPPs) have gained much attention as carriers of hydrophilic molecules, such as drugs, peptides, and nucleic acids, into cells. CPPs are mainly composed of cationic amino acid residues, which play an important role in their intracellular uptake via interactions with acidic groups on cell surfaces. In addition, the secondary structures of CPPs also affect their cell‐membrane permeability. Based on this knowledge, a variety of cell‐penetrating foldamers (oligomers that form organized secondary structures) have been developed to date. In this account, we describe recent attempts to develop cell‐penetrating foldamers containing various building blocks, and their application as DDS carriers.

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Cell-penetrating γ-peptide/antimicrobial undecapeptide conjugates with anticancer activity

Cited by 14 publications

References 46 publications

Antimicrobial Peptides: Versatile Biological Properties

Antimicrobial Peptides: Versatile Biological Properties

Cell‐Penetrating Peptide Foldamers: Drug‐Delivery Tools

De Novo Design of Cell‐Penetrating Foldamers

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