A <scp>d</scp>-Peptide Ligand of Integrins for Simultaneously Targeting Angiogenic Blood Vasculature and Glioma Cells

Ren, Yachao; Zhan, Changyou; Gao, Jie; Zhang, Mingfei; Wei, Xiaoli; Liu, Zining; Lu, Weiyue

doi:10.1021/acs.molpharmaceut.7b00944

Cited by 14 publications

(9 citation statements)

References 51 publications

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“…Compared to bradykinin, its retroinverso analog is found to have better blood‐brain barrier permeability and higher affinity for target receptor BK type 2 (Su et al., ). Similarly, D VS is a retroinverso analog of VS peptide which has higher stability and exceptional efficacy in targeting glioma cells by binding to integrins (Li et al., ; Ren et al., ; Su et al., ). Retroinverso C‐end rule (CendR) peptide D(RPPREGR) has been used to targeted delivery of a gene to glioma cells.…”

Section: Experimental Attempts Of Mimetics Using Retroinverso and Modmentioning

confidence: 99%

Peptide and protein mimetics by retro and retroinverso analogs

Rai

2019

Chem Biol Drug Des

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Retroinverso analog of a natural polypeptide can sometimes mimic the structure and function of the natural peptide. The additional advantage of using retroinverso analog is that it is resistant to proteolysis. The retroinverso analogs have peptide sequence in reverse direction with respect to natural peptide and also have chirality of amino acid inverted from L to D. The D amino acids cannot be recognized by common proteases of the body; therefore, these peptides will not be degraded easily and have a longer‐lasting effect as vaccine and inhibitor drugs. There have been many contested propositions about the geometric relationship between a peptide and its retro, inverso, or retroinverso analog. A retroinverso analog sometimes fails to adopt the structure that can mimic the function of the natural peptide. In such cases, partial retroinverso analog and other modifications can help in achieving the desired structure and function. Here, we review the theory, major experimental attempts, prediction methods, and alternative strategies related to retroinverso peptidomimetics.

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Section: Experimental Attempts Of Mimetics Using Retroinverso and Modmentioning

confidence: 99%

Peptide and protein mimetics by retro and retroinverso analogs

Rai

2019

Chem Biol Drug Des

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“…The peptide VS (Table 1) selected through the screening of a phage display library, also showed high binding affinity towards integrins, in particular against α 6 β 1 and α v β 3 . The RI analogue [52] was designed, prepared and tested against glioblastoma multiforme (GBM), the most common and lethal tumor of the central nervous system [53]. Specifically, the RI variant of VS conjugated with PEG-PLA (poly-lactic acid) was used to prepare micelles which efficiently encapsulated doxorubicin (DOX), penetrated the tumor mass, and reduced its volume more efficiently compared to the control, the free drug, or other micelle formulations.…”

Section: Anticancer Applications-diagnosticmentioning

confidence: 99%

Recent Applications of Retro-Inverso Peptides

Doti

Mardirossian

Sandomenico

et al. 2021

IJMS

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Natural and de novo designed peptides are gaining an ever-growing interest as drugs against several diseases. Their use is however limited by the intrinsic low bioavailability and poor stability. To overcome these issues retro-inverso analogues have been investigated for decades as more stable surrogates of peptides composed of natural amino acids. Retro-inverso peptides possess reversed sequences and chirality compared to the parent molecules maintaining at the same time an identical array of side chains and in some cases similar structure. The inverted chirality renders them less prone to degradation by endogenous proteases conferring enhanced half-lives and an increased potential as new drugs. However, given their general incapability to adopt the 3D structure of the parent peptides their application should be careful evaluated and investigated case by case. Here, we review the application of retro-inverso peptides in anticancer therapies, in immunology, in neurodegenerative diseases, and as antimicrobials, analyzing pros and cons of this interesting subclass of molecules.

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“…An even more compelling proof of the higher efficacy of retro-enantio peptides for brain tumor targeting was provided with a nanotherapy targeted with a retro-enantio version of VS peptide (VSWFSRHRYSPFAVS) [43]. VS targets α 6 β 1 integrins, which are upregulated in glioma cells, and α v β 3 integrins, which are overexpressed in cancer cells and neovasculature.…”

Section: Enantio/retro-enantio Targeting Peptidesmentioning

confidence: 99%

Protease-Resistant Peptides for Targeting and Intracellular Delivery of Therapeutics

et al. 2021

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Peptides show high promise in the targeting and intracellular delivery of next-generation bio- and nano-therapeutics. However, the proteolytic susceptibility of peptides is one of the major limitations of their activity in biological environments. Numerous strategies have been devised to chemically enhance the resistance of peptides to proteolysis, ranging from N- and C-termini protection to cyclization, and including backbone modification, incorporation of amino acids with non-canonical side chains and conjugation. Since conjugation of nanocarriers or other cargoes to peptides for targeting and cell penetration may already provide some degree of shielding, the question arises about the relevance of using protease-resistant sequences for these applications. Aiming to answer this question, here we provide a critical review on protease-resistant targeting peptides and cell-penetrating peptides (CPPs). Two main approaches have been used on these classes of peptides: enantio/retro-enantio isomerization and cyclization. On one hand, enantio/retro-enantio isomerization has been shown to provide a clear enhancement in peptide efficiency with respect to parent L-amino acid peptides, especially when applied to peptides for drug delivery to the brain. On the other hand, cyclization also clearly increases peptide transport capacity, although contribution from enhanced protease resistance or affinity is often not dissected. Overall, we conclude that although conjugation often offers some degree of protection to proteolysis in targeting peptides and CPPs, modification of peptide sequences to further enhance protease resistance can greatly increase homing and transport efficiency.

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A d-Peptide Ligand of Integrins for Simultaneously Targeting Angiogenic Blood Vasculature and Glioma Cells

Cited by 14 publications

References 51 publications

Peptide and protein mimetics by retro and retroinverso analogs

Peptide and protein mimetics by retro and retroinverso analogs

Recent Applications of Retro-Inverso Peptides

Protease-Resistant Peptides for Targeting and Intracellular Delivery of Therapeutics

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