Derivatized cyclodextrins as peptidomimetics: Influence on neurite growth

Borrajo, Alison M.P.; Gorin, B. I.; Dostaler, Suzanne M.; Riopelle, Richard J.; Thatcher, Gregory R. J.

doi:10.1016/s0960-894x(97)00180-7

Cited by 10 publications

(10 citation statements)

References 18 publications

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“…The heparin-binding domain of PF4 has been used as a mimic of the heparin-binding domain of fibronectin and shown to promote neurite extension from various types of neurons on 2-dimensional surfaces (22,34). The heparin-binding domain from ATIII was mimicked by Borrajo et al (35), and in the soluble form was found to inhibit neurite extension on polylysine adsorbed to surfaces. However, when itself adsorbed to a surface, this ATIII domain mimic promoted neurite extension.…”

Section: Discussionsupporting

confidence: 83%

“…Furthermore, the neurite outgrowth induced by this domain could be inhibited by the addition of heparin to the cell culture media, digestion with heparitinase, or inhibition of cell proteoglycan synthesis, suggesting that the proteoglycan interacting with this domain was located on the cell surface. Moreover, heparinbinding proteins that are not naturally involved in supporting cell adhesion have also been shown to influence neurite outgrowth, e.g., the chemokine PF4, the anticoagulant protein ATIII, and the chemokine midkine (20,34,35). The heparin-binding domain of PF4 has been used as a mimic of the heparin-binding domain of fibronectin and shown to promote neurite extension from various types of neurons on 2-dimensional surfaces (22,34).…”

Section: Discussionmentioning

confidence: 99%

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Incorporation of heparin‐binding peptides into fibrin gels enhances neurite extension: an example of designer matrices in tissue engineering

Sakiyama

Schense

Hubbell³

1999

FASEB j.

186

130

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The goal of this work was to improve the potential of fibrin to promote nerve regeneration by enzymatically incorporating exogenous neurite-promoting heparin-binding peptides. The effects on neurite extension of four different heparin-binding peptides, derived from the heparin-binding domains of antithrombin III, neural cell adhesion molecule and platelet factor 4, were determined. These exogenous peptides were synthesized as bi-domain peptide chimeras, with the second domain being a substrate for factor XIIIa. This coagulation transglutaminase covalently bound the peptides within the fibrin gel during coagulation. The heparin-binding peptides enhanced the degree of neurite extension from embryonic chick dorsal root ganglia through 3-dimensional fibrin gels, and the extent of enhancement was found to correlate positively with the heparin-binding affinity of the individual domains. The enhancement could be inhibited by competition with soluble heparin, by degradation of cell-surface proteoglycans, and by inhibition of the covalent immobilization of the peptide. These results demonstrate an important potential role for proteoglycan-binding components of the extracellular matrix in neurite extension and suggest that fibrin gels modified with covalently bound heparin-binding peptides could serve as a therapeutic agent to enhance peripheral nerve regeneration through nerve guide tubes. More generally, the results demonstrate that the biological responses to fibrin, the body's natural wound healing matrix, can be dramatically improved by the addition of exogenous bioactive peptides in a manner such that they become immobilized during coagulation.-Sakiyama, S. E., Schense, J. C., Hubbell, J. A. Incorporation of heparin-binding peptides into fibrin gels enhances neurite extension: an example of designer matrices in tissue engineering.

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Section: Discussionsupporting

confidence: 83%

Section: Discussionmentioning

confidence: 99%

Incorporation of heparin‐binding peptides into fibrin gels enhances neurite extension: an example of designer matrices in tissue engineering

Sakiyama

Schense

Hubbell³

1999

FASEB j.

186

130

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“…Aminocyclodextrins (ACDs) are a specific subset of persubstituted CDs, which may be readily prepared by direct amination of per-6-bromo-per-6-deoxy-CD or per-6-iodo-per-6-deoxy-CD ACDs possess an annulus of amino groups in place of the ether oxygens of native CD and a corona of pendant side chains; at neutral pH the presence of the positively charged annulus diminishes the ability of the ACD cavity to include hydrophobic small molecules 18. The ACD scaffold provides ACD derivatives with demonstrated, inherent biological activity 19. Synthesis from the more reactive per-6-iodo-per-6-deoxy-CD was revealed by careful chromatography to yield an intramolecular cross-linked impurity, 20 whereas synthesis via the less reactive per-6-bromo-per-6-deoxy-CD is accomplished in quantitative steps requiring no chromatography (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Click synthesis of estradiol–cyclodextrin conjugates as cell compartment selective estrogens

Kim

Sohn

Wijewickrama

et al. 2010

Bioorganic & Medicinal Chemistry

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Cyclodextrin (CD) is a well known drug carrier and excipient for enhancing aqueous solubility. CDs themselves are anticipated to have low membrane permeability because of relatively high hydrophilicity and molecular weight. CD derivatization with 17-beta estradiol (E 2 ) was explored extensively using a number of different click chemistries and the cell membrane permeability of synthetic CD-E 2 conjugate was explored by cell reporter assays and confocal fluorescence microscopy. In simile with reported dendrimer -E 2 conjugates, CD-E 2 was found to be a stable, extranuclear receptor selective estrogen that penetrated into the cytoplasm.

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“…Series of per(6-amino-6-deoxy)-cyclodextrins 1a -1c and 2a-DAE -2c-DAE have been shown to bind to glycosylaminoglycan sulfates and inhibit growth of neurites [98]. Per(6-guanidino-6-deoxy)-cyclodextrins 6a -6c not only exhibited strong binding to 4-nitrophenyl phosphate (K a 5 10 4 M -1 ) but 6b also promoted condensation of DNA into nanoparticles as determined by atomic force microscopy, confirming strong electrostatic interaction between the biopolymer and the cationic cyclodextrin [42].…”

Section: Inclusion Complexes Of Cationic and Anionic Cyclodextrins Wimentioning

confidence: 99%

Modified Cyclodextrins with Pendant Cationic and Anionic Moieties as Hosts for Highly Stable Inclusion Complexes and Molecular Recognition

Kraus¹

2011

COC

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Cyclodextrins bearing pendant cationic or anionic moieties have been shown to form highly stable inclusion complexes with oppositely charged organic molecules. These charged hosts are also capable of molecular recognition of various organic cations and anions such as nucleotides and other phosphates, sulfates, sulfonates, carboxylates, enantiomers of amino acids, bile acids and many others. This review summarizes work in this field published till the year 2009 including most common synthetic methods for the preparation of charged cyclodextrin derivatives and examples of their applications in bioorganic chemistry and pharmacy.

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Derivatized cyclodextrins as peptidomimetics: Influence on neurite growth

Cited by 10 publications

References 18 publications

Incorporation of heparin‐binding peptides into fibrin gels enhances neurite extension: an example of designer matrices in tissue engineering

Incorporation of heparin‐binding peptides into fibrin gels enhances neurite extension: an example of designer matrices in tissue engineering

Click synthesis of estradiol–cyclodextrin conjugates as cell compartment selective estrogens

Modified Cyclodextrins with Pendant Cationic and Anionic Moieties as Hosts for Highly Stable Inclusion Complexes and Molecular Recognition

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