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Literature DB >> 18925770

Peptide-mediated cellular uptake of cryptophane.

Garry K Seward¹, Qian Wei, Ivan J Dmochowski.

Abstract

Cryptophane-A has generated considerable interest based on its high affinity for xenon and potential for creating biosensors for (129)Xe nuclear magnetic resonance (NMR) spectroscopy. Here, we report the cellular delivery of three peptide-functionalized cryptophane biosensors. Cryptophanes were delivered using two cationic cell penetrating peptides into several human cancer and normal cell lines. An RGD peptide targeting alpha(v)beta(3) integrin receptor was shown to increase specificity of cryptophane cell uptake. Labeling the peptides with Cy3 made it possible to monitor cellular delivery using confocal laser scanning microscopy. The peptido-cryptophanes were determined to be relatively nontoxic by MTT assay at the micromolar cryptophane concentrations that are required for (129)Xe NMR biosensing experiments.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：

Year: 2008 PMID： 18925770 PMCID： PMC2645951 DOI： 10.1021/bc8002265

Source DB: PubMed Journal: Bioconjug Chem ISSN： 1043-1802 Impact factor: 4.774

48 in total

1. Functionalized xenon as a biosensor.

Authors: M M Spence; S M Rubin; I E Dimitrov; E J Ruiz; D E Wemmer; A Pines; S Q Yao; F Tian; P G Schultz
Journal: Proc Natl Acad Sci U S A Date: 2001-09-04 Impact factor: 11.205

Review 2. Guanidinium rich peptide transporters and drug delivery.

Authors: Lee R Wright; Jonathan B Rothbard; Paul A Wender
Journal: Curr Protein Pept Sci Date: 2003-04 Impact factor: 3.272

3. Fullerene-based amino acid nanoparticle interactions with human epidermal keratinocytes.

Authors: Jillian G Rouse; Jianzhong Yang; Andrew R Barron; Nancy A Monteiro-Riviere
Journal: Toxicol In Vitro Date: 2006-05-03 Impact factor: 3.500

Review 4. Cell-penetrating peptides: mechanism and kinetics of cargo delivery.

Authors: Matjaz Zorko; Ulo Langel
Journal: Adv Drug Deliv Rev Date: 2005-01-22 Impact factor: 15.470

5. Optimization of xenon biosensors for detection of protein interactions.

Authors: Thomas J Lowery; Sandra Garcia; Lana Chavez; E Janette Ruiz; Tom Wu; Thierry Brotin; Jean-Pierre Dutasta; David S King; Peter G Schultz; Alex Pines; David E Wemmer
Journal: Chembiochem Date: 2006-01 Impact factor: 3.164

6. The use of fullerene substituted phenylalanine amino acid as a passport for peptides through cell membranes.

Authors: Jianzhong Yang; Kuan Wang; Jonathan Driver; Jianhua Yang; Andrew R Barron
Journal: Org Biomol Chem Date: 2006-11-17 Impact factor: 3.876

7. Peptide-mediated cell transport of water soluble porphyrin conjugates.

Authors: Martha Sibrian-Vazquez; Timothy J Jensen; Robert P Hammer; M Graça H Vicente
Journal: J Med Chem Date: 2006-02-23 Impact factor: 7.446

8. Activation of integrin alpha(V)beta(3) regulates cell adhesion and migration to bone sialoprotein.

Authors: T V Byzova; W Kim; R J Midura; E F Plow
Journal: Exp Cell Res Date: 2000-02-01 Impact factor: 3.905

9. Reassessment of Ellman's reagent.

Authors: P W Riddles; R L Blakeley; B Zerner
Journal: Methods Enzymol Date: 1983 Impact factor: 1.600

10. Design, synthesis, and evaluation of radiolabeled integrin alpha v beta 3 receptor antagonists for tumor imaging and radiotherapy.

Authors: Thomas D Harris; Shirley Kalogeropoulos; Tiffany Nguyen; Shuang Liu; Judit Bartis; Charles Ellars; Scott Edwards; David Onthank; Paula Silva; Padmaja Yalamanchili; Simon Robinson; Joel Lazewatsky; John Barrett; Jeffrey Bozarth
Journal: Cancer Biother Radiopharm Date: 2003-08 Impact factor: 3.099

23 in total

1. Cell-compatible, integrin-targeted cryptophane-¹²⁹Xe NMR biosensors.

Authors: Garry K Seward; Yubin Bai; Najat S Khan; Ivan J Dmochowski
Journal: Chem Sci Date: 2011-06 Impact factor: 9.825

2. Multiple hindered rotators in a gyroscope-inspired tribenzylamine hemicryptophane.

Authors: Najat S Khan; Jose Manuel Perez-Aguilar; Tara Kaufmann; P Aru Hill; Olena Taratula; One-Sun Lee; Patrick J Carroll; Jeffery G Saven; Ivan J Dmochowski
Journal: J Org Chem Date: 2011-01-27 Impact factor: 4.354

3. Anti-EpCAM scFv gadolinium chelate: a novel targeted MRI contrast agent for imaging of colorectal cancer.

Authors: Kannika Khantasup; Pairash Saiviroonporn; Suwatchai Jarussophon; Warangkana Chantima; Tararaj Dharakul
Journal: MAGMA Date: 2018-05-08 Impact factor: 2.310

4. Toward the Ideal Synthesis and Transformative Therapies: The Roles of Step Economy and Function Oriented Synthesis.

Authors: Paul A Wender
Journal: Tetrahedron Date: 2013-06-07 Impact factor: 2.457

5. A "Smart" ¹²⁸Xe NMR Biosensor for pH-Dependent Cell Labeling.

Authors: Brittany A Riggle; Yanfei Wang; Ivan J Dmochowski
Journal: J Am Chem Soc Date: 2015-04-20 Impact factor: 15.419

6. Development of an antibody-based, modular biosensor for 129Xe NMR molecular imaging of cells at nanomolar concentrations.

Authors: Honor M Rose; Christopher Witte; Federica Rossella; Stefan Klippel; Christian Freund; Leif Schröder
Journal: Proc Natl Acad Sci U S A Date: 2014-07-28 Impact factor: 11.205

Peptide-mediated cellular uptake of cryptophane.

1. Functionalized xenon as a biosensor.

Review 2. Guanidinium rich peptide transporters and drug delivery.

3. Fullerene-based amino acid nanoparticle interactions with human epidermal keratinocytes.

Review 4. Cell-penetrating peptides: mechanism and kinetics of cargo delivery.

5. Optimization of xenon biosensors for detection of protein interactions.

6. The use of fullerene substituted phenylalanine amino acid as a passport for peptides through cell membranes.

7. Peptide-mediated cell transport of water soluble porphyrin conjugates.

8. Activation of integrin alpha(V)beta(3) regulates cell adhesion and migration to bone sialoprotein.

9. Reassessment of Ellman's reagent.

10. Design, synthesis, and evaluation of radiolabeled integrin alpha v beta 3 receptor antagonists for tumor imaging and radiotherapy.

1. Cell-compatible, integrin-targeted cryptophane-¹²⁹Xe NMR biosensors.

2. Multiple hindered rotators in a gyroscope-inspired tribenzylamine hemicryptophane.

3. Anti-EpCAM scFv gadolinium chelate: a novel targeted MRI contrast agent for imaging of colorectal cancer.

4. Toward the Ideal Synthesis and Transformative Therapies: The Roles of Step Economy and Function Oriented Synthesis.

5. A "Smart" ¹²⁸Xe NMR Biosensor for pH-Dependent Cell Labeling.

6. Development of an antibody-based, modular biosensor for 129Xe NMR molecular imaging of cells at nanomolar concentrations.

7. Measurement of radon and xenon binding to a cryptophane molecular host.

8. Cryptophane xenon-129 nuclear magnetic resonance biosensors targeting human carbonic anhydrase.

9. Utilizing a water-soluble cryptophane with fast xenon exchange rates for picomolar sensitivity NMR measurements.

Review 10. Molecular Sensing with Host Systems for Hyperpolarized ¹²⁹Xe.

Review 2. Guanidinium rich peptide transporters and drug delivery.

Review 4. Cell-penetrating peptides: mechanism and kinetics of cargo delivery.

Review 10. Molecular Sensing with Host Systems for Hyperpolarized 129Xe.

Review 10. Molecular Sensing with Host Systems for Hyperpolarized ¹²⁹Xe.