Comparative analysis of photocaged RGDS peptides for cell patterning

Journal of Biomedical Materials Research - Part A

Volumn 101 A, Issue 3, 2013, Pages 787-796

  Goubko, Catherine A ^a   Basak, Ajoy ^b   Majumdar, Swapan ^b   Jarrell, Harold ^c   Khieu, Nam Huan ^c   Cao, Xudong ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

^b OTTAWA HOSPITAL RESEARCH INSTITUTE   (Canada)

^c NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

2 nitrobenzyl photocage; Cell patterning; Docking; Photochemistry; RGDS peptide

Indexed keywords

2-NITROBENZYL; BIOLOGICAL APPLICATIONS; CELL-PATTERNING; COMPARATIVE ANALYSIS; MODELING PREDICTIONS; PHYSIOLOGICAL PROPERTIES; RGDS PEPTIDES; SOLID PHASE SYNTHESIS;

BIOLOGICAL MATERIALS; CELL ADHESION; CELL MEMBRANES; DOCKING; PHOTOCHEMICAL REACTIONS; RATE CONSTANTS;

PEPTIDES;

ALPHA V BETA 3 INTEGRIN RECEPTOR; ARGINYLGLYCYLASPARTYLSERINE; BENZYL DERIVATIVE; INTEGRIN RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CELL ADHESION; CELL PATTERNING; CELLULAR PARAMETERS; CONTROLLED STUDY; ENZYME LINKED IMMUNOSORBENT ASSAY; HYDROGEL; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOLECULAR MODEL; MOLECULAR STABILITY; PHOTOLYSIS; PHOTOSENSITIVITY; PHYSIOLOGY; PROTEIN BINDING; PROTEIN FUNCTION; PROTEIN SYNTHESIS; SOLID;

ANIMALS; CELL ADHESION; COATED MATERIALS, BIOCOMPATIBLE; HUMANS; INTEGRIN ALPHAVBETA3; MOLECULAR DOCKING SIMULATION; OLIGOPEPTIDES; PHOTOCHEMICAL PROCESSES; PROTEIN BINDING;

EID: 84876172813     PISSN: 15493296     EISSN: 15524965     Source Type: Journal    
DOI: 10.1002/jbm.a.34381     Document Type: Article

References (32)

1. Yu H, Li J, Wu D, Qiu Z, Zhang Y. Chemistry and biological applications of photo-labile organic molecules. Chem Soc Rev 2010;39: 464-473.
2. Young DD, Deiters A. Photochemical control of biological processes. Org Biomol Chem 2007;5:999-1005.
3. Shigeri Y, Tatsu Y, Yumoto N. Synthesis and application of caged peptides and proteins. Pharmacol Ther 2001;91:85-92.
4. Ellis-Davies GCR. Caged compounds: Photorelease technology for control of cellular chemistry and physiology. Nat Methods 2007;4: 619-628.
5. Bourgault S, Letourneau M, Fournier A. Development of photolabile caged analogs of endothelin-1. Peptides 2007;28:1074-1082.
6. Tatsu Y, Nishigaki T, Darszon A, Yumoto N. A caged sperm-activating peptide that has a photocleavable protecting group on the backbone amide. FEBS Lett 2002;525:20-24.
7. Hersel U, Dahmen C, Kessler H. RGD modified polymers: Biomaterials for stimulated cell adhesion and beyond. Biomaterials 2003;24:4385-4415.
8. Ohmuro-Matsuyama Y, Tatsu Y. Photocontrolled cell adhesion on a surface functionalized with a caged arginine-glycine-aspartate peptide13. Angew Chem Int Ed 2008;47:7527-7529.
9. Petersen S, Alonso JM, Specht A, Duodu P, Goeldner M, de Campo A. Phototriggering of cell adhesion by caged cyclic RGD peptides. Angew Chem Int Ed 2008;47:3192-3195.
10. Wirkner M, Alonso JM, Maus V, Salierno M, Lee TT, García AJ, del Campo A. Triggered cell release from materials using bioadhesive photocleavable linkers. Adv Mater 2011;23:3907-3910.
11. Goubko C, Majumdar S, Basak A, Cao X. Hydrogel cell patterning incorporating photocaged RGDS peptides. Biomed Microdevices 2010;12:555-568.
12. Luo Y, Shoichet MS. A photolabile hydrogel for guided three-dimensional cell growth and migration. Nat Mater 2004;3:249-253.
13. Moon JJ, Hahn MS, Kim I, Nsiah BA, West JL. Micropatterning of poly(ethylene glycol) diacrylate hydrogels with biomolecules to regulate and guide endothelial morphogenesis. Tissue Eng Part A 2009;15:579.
14. Myers AG, Gleason JL, Yoon T, Kung DW. Highly practical methodology for the synthesis of D- and l-α-amino acids, N-protected a-amino acids, and N-methyl-α-amino acids. J Am Chem Soc 1997;119:656-673.
15. Basak A, Mitra A, Basak S, Pasko C, Chretien M, Seaton P. A fluorogenic peptide containing the processing site of human SARS corona virus S-protein: Kinetic evaluation and NMR structure elucidation. ChemBioChem 2007;8:1029-1037.
16. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 1998;19:1639-1662.
17. Huey R, Morris GM, Olson AJ, Goodsell DS. A semiempirical free energy force field with charge-based desolvation. J Comput Chem 2007;28:1145-1152.
18. Marinelli L, Lavecchia A, Gottschalk KE, Novellino E, Kessler H. Docking studies on aVb3 integrin ligands: Pharmacophore refinement and implications for drug design. J Med Chem 2003;46: 4393-4404.
19. Xiong J-P, Stehle T, Zhang R, Joachimiak A, Frech M, Simon LG, Arnaout MA. Crystal structure of the extracellular segment of integrin aVb3 in complex with an Arg-Gly-Asp ligand. Science 2002;296:151-155.
20. Cheng F, Oldfield E. Inhibition of isoprene biosynthesis pathway enzymes by phosphonates, bisphosphonates, and diphosphates. J Med Chem 2004;47:5149-5158.
21. Johnson E, Kent S. Synthesis, stability and optimized photolytic cleavage of 4-methoxy-2-nitrobenzyl backbone-protected peptides. Chem Commun 2006:1557-1559.
22. Nandy SK, Agnes RS, Lawrence DS. Photochemically-activated probes of protein-protein interactions. Org Lett 2007;9:2249-2252.
23. Zhang Z, Hatta H, Ito T, Nishimoto S-I. Synthesis and photochemical properties of photoactivated antitumor prodrugs releasing 5-fluorouracil. Org Biomol Chem 2005;3:592-596.
24. Furuta T, Noguchi K. Controlling cellular systems with Bhc-caged compounds. Trends Anal Chem 2004;23:511-519.
25. Kim MS, Diamond SL. Photocleavage of o-nitrobenzyl ether derivatives for rapid biomedical release applications. Bioorg Med Chem Lett 2006;16:4007-4010.
26. Bogdanowich-Knipp SJ, Chakrabarti S, Williams TD, Dillman RK, Siahaan TJ. Solution stability of linear vs. cyclic RGD peptides. J Pept Res 1999;53:530-541.
27. Goeldner M, Givens R. Dynamic Studies in Biology: Phototriggers, Photoswitches and Caged Biomolecules. Weinheim: Wiley-VCH; 2005. 557 p.
28. Goolcharran G, Borchardt RT. Kinetics of diketopiperazine formation using model peptides. J Pharm Sci 1997;87:283-288.
29. Benedetto S, Pulito R, Crich SG, Tarone G, Aime S, Silengo L, Hamm J. Quantification of the expression level of integrin receptor aVb3 in cell lines and MR imaging with antibody-coated iron oxide particles. Magn Reson Med 2006;56:711-716.
30. Dechantsreiter MA, Planker E, Matha B, Lohof E, Holzemann G, Jonczyk A, Goodman SL, Kessler H. N-Methylated cyclic RGD peptides as highly active and selective alpha(V)beta(3) integrin antagonists. J Med Chem 1999;42:3033-3040.
31. Bowditch RD, Halloran CE, Aota S, Obara M, Plow EF, Yamada KM, Ginsberg MH. Integrin aIIbb3 (platelet GPIIb-IIIa) recognizes multiple sites in fibronectin. J Biol Chem 1991;266:23323-23328.
32. Bowditch RD, Hariharan M, Tominna EF, Smith JW, Yamada KM, Getzoff ED, Ginsberg MH. Identification of a novel integrin binding site in fibronectin. J Biol Chem 1994;269:10856-10863.