Toward multivalent signaling across G protein-coupled receptors from poly(amidoamine) dendrimers

Bioconjugate Chemistry

Volumn 19, Issue 2, 2008, Pages 406-411

  Kim, Yoonkyung ^a   Hechler, Béatrice ^b   Klutz, Athena M ^a   Gachet, Christian ^b   Jacobson, Kenneth A ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b INSERM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PLATELETS; PROTEINS;

ANTI-INFLAMMATORIES; EXTRACELLULAR; G PROTEIN COUPLED RECEPTORS; PAMAM DENDRIMER; PHARMACOLOGICAL PROFILES; POLYAMIDOAMINE DENDRIMERS; RECEPTOR LIGANDS;

DENDRIMERS;

2 [4 (2 CARBOXYETHYL)PHENETHYLAMINO]ADENOSINE 5' (N ETHYLCARBOXAMIDE); DENDRIMER; G PROTEIN COUPLED RECEPTOR; POLYAMIDOAMINE;

ARTICLE; CONTROLLED STUDY; FLUORESCENCE; HUMAN; HUMAN CELL; IN VITRO STUDY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; SPECTROSCOPY; THROMBOCYTE;

EID: 39749132227     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc700327u     Document Type: Article

References (53)

1. Landry, Y., Niederhoffer, N., Sick, E., and Gies, J. P. (2006) Heptahelical and other G-protein-coupled receptors (GPCRs) signaling. Curr. Med. Chem. 13, 51-63.
2. Ratnala, V. R., Kiihne, S. R., Buda, F., Leurs, R., de Groot, H. J., and DeGrip, W. J. (2007) Solid-state NMR evidence for a protonation switch in the binding pocket of the H1 receptor upon binding of the agonist histamine. J. Am. Chem. Soc. 129, 867-872.
3. Jacobson, K. A., and Daly, J. W. (1991) Purine functionalized congeners as molecular probes for adenosine receptors. Nucleosides Nucleotides 10, 1029-1038.
4. 1-adenosine receptors. J. Med. Chem. 28, 1341-1346.
5. Tomalia, D. A. (2005) Birth of a new macromolecular architecture: dendrimers as quantized building blocks for nanoscale synthetic polymer chemistry. Prog. Polym. Sci. 30, 294-324.
6. Grayson, S. M., and Fréchet, J. M. J. (2001) Convergent dendrons and dendrimers: from synthesis to applications. Chem. Rev. 101, 3819-3867.
7. Zeng, F., and Zimmerman, S. C. (1997) Dendrimers in supramolecular chemistry: from molecular recognition to self-assembly. Chem. Rev. 97, 1681-1712.
8. Lee, C. C., MacKay, J. A., Fréchet, J. M. J., and Szoka, F. C. (2005) Designing dendrimers for biological applications. Nat. Biotechnol. 23, 1517-1526.
9. Svenson, S., and Tomalia, D. A. (2005) Dendrimers in biomedical applications-reflections on the field. Adv. Drug Delivery Rev. 57, 2106-2129.
10. Shabat, D., Amir, R. J., Gopin, A., Pessah, N., and Shamis, M. (2004) Chemical adaptor systems. Chem. Eur. J. 10, 2626-2634.
11. Boas, U., and Heegaard, P. M. H. (2004) Dendrimers in drug research. Chem. Soc. Rev. 33, 43-63.
12. Stiriba, S.-E., Frey, H., and Haag, R. (2002) Dendritic polymers in biomedical applications: from potential to clinical use in diagnostics and therapy. Angew. Chem., Int. Ed. 41, 1329-1334.
13. Zhou, J., Wu, J., Hafdi, N., Behr, J.-P., Erbacher, P., and Peng, L. (2006) PAMAM dendrimers for efficient siRNA delivery and potent gene silencing. Chem. Commun. 2362-2364.
14. Luo, D., Haverstick, K., Belcheva, N., Han, E., and Saltzman, W. M. (2002) Poly(ethylene glycol)-conjugated PAMAM dendrimer for biocompatible, high-efficiency DNA delivery. Macromolecules 35, 3456-3462.
15. Tang, M. X., Redemann, C. T., and Szoka, F. C., Jr. (1996) In vitro gene delivery by degraded polyamidoamine dendrimers. Bioconjugate Chem. 7, 703-714.
16. Haensler, J., and Szoka, F. C., Jr. (1993) Polyamidoamine cascade polymers mediate efficient transfection of cells in culture. Bioconjugate Chem. 4, 372-379.
17. Gillies, E. R., and Fréchet, J. M. J. (2005) Dendrimers and dendritic polymers in drug delivery. Drug Discovery Today 10, 35-43.
18. D'Emanuele, A., and Attwood, D. (2005) Dendrimer-drug interactions. Adv. Drug Delivery Rev. 57, 2147-2162.
19. Haag, R. (2004) Supramolecular drug delivery systems based on polymeric core-shell architectures. Angew. Chem., Int. Ed. 43, 278-282.
20. Patri, A. K., Majoras, I. J., and Baker, J. R., Jr. (2002) Dendritic polymer macromolecular carriers for drug delivery. Curr. Opin. Chem. Biol. 6, 466-471.
21. Liu, M., and Fréchet, J. M. J. (1999) Designing dendrimers for drug delivery. Pharm. Sci. Tech. Today 2, 393-401.
22. Woller, E. K., Walter, E. D., Morgan, J. R., Singel, D. J., and Cloninger, M. J. (2003) Altering the strength of lectin binding interactions and controlling the amount of lectin clustering using mannose/hydroxyl- functionalized dendrimers. J. Am. Chem. Soc. 125, 8820-8826.
23. Woller, E. K., and Cloninger, M. J. (2002) The lectin-binding properties of six generations of mannose-functionalized dendrimers. Org. Lett. 4, 7-10.
24. Jayaraman, N., Nepogodiev, S. A., and Stoddart, J. F. (1997) Synthetic carbohydrate-containing dendrimers. Chem. Eur. J. 3, 1193-1199.
25. Page, D., and Roy, R. (1997) Synthesis and biological properties of mannosylated starburst poly(amidoamine) dendrimers. Bioconjugate Chem. 8, 714-723.
26. Kieburg, C., and Lindhorst, T. K. (1997) Glycodendrimer synthesis without using protecting groups. Tetrahedron Lett. 38, 3885-3888.
27. Mammen, M., Choi, S.-K., and Whitesides, G. M. (1998) Polyvalent interactions in biological systems: implications for design and use of multivalent ligands and inhibitors. Angew. Chem., Int. Ed. 37, 2754-2794.
28. Krause, W., Hackmann-Schlichter, N., Maier, F. K., and Müller, R. (2000) Dendrimers in diagnostics. Top. Curr. Chem. 210, 261-308.
29. Wathier, M., Jung, P. J., Carnahan, M. A., Kim, T., and Grinstaff, M. W. (2004) Dendritic macromers as in situ polymerizing biomaterials for securing cataract incisions. J. Am. Chem. Soc. 126, 12744-12745.
30. Grinstaff, M. W. (2002) Biodendrimers: new polymeric biomaterials for tissue engineering. Chem. Eur. J. 8, 2838-2846.
31. Carnahan, M. A., Middleton, C., Kim, J., Kim, T., and Grinstaff, M. W. (2002) Hybrid dendritic-linear polyester-ethers for in situ photopolymerization. J. Am. Chem. Soc. 124, 5291-5293.
32. Lee, H., Baker, J. R., Jr., and Larson, R. G. (2006) Molecular dynamics studies of the size, shape, and internal structure of 0% and 90% acetylated fifth-generation polyamidoamine dendrimers in water and methanol. J. Phys. Chem. B 110, 4014-4019.
33. Maiti, P. K., Çaǧin, T., Wang, G., and Goddard, W. A. (2004) Structure of PAMAM dendrimers: generations 1 through 11. Macromolecules 37, 6236-6254.
34. Lee, I., Athey, B. D., Wetzel, A. W., Meixner, W., and Baker, J. R., Jr. (2002) Structural molecular dynamics studies on polyamidoamine dendrimers for a therapeutic application: effects of pH and generation. Macromolecules 35, 4510-4520.
35. Esfand, R., and Tomalia, D. A. (2001) Poly(amidoamine) (PAMAM) dendrimers: from biomimicry to drug delivery and biomedical applications. Drug Discovery Today 6, 427-436.
36. Shi, X., Majoras, I. J., Patri, A. K., Bi, X., Islam, M. T., Desai, A., Ganser, T. R., and Baker, J. R., Jr. (2006) Molecular heterogeneity analysis of poly(amidoamine) dendrimer-based mono- and multifunctional nanodevices by capillary electrophoresis. Analyst 131, 374-381.
37. Jacobson, K. A., and Gao, Z.-G. (2006) Adenosine receptors as therapeutic targets. Nat. Rev. Drug Discovery 5, 247-264.
38. Yan, L., Burbiel, J. C., Maass, A., and Müller, C. E. (2003) Adenosine receptor agonists: from basic medicinal chemistry to clinical development. Exp. Opin. Emerging Drugs 8, 537-576.
39. Fredholm, B. B., IJzerman, A. P., Jacobson, K. A., Klotz, K.-N., and Linden, J. (2001) International Union of Pharmacology. XXV. Nomenclature and classification of adenosine receptors. Pharmacol. Rev. 53, 527-552.
40. 2 receptor ligands. J. Med. Chem. 33, 1919-1924.
41. 2 receptors in rat brain. J. Pharm. Exp. Therap. 251, 888-893.
42. 2 selective adenosine receptor agonist with preferential hypotensive activity. J. Pharm. Exp. Therap. 251, 47-55.
43. Haugland, R. P. (2002) Handbook of Fluorescent Probes and Research Products, 9th ed., Molecular Probes, Invitrogen, pp 20-35.
44. Panchuk-Voloshina, N., Haugland, R. P., Bishop-Stewart, J., Bhalgat, M. K., Millard, P. J., Mao, F., Leung, W.-Y., and Haugland, R. P. (1999) Alexa dyes, a series of new fluorescent dyes that yield exceptionally bright, photostable conjugates. J. Histochem. Cytochem. 47, 1179-1188.
45. Peterson, J., Allikmaa, V., Subbi, J., Pehk, T., and Lopp, M. (2003) Structural deviations in poly(amidoamine) dendrimers: a MALDI-TOF MS analysis. Eur. Polym. J. 39, 33-42.
46. Petkova, V., Parvanova, V., Tomaliab, D., Swansonb, D., Bergstromb, D., and Vogt, T. (2005) 3D structure of dendritic and hyper-branched macromolecules by X-ray diffraction. Solid State Commun. 134, 671-675.
47. Gachet, C. (2006) Regulation of platelet functions by P2 receptors. Annu. Rev. Pharmacol. Toxicol. 46, 277-300.
48. 2A adenosine receptors in human peripheral blood cells. Br. J. Pharmacol. 129, 2-11.
49. Ledent, C., Vaugeois, J.-M., Schiffmann, S. N., Pedrazzini, T., Yacoubi, M. E., Vanderhaeghen, J.-J., Costentin, J., Heath, J. K., Vassart, G., and Parmentier, M. (1997) Aggressiveness, hypoalgesia and high blood pressure in mice lacking the adenosine A2a receptor. Nature 388, 674-678.
50. Gurden, M. F., Coates, J., Ellis, F., Evans, B., Foster, M., Hornby, E., Kennedy, I., Martin, D. P., Strong, P., and Vardey, C. J. (1993) Functional characterization of three adenosine receptor types. Br. J. Pharmacol. 109, 693-698.
51. 3 adenosine receptor agonists. J. Biol. Chem. 275, 30272-30279.
52. Jacobson, K. A., Lipkowski, A. W., Moody, T. W., Padgett, W., Pijl, E., Kirk, K. L., and Daly, J. W. (1987) Binary drugs: conjugates of purines and a peptide that bind to both adenosine and substance P receptors. J. Med. Chem. 30, 1529-1532.
53. Handagama, P. J., Shuman, M. A., and Bainton, D. F. (1989) Incorporation of intravenously injected albumin, immunoglobulin G, and fibrinogen in guinea pig megakaryocyte granules. J. Clin. Invest. 84, 73-82.