Tailoring of integrin ligands: Probing the charge capability of the metal ion-dependent adhesion site

Journal of Medicinal Chemistry

Volumn 55, Issue 2, 2012, Pages 871-882

  Bollinger, Markus ^a   Manzenrieder, Florian ^a   Kolb, Roman ^a   Bochen, Alexander ^a   Neubauer, Stefanie ^a   Marinelli, Luciana ^b   Limongelli, Vittorio ^b   Novellino, Ettore ^b   Moessmer, Georg ^c   Pell, Reinhard ^d   Lindner, Wolfgang ^d   Fanous, Joseph ^e   Hoffman, Amnon ^e   Kessler, Horst ^a,f  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^d UNIVERSITY OF VIENNA   (Austria)

^e HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^f KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

[No Author keywords available]

Indexed keywords

1 (PHENYLSULFONAMIDO) 2 [4 [2 (PIPERIDIN 4 YL)ETHOXY]BENZAMID]ETHYLPHOSPHINIC ACID; 1 (PHENYLSULFONAMIDO) 2 [4 [2 (PIPERIDIN 4 YL)ETHOXY]BENZAMID]ETHYLPHOSPHONIC ACID; 1 (PHENYLSULFONAMIDO) 2 [4 [2 (PIPERIDIN 4 YL)ETHOXY]BENZAMID]ETHYLTHIOPHOSPHONIC ACID; INTEGRIN; INTEGRIN ALPHA 2B BETA 3; INTEGRIN RECEPTOR; METAL ION; METHYL 1 (PHENYLSULFONAMIDO) 2 [4 [2 (PIPERIDIN 4 YL)ETHOXY]BENZAMID]ETHYLPHOSPHONATE; PHOSPHINIC ACID DERIVATIVE; PROTEIN INHIBITOR; TIROFIBAN; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CELL ADHESION; CONTROLLED STUDY; DRUG PENETRATION; ELECTRICITY; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; MOLECULAR DOCKING; PROTEIN BINDING; PROTEIN INTERACTION; PROTON TRANSPORT; STATIC ELECTRICITY; SYNTHESIS; THROMBOCYTE AGGREGATION;

BINDING SITES; BLOOD PLATELETS; CACO-2 CELLS; CELL MEMBRANE PERMEABILITY; HUMANS; MODELS, MOLECULAR; ORGANOPHOSPHONATES; PHOSPHINIC ACIDS; PLATELET AGGREGATION INHIBITORS; PLATELET GLYCOPROTEIN GPIIB-IIIA COMPLEX; PROTEIN STRUCTURE, TERTIARY; QUANTUM THEORY; STATIC ELECTRICITY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84856383129     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2013826     Document Type: Article

References (52)

1. Meyer, A.; Auernheimer, J.; Modlinger, A.; Kessler, H. Targeting RGD recognizing integrins: Drug development, biomaterial research, tumor imaging and targeting Curr. Pharm. Des. 2006, 12, 2723-2747 (Pubitemid 44184633)
2. Mousa, S. A. Anti-integrin as novel drug-discovery targets: Potential therapeutic and diagnostic implications Curr. Opin. Chem. Biol. 2002, 6, 534-541 (Pubitemid 34804777)
3. Humphries, M. J. Integrin structure Biochem. Soc. Trans. 2000, 28, 311-339
4. Arnaout, M. A.; Mahalingam, B.; Xiong, J. P. Integrin structure, allostery, and bidirectional signaling Annu. Rev. Cell Dev. Biol. 2005, 21, 381-410 (Pubitemid 41740640)
5. Hynes, R. O. Integrins: Bidirectional, allosteric signaling machines Cell 2002, 110, 673-687 (Pubitemid 35283958)
6. Humphries, J. D.; Byron, A.; Humphries, M. J. Integrin ligands at a glance J. Cell Sci. 2006, 119, 3901-3903 (Pubitemid 44650863)
7. Ruoslahti, E. RGD and other recognition sequences for integrins Annu. Rev. Cell Dev. Biol. 1996, 12, 697-715 (Pubitemid 26422728)
8. Heckmann, D.; Laufer, B.; Marinelli, L.; Limongelli, V.; Novellino, E.; Zahn, G.; Stragies, R.; Kessler, H. Breaking the dogma of the metal-coordinating carboxylate group in integrin ligands: Introducing hydroxamic acids to the MIDAS to tune potency and selectivity Angew. Chem., Int. Ed. 2009, 48, 4436-4440
9. Cox, D.; Brennan, M.; Moran, N. Integrins as therapeutic targets: Lessons and opportunities Nat. Rev. Drug Discovery 2010, 9, 804-820
10. Mas-Moruno, C.; Rechenmacher, F.; Kessler, H. Cilengitide: The first anti-angiogenic small molecule drug candidate. Design, synthesis and clinical evaluation Anti-Cancer Agents Med. Chem. 2011, 10, 753-768
11. Shimaoka, M.; Springer, T. A. Therapeutic antagonists and conformational regulation of integrin function Nat. Rev. Drug Discovery 2003, 2, 703-716 (Pubitemid 37361786)
12. Hartman, G. D.; Egbertson, M. S.; Halczenko, W.; Laswell, W. L.; Duggan, M. E.; Smith, R. L.; Naylor, A. M.; Manno, P. D.; Lynch, R. J.; Zhang, G.; Chang, C. T.-C.; Gould, R. J. Non-peptide fibrinogen receptor antagonists. 1. Discovery and design of exosite inhibitors J. Med. Chem. 1992, 35, 4640-4642 (Pubitemid 23006685)
13. Topol, E. J.; Moliterno, D. J.; Herrmann, H. C.; Powers, E. R.; Grines, C. L.; Cohen, D. J.; Cohen, E. A.; Bertrand, M.; Neumann, F. J.; Stone, G. W.; DiBattiste, P. M.; Demopoulos, L. Comparison of two platelet glycoprotein IIb/IIIa inhibitors, tirofiban and abciximab, for the prevention of ischemic events with percutaneous coronary revascularization N. Engl. J. Med. 2001, 344, 1888-1894 (Pubitemid 32553357)
14. Cannon, C. P.; Weintraub, W. S.; Demopoulos, L. A.; Vicari, R.; Frey, M. J.; Lakkis, N.; Neumann, F. J.; Robertson, D. H.; DeLucca, P. T.; DiBattiste, P. M.; Gibson, C. M.; Braunwald, E. Comparison of early invasive and conservative strategies in patients with unstable coronary syndromes treated with the glycoprotein IIb/IIIa inhibitor tirofiban N. Engl. J. Med. 2001, 344, 1879-1887 (Pubitemid 32564900)
15. 3 antagonist J. Med. Chem. 2000, 43, 3736-3745
16. Frigerio, M.; Santagostino, M.; Sputore, S. A user-friendly entry to 2-iodoxybenzoic acid (IBX) J. Org. Chem. 1999, 64, 4537-4538
17. Frigerio, M.; Santagostino, M. A mild oxidizing reagent for alcohols and 1,2-diols: o-Iodoxybenzoic acid (IBX) in DMSO Tetrahedron Lett. 1994, 35, 8019-8022 (Pubitemid 24320215)
18. Liboska, R.; Pícha, J.; Hanclová, I.; Budesí nský, M.; Sanda, M.; Jirácek, J. Synthesis of methionine- and norleucine-derived phosphinopeptides Tetrahedron Lett. 2008, 49, 5629-5631
19. Zhukov, Y. N.; Khomutov, A. R.; Osipova, T. I.; Khomutov, R. M. Synthesis of phosphinic analogs of sulfur-containing amino acids Russ. Chem. Bull. 1999, 48, 1348-1351
20. Heckmann, D.; Meyer, A.; Laufer, B.; Zahn, G.; Stragies, R.; Kessler, H. Rational design of highly active and selective ligands for the α5β1 integrin receptor ChemBioChem 2008, 9, 1397-1407
21. 5 integrin dual inhibitors with improved bioavailability. Selection of the molecular core J. Med. Chem. 2005, 48, 926-934 (Pubitemid 40270439)
22. Hoffmann, C. V.; Pell, R.; Lämmerhofer, M.; Lindner, W. Synergistic effects on enantioselectivity of zwitterionic chiral stationary phases for separations of chiral acids, bases, and amino acids by HPLC Anal. Chem. 2008, 80, 8780-8789
23. Hoffmann, C. V.; Reischl, R.; Maier, N. M.; Lämmerhofer, M.; Lindner, W. Stationary phase-related investigations of quinine-based zwitterionic chiral stationary phases operated in anion-, cation-, and zwitterion-exchange modes J. Chromatogr., A 2009, 1216, 1147-1156
24. Maier, N. M.; Schefzick, S.; Lombardo, G. M.; Feliz, M.; Rissanen, K.; Lindner, W.; Lipkowitz, K. B. Elucidation of the chiral recognition mechanism of cinchona alkaloid carbamate-type receptors for 3,5-dinitrobenzoyl amino acids J. Am. Chem. Soc. 2002, 124, 8611-8629 (Pubitemid 34791030)
25. Lämmerhofer, M.; Hebenstreit, D.; Gavioli, E.; Lindner, W.; Mucha, A.; Kafarski, P.; Wieczorek, P. High-performance liquid chromatographic enantiomer separation and determination of absolute configurations of phosphinic acid analogues of dipeptides and their α-aminophosphinic acid precursors Tetrahedron: Asymmetry 2003, 14, 2557-2565 (Pubitemid 37093873)
26. Mas-Moruno, C.; Beck, J. G.; Doedens, L.; Frank, A. O.; Marinelli, L.; Cosconati, S.; Novellino, E.; Kessler, H. Increasing αvβ3 selectivity of the anti-angiogenic drug cilengitide by N -methylation Angew. Chem., Int. Ed. 2011, 50, 9496-9500
27. Chatterjee, J.; Ovadia, O.; Zahn, G.; Marinelli, L.; Hoffman, A.; Gilon, C.; Kessler, H. Multiple N-methylation by a designed approach enhances receptor selectivity J. Med. Chem. 2007, 50, 5878-5881
28. Tóth, O.; Calatzis, A.; Penz, S.; Losonczy, H.; Siess, W. Multiple electrode aggregometry: A new device to measure platelet aggregation in whole blood Thromb. Haemostasis 2006, 96, 781-788 (Pubitemid 44883819)
29. Halimeh, S.; Angelis, G.; Sander, A.; Edelbusch, C.; Rott, H.; Thedieck, S.; Mesters, R.; Schlegel, N.; Nowak-Gottl, U. Multiplate whole blood impedance point of care aggregometry: Preliminary reference values in healthy infants, children and adolescents Klin. Paediatr. 2010, 222, 158-163
30. Artursson, P.; Karlsson, J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells Biochem. Biophys. Res. Commun. 1991, 175, 880-885
31. Kelley, J. L.; McLean, E. W.; Crouch, R. C.; Averett, D. R.; Tuttle, J. V. [[(Guaninylalkyl)phosphinico]methyl]phosphonic acids. Multisubstrate analogue inhibitors of human erythrocyte purine nucleoside phosphorylase J. Med. Chem. 1995, 38, 1005-1014
32. Manzenrieder, F.; Frank, A. O.; Kessler, H. Phosphorus NMR spectroscopy as a versatile tool for compound library screening Angew. Chem., Int. Ed. 2008, 47, 2608-2611
33. Stirtan, W. G.; Withers, S. G. Phosphonate and α-fluorophosphonate analogue probes of the ionization state of pyridoxal 5′-phosphate (PLP) in glycogen phosphorylase Biochemistry (Moscow, Russ. Fed.) 1996, 35, 15057-15064
34. Selvam, C.; Goudet, C.; Oueslati, N.; Pin, J. P.; Acher, F. C. l -(+)-2-Amino-4-thiophosphonobutyric acid (l -thioAP4), a new potent agonist of group III metabotropic glutamate receptors: Increased distal acidity affords enhanced potency J. Med. Chem. 2007, 50, 4656-4664 (Pubitemid 47469678)
35. 13C NMR of glyphosate: Comparison of pH titrations to the herbicidal dead-end complex with 5- enolpyruvoylshikimate-3-phosphate synthase Biochemistry (Moscow, Russ. Fed.) 1989, 28, 3856-3868 (Pubitemid 19125434)
36. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem. 1998, 19, 1639-1662 (Pubitemid 128590223)
37. Huey, R.; Morris, G. M.; Olson, A. J.; Goodsell, D. S. A semiempirical free energy force field with charge-based desolvation J. Comput. Chem. 2007, 28, 1145-1152 (Pubitemid 46506716)
38. Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 1997, 267, 727-748 (Pubitemid 27170693)
39. Rarey, M.; Kramer, B.; Lengauer, T.; Klebe, G. A fast flexible docking method using an incremental construction algorithm J. Mol. Biol. 1996, 261, 470-489 (Pubitemid 26335901)
40. Gohlke, H.; Hendlich, M.; Klebe, G. Knowledge-based scoring function to predict protein-ligand interactions J. Mol. Biol. 2000, 295, 337-356 (Pubitemid 30045364)
41. Oelschlaeger, P.; Klahn, M.; Beard, W. A.; Wilson, S. H.; Warshel, A. Magnesium-cationic dummy atom molecules enhance representation of DNA polymerase β in molecular dynamics simulations: Improved accuracy in studies of structural features and mutational effects J. Mol. Biol. 2007, 366, 687-701 (Pubitemid 46138101)
42. Rucker, R.; Oelschlaeger, P.; Warshel, A. A binding free energy decomposition approach for accurate calculations of the fidelity of DNA polymerases Proteins 2010, 78, 671-680
43. Xiang, Y.; Oelschlaeger, P.; Florian, J.; Goodman, M. F.; Warshel, A. Simulating the effect of DNA polymerase mutations on transition-state energetics and fidelity: Evaluating amino acid group contribution and allosteric coupling for ionized residues in human Pol β Biochemistry (Moscow, Russ. Fed.) 2006, 45, 7036-7048 (Pubitemid 43877392)
44. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. NMR chemical shifts of common laboratory solvents as trace impurities J. Org. Chem. 1997, 62, 7512-7515
45. Porcheddu, A.; Giacomelli, G.; Piredda, I.; Carta, M.; Nieddu, G. A practical and efficient approach to PNA monomers compatible with Fmoc-mediated solid-phase synthesis protocols Eur. J. Org. Chem. 2008, 2008, 5786-5797
46. Dixon, S. L.; Jurs, P. C. Estimation of pKa for organic oxyacids using calculated atomic charges J. Comput. Chem. 1993, 14, 1460-1467
47. Csizmadia, F.; Tsantili-Kakoulidou, A.; Panderi, I.; Darvas, F. Prediction of distribution coefficient from structure. 1. Estimation method J. Pharm. Sci. 1997, 86, 865-871 (Pubitemid 27297501)
48. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. A second generation force field for the simulation of proteins, nucleic acids, and organic molecules J. Am. Chem. Soc. 1995, 117, 5179-5197
49. Wang, J.; Cieplak, P.; Kollman, P. A. How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules? J. Comput. Chem. 2000, 21, 1049-1074
50. Baker, N. A.; Sept, D.; Joseph, S.; Holst, M. J.; McCammon, J. A. Electrostatics of nanosystems: Application to microtubules and the ribosome Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 10037-10041 (Pubitemid 32802969)
51. Schüttelkopf, A. W.; van Aalten, D. M. F. PRODRG: A tool for high-throughput crystallography of protein-ligand complexes Acta Crystallogr. 2004, D60, 1355-1363 (Pubitemid 41079731)
52. Gasteiger, J.; Marsili, M. Iterative partial equalization of orbital electronegativity: A rapid access to atomic charges Tetrahedron 1980, 36, 3219-3228