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Pure Appl. Chem., 1989, Vol. 61, No. 5, pp. 923-932

http://dx.doi.org/10.1351/pac198961050923

Hydrophobic interactions in biological systems: some background information based on ligand-ligand interactions in metal ion complexes

H. Sigel

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  • EL-Gahami Mohamed A., Al-Bogami Abdullah S., Albishri Hassan M.: Medium effect on the dimethyltin(IV) complexes of 2-(N-morpholino) ethanesulfonic and 3-(N-morpholino) propanesulfonic acid. Journal of Molecular Liquids 2014, 193, 45. <http://dx.doi.org/10.1016/j.molliq.2013.12.016>
  • Jalilov Almaz S., Patwardhan Sameer, Singh Arunoday, Simeon Tomekia, Sarjeant Amy A., Schatz George C., Lewis Frederick D.: Structure and Electronic Spectra of Purine–Methyl Viologen Charge Transfer Complexes. J. Phys. Chem. B 2014, 118, 125. <http://dx.doi.org/10.1021/jp410348b>
  • Blindauer Claudia A., Sigel Astrid, Operschall Bert P., Holý Antonin, Sigel Helmut: Extent of Intramolecular π Stacks in Aqueous Solution in Mixed-Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and 1-[2-(Phosphonomethoxy)ethyl]cytosine (PMEC), a Relative of Antivirally Active Acyclic Nucleotide Analogues (Part 72) [1, 2]. Z. anorg. allg. Chem. 2013, 639, 1661. <http://dx.doi.org/10.1002/zaac.201300095>
  • Aljahdali M., Foti Claudia, El-Sherif Ahmed A., Mohamed Mahmoud M. A., Soliman Ahmed A., Al Ruqi Obaid S.: Potentiometric determination of stability constants and thermodynamic data for dimethyltin(IV) dichloride complexes with iminobis(methylphosphonic acid) in water and dioxane–water mixtures. Monatsh Chem 2013, 144, 1467. <http://dx.doi.org/10.1007/s00706-013-1023-6>
  • El-Gahami M. A., Albishri H. M.: Equilibrium Studies of Dibutyltin(IV)–Zwitterionic Buffer Complexation. J Solution Chem 2013, 42, 2012. <http://dx.doi.org/10.1007/s10953-013-0088-5>
  • El-Sherif Ahmed A.: Kinetics and Mechanism for Hydrolysis of α-Amino Acid Esters in Mixed Ligand Complexes with Zn(II)–Nitrilo-tris(methyl phosphonic Acid). J Solution Chem 2012, 41, 249. <http://dx.doi.org/10.1007/s10953-012-9799-2>
  • El-Sherif Ahmed A.: Potentiometric Determination of the Stability Constants of Trimethyltin(IV) Chloride Complexes with Imino-bis(Methylphosphonic Acid) in Water and Dioxane–Water Mixtures. J Solution Chem 2012, 41, 392. <http://dx.doi.org/10.1007/s10953-012-9806-7>
  • Padmaja Nimmagadda, Rao Gollapalli Nageswara: Speciation Studies of Pb(II), Cd(II) and Hg(II) Complexes of 1,10-Phenanthroline in 1,4 Dioxan–Water Mixtures. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 2012, 82, 151. <http://dx.doi.org/10.1007/s40010-012-0024-x>
  • Shoukry Mohamed M., Hassouna M.M., Mahmoud R.K.: Palladium(II) complex taken as a model of an antitumour agent: Synthesis and equilibrium investigation involving biologically relevant ligands. Comptes Rendus Chimie 2012, 15, 356. <http://dx.doi.org/10.1016/j.crci.2011.12.003>
  • Hassan Safaa S., Shoukry Mohamed M., van Eldik Rudi: Thermodynamics of the interaction of ruthenium(iii) polyaminecarboxylate complexes with bio-relevant ligands. Deactivation of the complexes as NO scavengers by thiol ligands. Dalton Trans. 2012, 41, 13447. <http://dx.doi.org/10.1039/c2dt31730c>
  • Knobloch Bernd, Mucha Ariel, Operschall Bert P., Sigel Helmut, Jeżowska-Bojczuk Małgorzata, Kozłowski Henryk, Sigel Roland K. O.: Stability and Structure of Mixed-Ligand Metal Ion Complexes That Contain Ni2+, Cu2+, or Zn2+, and Histamine, as well as Adenosine 5′-Triphosphate (ATP4−) or Uridine 5′-Triphosphate (UTP4−): An Intricate Network of Equilibria. Chem Eur J 2011, 17, 5393. <http://dx.doi.org/10.1002/chem.201001931>
  • Neelakantan M. A., Sundaram M., Sivasankaran Nair M.: Solution Equilibria of Ni(II), Cu(II), and Zn(II) Complexes Involving Pyridoxine and Imidazole Containing Ligands: pH Metric, Spectral, Electrochemical, and Biological Studies. J Chem Eng Data 2011, 56, 2527. <http://dx.doi.org/10.1021/je200054w>
  • El-Sherif Ahmed A.: Coordination properties of bidentate (N,O) and tridentate (N,O,O) heterocyclic alcohols with dimethyltin(IV). J Coord Chem 2011, 64, 1240. <http://dx.doi.org/10.1080/00958972.2011.565755>
  • El-Sherif Ahmed A.: Synthesis and characterization of some potential antitumor palladium(II) complexes of 2-aminomethylbenzimidazole and amino acids. J Coord Chem 2011, 64, 2035. <http://dx.doi.org/10.1080/00958972.2011.587004>
  • Lamshöft Marc, Ivanova Bojidarka: Protonation and coordination ability of small peptides – theoretical and experimental approaches for elucidation. J Coord Chem 2011, 64, 2419. <http://dx.doi.org/10.1080/00958972.2011.598926>
  • Xue-Yi Le, Fu-Hai Wu, Xiao-Feng He, Fen-Yun Song, Liang-Nian Ji: Intramolecular stacking interaction in mixed-ligand complexes containing ATP4− and aromatic N-heterocyclic ligands. Chin J Chem 2010, 16, 356. <http://dx.doi.org/10.1002/cjoc.19980160410>
  • Xue-Yi Le, Xiao-Hua Zhou, Kai-Bei Yu, Liang-Nian Ji: Synthesis, molecular structure and intramolecular aromatic-ring stacking interaction of a novel binuclear Cu(II) complex with 1,10-phenanthroline and phenylacetate. Chin J Chem 2010, 18, 638. <http://dx.doi.org/10.1002/cjoc.20000180435>
  • El-Sherif Ahmed A., Shoukry Mohamed M., El-Bahnasawy Ramadan M., Ahmed Dalia M.: Complex formation reactions of palladium(II)-1,3-diaminopropane with various biologically relevant ligands. Kinetics of hydrolysis of glycine methyl ester through complex formation. cent eur j chem 2010, 8, 919. <http://dx.doi.org/10.2478/s11532-010-0057-4>
  • Furler Maya, Knobloch Bernd, Sigel Roland K.O.: Influence of decreased solvent permittivity on the structure and magnesium(II)-binding properties of the catalytic domain 5 of a group II intron ribozyme. Inorg Chim Ada 2009, 362, 771. <http://dx.doi.org/10.1016/j.ica.2008.03.095>
  • Sigel Helmut, Operschall Bert P., Griesser Rolf: Xanthosine 5′-monophosphate (XMP). Acid–base and metal ion-binding properties of a chameleon-like nucleotide. Chem Soc Rev 2009, 38, 2465. <http://dx.doi.org/10.1039/b902181g>
  • Shimazaki Yuichi, Takani Masako, Yamauchi Osamu: Metal complexes of amino acids and amino acid side chain groups. Structures and properties. Dalton Trans 2009, 7854. <http://dx.doi.org/10.1039/b905871k>
  • Operschall Bert P., Bianchi Emanuela M., Griesser Rolf, Sigel Helmut: Influence of decreasing solvent polarity (1,4-dioxane/water mixtures) on the stability and structure of complexes formed by copper(II), 2,2′-bipyridine or 1,10-phenanthroline and guanosine 5′-diphosphate: evaluation of isomeric equilibria† ‡. J Coord Chem 2009, 62, 23. <http://dx.doi.org/10.1080/00958970802474888>
  • Terrón Angel, Fiol Juan J., García-Raso Angel, Barceló-Oliver Miquel, Moreno Virtudes: Biological recognition patterns implicated by the formation and stability of ternary metal ion complexes of low-molecular-weight formed with amino acid/peptides and nucleobases/nucleosides. Coord Chem Rev - 2007, 251, 1973. <http://dx.doi.org/10.1016/j.ccr.2007.03.006>
  • Taha Mohamed, Saqr Rashad A., Ahmed Alaa T.: Thermodynamic studies on complexation of divalent transition metal ions with some zwitterionic buffers for biochemical and physiological research. K J CHEM THERMODYN 2007, 39, 304. <http://dx.doi.org/10.1016/j.jct.2006.06.012>
  • Mohamed Mahmoud M.A., Abd-Alla Elham M., El-Badawy Ahmed El-Sayed: Dimethyltin(IV) complexes with zwitterionic buffers (Mes and Mops). J Organomet Chem 2007, 692, 1735. <http://dx.doi.org/10.1016/j.jorganchem.2006.12.035>
  • Mohamed Mahmoud M. A.: Equilibrium studies, synthesis and characterisation of zwitterionic buffer (HEPES and HEPPS) dimethyltin(IV) complexes. Main Group Chem 2007, 6, 63. <http://dx.doi.org/10.1080/10241220701786701>
  • Sigel Helmut, Operschall Bert P., Massoud Salah S., Song Bin, Griesser Rolf: Evidence for intramolecular aromatic-ring stacking in the physiological pH range of the monodeprotonated xanthine residue in mixed-ligand complexes containing xanthosinate 5?-monophosphate (XMP). Dalton Trans 2006, 5521. <http://dx.doi.org/10.1039/b610082a>
  • Guan W., Ge C. H., Zhang X. D., Tong J., Liu Q. T.: Interaction between ligands in ternary complexes of cadmium(II) with phenanthroline and phenylalkylmalonates in solution. RUCO 2006, 32, 811. <http://dx.doi.org/10.1134/S1070328406110078>
  • Bianchi Emanuela M., Griesser Rolf, Sigel Helmut: Influence of Decreasing Solvent Polarity (1,4-Dioxane/Water Mixtures) on the Acid-Base and Copper(II)-Binding Properties of Guanosine 5′-Diphosphate. HCA 2005, 88, 406. <http://dx.doi.org/10.1002/hlca.200590026>
  • Sigel Helmut, Griesser Rolf: Nucleoside 5′-triphosphates: self-association, acid–base, and metal ion-binding properties in solution. Chem Soc Rev 2005, 34, 875. <http://dx.doi.org/10.1039/b505986k>
  • Shoukry Mohamed M., Shehata Mohamed R., Hamza Mohamed S. A., van Eldik Rudi: Equilibrium, kinetic and solvent effect studies on the reactions of [RuIII(Hedta)(H2O)] with thiols. Dalton Trans 2005, 3921. <http://dx.doi.org/10.1039/b510553f>
  • Hua Zhou Xiao, Yi Le Xue, Chen Shi: Synthesis, crystal structure and properties of a one-dimensional L-valinate bridged coordination polymer: [Cu2(L-val)2(bpy)2] n ·2nClO4·2nH2O. J Coord Chem 2005, 58, 993. <http://dx.doi.org/10.1080/00958970500038191>
  • Tovar-Tovar Araceli, Ruiz-Ramı́rez Lena, Campero Antonio, Romerosa Antonio, Moreno-Esparza Rafael, Rosales-Hoz Maria J.: Structural and reactivity studies on 4,4′-dimethyl-2,2′-bipyridine acetylacetonate copper(II) nitrate (CASIOPEINA III-ia®) with methionine, by UV–visible and EPR techniques. J  Inorg Biochem 2004, 98, 1045. <http://dx.doi.org/10.1016/j.jinorgbio.2004.02.023>
  • Da Costa Carla P., Okruszek Andrzej, Sigel Helmut: Complex Formation of Divalent Metal Ions with Uridine 5′-O-Thiomonophosphate or Methyl Thiophosphate: Comparison of Complex Stabilities with Those of the Parent Phosphate Ligands. Chem Eur J of Chem Bio 2003, 4, 593. <http://dx.doi.org/10.1002/cbic.200200551>
  • Fernández-Botello Alfonso, Holý Antonı́n, Moreno Virtudes, Sigel Helmut: Stability and structure of binary and ternary metal ion complexes in aqueous solution of the quaternary 1-[2-(phosphonomethoxy)ethyl] derivative of 2,4-diaminopyrimidine (PMEDAPy−). Properties of an acyclic nucleotide analogue. J Polyhedron 2003, 22, 1067. <http://dx.doi.org/10.1016/S0277-5387(03)00093-7>
  • Fernández-Botello Alfonso, Gómez-Coca Raquel B., Holý Antonı́n, Moreno Virtudes, Sigel Helmut: Metal-ion binding properties of O-phosphonatomethylcholine (PMCh−). Inorg Chim Ada 2002, 331, 109. <http://dx.doi.org/10.1016/S0020-1693(01)00763-0>
  • Mohamed Mahmoud M. A., Shehata Mohamed R., Shoukry Mohamed M.: TRIMETHYLTIN(IV) COMPLEXES WITH SOME SELECTED DNA CONSTITUENTS. J Coord Chem 2001, 53, 125. <http://dx.doi.org/10.1080/00958970108022607>
  • Yamauchi Osamu, Odani Akira, Hirota Shun: Metal Ion-Assisted Weak Interactions Involving Biological Molecules. From Small Complexes to Metalloproteins. Bull Chem Soc Jpn 2001, 74, 1525. <http://dx.doi.org/10.1246/bcsj.74.1525>
  • Sigel Helmut, Kapinos Larisa E.: Quantification of isomeric equilibria for metal ion complexes formed in solution by phosphate or phosphonate ligands with a weakly coordinating second site. Coord Chem Rev - 2000, 200-202, 563. <http://dx.doi.org/10.1016/S0010-8545(00)00307-6>
  • Bianchi Emanuela M., Sajadi S.Ali A., Song Bin, Sigel Helmut: Intramolecular stacking interactions in mixed ligand complexes formed by copper(II), 2,2′-bipyridine or 1,10-phenanthroline, and monoprotonated or deprotonated adenosine 5′-diphosphate (ADP3−). Evaluation of isomeric equilibria. Inorg Chim Ada 2000, 300-302, 487. <http://dx.doi.org/10.1016/S0020-1693(99)00555-1>
  • Song Bin, Sajadi S. Ali A., Gregáň Fridrich, Prónayová Nadja, Sigel Helmut: Stability of binary and ternary copper(II) complexes of the diphosphate analogue, methylphosphonylphosphate, in aqueous solution. Inorg Chim Ada 1998, 273, 101. <http://dx.doi.org/10.1016/S0020-1693(97)05917-3>
  • Sajadi S. Ali A., Song Bin, Sigel Helmut: Ternary complexes in solution. Intramolecular stacking interactions in mixed ligand complexes formed by copper(II), 2,2′-bipyridyl or 1,10-phenanthroline and a pyrimidine-nucleoside 5′-diphosphate (CDP3−, UDP3−, dTDP3−). Inorg Chim Ada 1998, 283, 193. <http://dx.doi.org/10.1016/S0020-1693(98)00097-8>
  • Lin Hua-Kuan, Zhu Shou-Rong, Zhou Zhi-Fen, Su Xun-Cheng, Gu Zong-Xin, Chen Yun-Ti: Calorimetric determination of the enthalpies of coordination of competitive ternary mixed-ligand complex compounds. Copper(II)-12-(2′-hydroxy-5′-bromo-benzyl)-1,4,7,10-tetraazacyclo-tridecane-11,13-dione-α-aminoacids and 5-substituted 1,10-phenanthrolines systems. J Polyhedron 1998, 17, 2363. <http://dx.doi.org/10.1016/S0277-5387(97)00445-2>
  • Blindauer Claudia A., Emwas Abdul H., Holý Antonín, Dvořáková Hana, Sletten Einar, Sigel Helmut: Complex Formation of the Antiviral 9-[2-(Phosphonomethoxy)Ethyl]Adenine (PMEA) and of Its N 1, N 3, and N 7 Deaza Derivatives with Copper(II) in Aqueous Solution. Chem Eur J 1997, 3, 1526. <http://dx.doi.org/10.1002/chem.19970030922>
  • Bastian Matthias, Sigel Helmut: The self-association of flavin mononucleotide (FMN2−) as determined by 1H NMR shift measurements. biophys chem 1997, 67, 27. <http://dx.doi.org/10.1016/S0301-4622(97)00012-4>
  • Shoukry, Μ.M., Mohamed, Μ.Μ.H.: EQUILIBRIUM STUDIES OF DIBUTYLTIN(IV) COMPLEXES WITH AMINO ACIDS AND PEPTIDES. MGMC 1997, 20, 281. <http://dx.doi.org/10.1515/MGMC.1997.20.5.281>
  • Zhao Jing, Song Bin, Saha Nityananda, Saha Arati, Gregńň Fridrich, Bastian Matthias, Sigel Helmut: Ternary complexes in solution1 with hydrogen phosphate and methyl phosphate as ligands. Inorg Chim Ada 1996, 250, 185. <http://dx.doi.org/10.1016/S0020-1693(96)05227-9>
  • Noethig-Laslo V., Paulić N.: EPR Spectra of Copper(II) Complexes with N,N-Dialkyl Amino Acids. The Influence of Water dissolved in Organic Solvents on the Copper(II) Coordination Sphere. Z anorg allg Chem 1995, 621, 84. <http://dx.doi.org/10.1002/zaac.19956210115>
  • Sigel Helmut: Intramolecular equilibria in metal ion complexes of artificial nucleotide analogues with antiviral properties. A case study. Coord Chem Rev - 1995, 144, 287. <http://dx.doi.org/10.1016/0010-8545(95)01158-L>
  • Sigel Helmut, Song Bin, Liang Guogang, Halbach Ralf, Felder Marcel, Bastian Matthias: Acid-base and metal ion-binding properties of flavin mononucleotide (FMN2−). Is a ‘dielectric’ effect responsible for the increased complex stability?. Inorg Chim Ada 1995, 240, 313. <http://dx.doi.org/10.1016/0020-1693(95)04548-1>
  • Scrimin Paolo, Tecilla Paolo, Tonellato Umberto: Chiral lipophilic ligands. 2. Cu(II)-Mediated transport of α-amino acids across a bulk chloroform membrane. Tetrahedron 1995, 51, 217. <http://dx.doi.org/10.1016/0040-4020(94)00935-N>
  • Nishio Motohiro, Umezawa Yoji, Hirota Minoru, Takeuchi Yasuo: The CH/π interaction: Significance in molecular recognition. Tetrahedron 1995, 51, 8665. <http://dx.doi.org/10.1016/0040-4020(94)01066-9>
  • Lomozik Lechoslaw, Odani Akira, Yamauchi Osamu: Spectroscopic studies on complex formation and non-covalent interactions in ternary palladium(II) systems involving spermidine and 2,3-diaminoproprionate or 2,4-diaminobutyrate. Inorg Chim Ada 1994, 219, 107. <http://dx.doi.org/10.1016/0020-1693(94)03837-6>
  • Sugimori Tamotsu, Masuda Hideki, Yamauchi Osamu: Structures and Properties of Ternary Copper(II) Complexes Involving a Halogen Substituted Phenylalanine and 2,2'-Bipyridine. Intermolecular Interactions between Halo and Organic Groups. Bull Chem Soc Jpn 1994, 67, 131. <http://dx.doi.org/10.1246/bcsj.67.131>
  • Lin Huakuan, Gu Zongxin, Chen Yunti: A calorimetric study of the protonation of vitamin D3 and of three other ligands and their formation of binary and ternary complexes with Cd(II). Thermochimica 1993, 219, 115. <http://dx.doi.org/10.1016/0040-6031(93)80488-V>
  • Lever A.B.P: Frontiers of the chemistry of metal ions approaching the year 2000. Coord Chem Rev - 1991, 110, 275. <http://dx.doi.org/10.1016/0010-8545(91)80008-2>
  • Masuda Hideki, Sugimori Tamotsu, Odani Akira, Yamauchi Osamu: Structural evidence for the intramolecular charge-transfer interaction involving an indole ring in ternary copper(II) complexes with L-tryptophan and aromatic diamines. Inorg Chim Ada 1991, 180, 73. <http://dx.doi.org/10.1016/S0020-1693(00)83068-6>
  • Toscano Paul J., Belsky Kimberly A., Hsieh Tze-Chen, Nicholson Terrence, Zubieta Jon: Synthesis, characterization and stereochemical preferences of cobalt(II) ternary amino acid complexes containing N-((2-pyridyl)methyl)- 2((2-aminoethyl)thio)acetamide, a stereospecific linear NSNN tetradentate ligand. J Polyhedron 1991, 10, 977. <http://dx.doi.org/10.1016/S0277-5387(00)86918-1>
  • Bastian Matthias, Sigel Helmut: Stability and Structure of Binary and Ternary Metal Ion Complexes of Orotidinate 5′-Monophosphate (OMP3-) in Aqueous Solution. J Coord Chem 1991, 23, 137. <http://dx.doi.org/10.1080/00958979109408247>
  • CORFU Nicolas A., SIGEL Helmut: Acid-base properties of nucleosides and nucleotides as a function of concentration. Comparison of the proton affinity of the nucleic base residues in the monomeric and self-associated, oligomeric 5'-triphosphates of inosine (ITP), guanosine (GTP), and adenosine (ATP). Eur J Biochem 1991, 199, 659. <http://dx.doi.org/10.1111/j.1432-1033.1991.tb16168.x>
  • Bastian Matthias, Sigel Helmut: On the metal ion binding properties of orotidine. Inorg Chim Ada 1990, 178, 249. <http://dx.doi.org/10.1016/S0020-1693(00)86789-4>
  • Zhou Xia Ying, Kostić Nenad M.: Steric effects on the selectivity of protein labelling with chelate complexes of platinum(II). J Polyhedron 1990, 9, 1975. <http://dx.doi.org/10.1016/S0277-5387(00)84010-3>
  • Sigel Helmut, Tribolet Roger, Yamauchi Osamu: The Imidazole Group and Its Stacking Properties in Mixed Ligand Metal Ion Complexes. Comments Inorg Chem 1990, 9, 305. <http://dx.doi.org/10.1080/02603599008035813>
  • MASSOUD Salah S., TRIBOLET Roger, SIGEL Helmut: Metal-ion-governed molecular recognition: extent of intramolecular stack formation in mixed-ligand-copper(II) complexes containing a heteroaromatic N base and an adenosine monophosphate (2'AMP, 3'AMP, or 5'AMP). A structuring effect of the metal-ion bridge. Eur J Biochem 1990, 187, 387. <http://dx.doi.org/10.1111/j.1432-1033.1990.tb15316.x>
  • CORFU Nicolas A., TRIBOLET Roger, SIGEL Helmut: Comparison of the self-association properties of the 5'-triphosphates of inosine (ITP), guanosine (GTP), and adenosine (ATP). Further evidence for ionic interactions in the highly stable dimeric [H2(ATP)]4-2 stack. Eur J Biochem 1990, 191, 721. <http://dx.doi.org/10.1111/j.1432-1033.1990.tb19181.x>
  • S. Massoud Salah, Sigel Helmut: Ternary complexes in solution. Part 51. Intramolecular hydrophobic and stacking interactions in mixed ligand complexes containing Cu(II), 2,2′-bipyridyl or 1,10-phenanthroline, and a simple phosphate monoester, D-ribose 5′-monophosphate or a nucleoside 5′-monophosphate (CMP, UMP, TMP, TuMP) with a non-coordinating base residue. Inorg Chim Ada 1989, 159, 243. <http://dx.doi.org/10.1016/S0020-1693(00)80574-5>