Artificial dinuclear phosphoesterases

Current Opinion in Chemical Biology

Volumn 1, Issue 4, 1997, Pages 514-521

  Chin, Jik ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; LANTHANIDE; METAL; ORGANOPHOSPHATE; PHOSPHATASE; RNA;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROLYSIS; METABOLISM; REVIEW;

CATALYSIS; DNA; HYDROLYSIS; METALS; METALS, RARE EARTH; MODELS, MOLECULAR; PHOSPHORIC ACID ESTERS; PHOSPHORIC MONOESTER HYDROLASES; RNA;

EID: 0031320341     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(97)80046-4     Document Type: Article

References (50)

1. Sträler N, Lipscomb WN, Klabunde T, Krebs B: Two-metal catalysis in enzymatic acyl- and phosphoryl-transfer reactions. Angew Chem Int Ed 1996, 35:2024-2055.
2. Wilcox DE: Binuclear metallohydrolases. Chem Rev 1996, 96:2435-2458.
3. Hall J, Hüsken D, Pieles U, Moser HE, Häner R: Efficient sequence specific cleavage of RNA using novel europium complexes conjugated to oligonucleotides. Chem Biol 1994, 1:185-190.
4. Magda D, Miller RA, Sessler JL, Iverson BL: Site-specific hydrolysis of RNA by Europium (III) texaphyrin conjugated to a synthetic oligonucleotide. J Am Chem Soc 1994, 116:7439-7440.
5. Bashkin JK, Frolova El, Sampath US: Sequence-specific cleavage of HIV mRNA by a ribozyme mimic. J Am Chem Soc 1994, 116:5981-5982.
6. Matsumura K, Endo M, Komiyama M: Lanthanide complexoligo - DNA hybrid for sequence-selective hydrolysis of RNA. J Chem Soc Chem Commun 1994:2019-2020.
7. Jones DR, Lindoy LF, Sargeson AM: Hydrolysis of phosphate esters bound to cobalt (III). Kinetics and mechanism of intramolecular attack of hydroxide on coordinated 4-nitrophenyl phosphate. J Am Chem Soc 1983, 105:7327-7336.
8. 2. J Am Chem Soc 1985, 107:3315-3321.
9. Hendry P, Sargeson AM: Metal ion promoted reactions of phosphate derivatives. Prog Inorg Chem 1990, 38:201-258.
10. Fife TH, Przystas T: Effects of divalent metal ions on the hydrolysis of esters of 2-(hydroxymethyl) picolinic acid. Metal ion catalysis of the carboxyl, hydroxide, and water reactions. J Am Chem Soc 1982, 104:2251-2257.
11. Browne KA, Bruice TC: Chemistry of phosphodiesters, DNA and models. 2. The hydrolysis of Bis(8-hydroxyquinoline) phosphate in the absence and presence of metal ions. J Am Chem Soc 1992, 114:4951.
12. Chin J: Developing artificial hydrolytic metalloenzymes by a unified mechanistic approach. Accounts Chem Res 1991, 24:145-152.
13. Vance DH, Czarnik AW: Functional group convergency in a binuclear dephosphorylation reagent J Am Chem Soc 1993, 115:12165-12166.
14. Chapman WH, Breslow R, Selective hydrolysis of phosphate esters, nitrophenyl phosphates and UpU, by dimeric zinc complexes depends on the spacer length. J Am Chem Soc 1995, 117:5462-5469.
15. Gultneh Y, Allwar R, Ahvazi B, Blaise D, Butcher RJ, Jasinski J, Jasinski J: Synthesis, reactions and structure of a hydroxobridged dinuclear Zn(II) complex: modelling the hydrolytic zinc enzymes. Inorg Chim Acta 1996, 241:31-38.
16. Koike T, Inoue M, Kimura E, Shiro M: Novel properties of cooperative oligonuclear zinc(II) ions: the selective recognition of phosphatemonoesters and their P-O ester bond cleavage by a new dinuclear zinc(II) cryptate. J Am Chem Soc 1996, 118:3091-3099.
17. Burstyn JN, Deal KA: Selective catalytic hydrolysis of a simple phosphodiester by a macrocyclic copper (II) complex. Inorg Chem 1993, 32:3585-3586.
18. Yashiro M, Ishikubo A, Komiyama M: Preparation and study of a dinuclear zinc (II) complex for the efficient hydrolysis of the phosphodiester linkage in a diribonucleotide. J Chem Soc Chem Commun 1995:1793-1794.
19. Molenveld P, Kapsabelis S, Engbersen JFJ, Reinhoudt DN: Highly efficient phosphate diester transesterification by a calix [4] arene-based dinuclear zinc (III) catalyst J Am Chem Soc 1997, 119:2948-2949. The authors have proposed a different mechanism for the cleavage of an RNA model (HPNP) but their proposal does not take into consideration the tighter binding of the phosphate to the dinuclear complex.
20. Yashiro M, Ishikubo A, Komiyama M: Efficient and unique cooperation of three zinc(II) ions in the hydrolysis of diribonucleotides by a trinuclear zinc(II) complex. J Chem Commun 1997:83-84.
21. Kimura E, Aoki S, Koike T, Shiro M: A tris (ZnII-1,4,7,10-tetraazacyclododecane) complex as a new receptor for phosphate dianions in aqueous solution. J Am Chem Soc 1997, 119:3068-3076.
22. Ragunathan KG, Schneider H-J: Binuclear lanthanide complexes as catalysts for the hydrolysis of bis(p-nitrophenyl)phosphate and double-stranded DNA. Angew Chem Int Ed 1996, 35:1219-1221.
23. Wahnon D, Lebuis A-M, Chin J: Hydrolysis of a phosphate diester coordinated to a dinuclear cobalt (III) complex: a novel mechanism. Angew Chem Int Ed 1995, 34:2412-2414.
24. Seo JS, Sung N-D, Hynes RC, Chin J: Structure and reactivity of a dinuclear cobalt (III) complex with a bridging phosphate monoester. Inorg Chem 1996, 35:7472-7473.
25. Young MJ, Chin J: Dinuclear copper (II) complex that hydrolyzes RNA. J Am Chem Soc 1995, 117:10577-10578. Crystal structure of III-3 can be found in the PhD thesis of MJ Young, 1996, McGill University [26]. The structure actually has two bridging phosphinates. One has been omitted in Figure 3 for clarity.
26. Young MJ: Phosphate diester cleavage mediated by transition metal complexes [PhD thesis]. Montreal: McGill University; 1996.
27. Bazzicalupi C, Bencini A, Bianchi A, Fusi V, Giorgi C, Paoletti P, Valtancoli B, Zanchi D. Inorg Chem 1997, 36:2784-2785.
28. Yun JW, Tanase T, Lippard SJ: Carboxylate- and phosphate ester-bridged dimagnesium (II). Dizinc(II), and dicalcium(II) complexes. Models for intermediates in biological phosphate hydrolysis. Inorg Chem 1996, 35:7590-7600.
29. Williams N, Chin J: Metal-ion catalyzed phosphate diester transesterification: quantifying double Lewis-acid activation. J Chem Commun 1996:131-132.
30. Hendry P, Sargeson AM: Reactivity of coordinated phosphate esters: pentaaminecobalt(III) complexes. Inorg Chem, 1990, 29:92-97.
31. Wall M, Hynes RC, Chin J: Double Lewis acid activation in phosphate diester cleavage. Angew Chem Int Ed, 1993, 32:1633-1635.
32. Davis AM, Hall AD, Williams A: Charge description of base-catalysed alcoholsis of aryl phosphodieaters: a ribonuclease model. J Am Chem Soc 1988, 110:5105-5108.
33. Morrow JR, Buttrey LA, Berback KA: Transesterification of a phosphate diester by divalent and trivalent metal. Inorg Chem 1992, 31:16-20.
34. Schneider H-J, Rammo J, Hettich R: Catalysis of the hydrolysis of ohosphoric acid diesters by lanthanide ions and the influence of ligands. Angew Chem Int Ed 1993, 32:1716-1719.
35. Morrow JR, Amin S, Lake CH, Churchill MR: Synthesis, structure and dynamic properties of lanthanum (III) complex of 1,4,7,10-tetrakis (2-carbamoylethyl)-1,4,7,10-tetraazacyclododecane. Inorg Chem 1993, 32:4566-4572.
36. Morrow JR, Chin AO: Synthesis and dynamic properties of kinetically inert lanthanum (III) compounds: lanthanum (III) and uropium(III) compexes of tetrakis(2-hydroxyethyl)-1,4,7,10-tetraazacyclododecane. Inorg Chem 1993, 32:3357-3361.
37. Eichhorn GL, Butzow JJ: Interactions of metal ions with polynucleotides and realted compounds. III. Degradation of polyribronucleotides by lanthanum ions. Biopolymers 1965, 3:79-94.
38. Morrow JR, Buttrey LA, Shelton VM, Berback KA: Efficient catalytic cleavage of RNA by lanthanide (III) macrocyclic complexes: towards synthetic nucleases for in vivo applications. J Am Chem Soc 1992, 114:1903-1905.
39. 2+ and lanthanides, on the cleavage of ribonucleotides and RNA model compounds. Proc Natl Acad Sci USA 1991, 88:4080-4083.
40. 2. Angew Chem Int Ed 1994, 33:773-775.
41. Komiyama M, Matsumara K, Matsumoto Y: Unprecedentedly fast hydrolysis of the RNA dinucleoside monophosphate ApA and UpU by rare earth metal ions. J Chem Soc Chem Commun 1992:640-641.
42. Takasaki BK, Chin J: Synergistic effect between La(III) and hydrogen peroxide in phosphate cleavage. J Am Chem Soc 1993, 115:9337-9338.
43. Takasaki BK, Chin J: La (III)-hydrogen peroxide cooperativity in phosphate diester cleavage: a mechanistic study. J Am Chem Soc 1995, 117:8582-8585.
44. Komiyama M, Kamitani J, Sumaoka J, Asanuma H: RNA hydrolysis by the combination of the lanthanum (III) ion and hydrogen peroxide. Chem Lett 1996:869-870.
45. Hurst P, Takasaki BK, Chin J: Rapid cleavage of RNA with a La(III) dimer. J Am Chem Soc 1996, 118:9982-9983.
46. Takasaki BK, Chin J: Cleavage of the phosphate diester backbone of DNA with cerbium(III) and molecular oxygen. J Am Chem Soc 1994, 116:1121-1122.
47. 2O. Inorg Chim Acta 1987, 126:L3.
48. Takeda N, Imai T, Irisawa M, Sumaoka J, Yashiro M, Shigekawa H, Komiyama M: Chem Lett 1996:599-600.
49. Irisawa M, Takeda N, Komiyama M: Synergetic catalysis by two non-ianthanide metal ions for hydrolysis of diribonucleotides. J Chem Commun 1995:1221-1228.
50. 13) rate enhancement in phosphonate ester hydrolysis catalyzed by two metal ions. J Am Chem Soc 1994, 116:11614-11615.