The effect of divalent cations on the catalytic activity of the human plasma 3′-exonuclease

BioMetals

Volumn 23, Issue 6, 2010, Pages 1113-1121

  Wojcik, Marzena ^b   Stec, Wojciech J ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b NONE

Author keywords

Catalysis; NPP1; Phosphorothioates; The human plasma 3 exonuclease

Indexed keywords

CADMIUM; CALCIUM ION; COBALT; DIVALENT CATION; EDETIC ACID; MAGNESIUM ION; MANGANESE; NICKEL; OLIGONUCLEOTIDE PHOSPHOROTHIOATE; PHOSPHODIESTERASE; SPLEEN EXONUCLEASE;

ARTICLE; BINDING SITE; BIOCATALYSIS; CHEMICAL BOND; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME BLOOD LEVEL; ENZYME CONFORMATION; ENZYME DEGRADATION; ENZYME SPECIFICITY; ENZYME STABILITY; ENZYME SUBSTRATE COMPLEX; HUMAN; METAL BINDING; PROTEIN HYDROLYSIS;

CATALYSIS; CATIONS, DIVALENT; EDETIC ACID; EXONUCLEASES; HUMANS; MAGNESIUM; MANGANESE; MODELS, CHEMICAL; PHOSPHATES; THIONUCLEOTIDES;

EID: 78349313090     PISSN: 09660844     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10534-010-9358-5     Document Type: Article

References (41)

1. MS Abaza A Al-Saffar S Al-Sawan R Al-Attiyah 2008 c-myc antisense oligonucleotides sensitize human colorectal cancer cells to chemotherapeutic drugs Tumour Biol 29 287 303 10.1159/000156706 1:CAS:528:DC%2BD1cXhsVOgtLjF 10.1159/000156706 18802399
2. PA Bartlett F Eckstein 1982 Stereochemical course of polymerization catalyzed by avian myeloblastosis virus reverse transcriptase J Biol Chem 257 8879 8884 1:CAS:528:DyaL38XlsFyltbk%3D 6178737
3. SI Belli A Sali JW Goding 1994 Divalent cations stabilize the conformation of plasma cell membrane glycoprotein PC-1 (alkaline phosphodiesterase I) Biochem J 304 75 80 1:CAS:528:DyaK2cXmslGhtrk%3D 7998960
4. M Bollen R Gijsbers H Ceulemans W Stalmans C Stefan 2000 Nucleotide pyrophosphatases/phosphodiesterases on the move Crit Rev Biochem Mol Biol 35 393 432 10.1080/10409230091169249 1:CAS:528:DC%2BD3MXnvFagsg%3D%3D 10.1080/10409230091169249 11202013
5. MD Bond B Holmquist BL Vallee 1986 Thioamide substrate probes of metal-substrate interactions in carboxypeptidase A catalysis J Inorg Biochem 28 97 105 1:CAS:528:DyaL2sXhtFGltL0%3D 10.1016/0162-0134(86)80074-5 3806099
6. CA Brautigam TA Steitz 1998 Structural principles for the inhibition of the 3′-5′ exonuclease activity of Escherichia coli DNA polymerase I by phosphorothioates J Mol Biol 277 363 377 10.1006/jmbi.1997.1586 1:CAS:528:DyaK1cXislalsL0%3D 10.1006/jmbi.1997.1586 9514742 (Pubitemid 28174974)
7. BA Connolly F Eckstein A Pingoud 1984 The stereochemical course of the restriction endonuclease EcoRI- catalyzed reaction J Biol Chem 259 10760 10763 1:CAS:528:DyaL2cXmtVKlt7o%3D 6088516
8. JA Cowan 1998 Metal activation of enzymes in nucleic acid biochemistry Chem Rev 98 1067 1087 1:CAS:528:DyaK1cXis12iu7c%3D 10.1021/cr960436q 11848925
9. RD Duan T Bergman N Xu J Wu Y Cheng J Duan S Nelander C Palmberg A Nilsson 2003 Identification of human intestinal alkaline sphingomyelinase as a novel ecto-enzyme related to the nucleotide phosphodiesterase family J Biol Chem 278 38528 38536 10.1074/jbc.M305437200 1:CAS:528:DC%2BD3sXnslSqu7s%3D 10.1074/jbc.M305437200 12885774 (Pubitemid 37221748)
10. F Eckstein VW Armstrong H Sternbach 1976 Stereochemistry of polymerization by DNA-dependent RNA- polymerase from Escherichia coli: an investigation with a diastereomeric ATP-analogue Proc Natl Acad Sci USA 73 2987 2990 1:CAS:528:DyaE28XlsFGltbc%3D 10.1073/pnas.73.9.2987 787980
11. F Eckstein H Sternbach F von der Haar 1977 Stereochemistry of internucleotidic bond formation by tRNA nucleotidyltransferase from baker′s yeast Biochemistry 16 3429 3432 1:CAS:528:DyaE2sXkvVSgt7g%3D 10.1021/bi00634a021 329872
12. F Eckstein PM Burgers DH Hunneman 1979 Stereochemistry of hydrolysis by snake venom phosphodiesterase J Biol Chem 254 7476 7478 224029
13. PS Eder RJ DeVine JM Dagle JA Walder 1991 Substrate specificity and kinetics of degradation of antisense oligonucleotides by a 3′-exonuclease in plasma Antisense Res Dev 1 141 151 1:CAS:528:DyaK3sXitVyhtbY%3D 1841656
14. PA Frey RD Sammons 1985 Bond order and charge localization in nucleoside phosphorothioates Science 228 541 545 1:CAS:528:DyaL2MXlvFKgt7g%3D 10.1126/science.2984773 2984773
15. R Gijsbers H Ceulemans W Stalmans M Bollen 2001 Structural and catalytic similarities between nucleotide pyrophosphatases/phosphodiesterases and alkaline phosphatases J Biol Chem 276 1361 1368 10.1074/jbc.M007552200 1:CAS:528:DC%2BD3MXmtV2jug%3D%3D 10.1074/jbc.M007552200 11027689 (Pubitemid 32096567)
16. M Gilar A Belenky Y Budman DL Smisek AS Cohen 1998 Impact of 3′-exonuclease stereoselectivity on the kinetics of phosphorothioate oligonucleotide metabolism Antisense Nucleic Acids Drug Dev 8 35 42 1:CAS:528:DyaK1cXhsFymtbc%3D
17. JW Goding B Grobben H Slegers 2003 Physiological and pathophysiological functions of the ectonucleotide pyrophosphatase/phosphodiesterase family Biochim Biophys Acta 1638 1 19 10.1016/S0925-4439(03)00058-9 1:CAS:528: DC%2BD3sXjvFahsb0%3D 12757929 (Pubitemid 36577366)
18. JA Grasby BA Connolly 1992 Stereochemical outcome of the hydrolysis reaction catalyzed by the EcoRV restriction endonuclease Biochemistry 31 7855 7861 1:CAS:528:DyaK38XltVOisLg%3D 10.1021/bi00149a016 1510972
19. AP Gupta SJ Benkovic 1984 Stereochemical course of the 3′ → 5′ exonuclease activity of DNA polymerase Biochemistry 23 5874 5881 1:CAS:528:DyaL2MXisFeg 10.1021/bi00319a029 6098302
20. GD Hoke K Draper SM Freier C Gonzalez VB Driver MC Zounes DJ Ecker 1991 Effects of phosphorothioate capping on antisense oligonucleotide stability, hybridization and antiviral efficacy versus herpes simplex virus infection Nucleic Acids Res 19 5743 5748 1:CAS:528:DyaK38XnsFOgtw%3D%3D 10.1093/nar/19.20.5743 1658742
21. H Irwing RJP Williams 1953 The stability of transition metal complexes J Chem Soc 3 3192 3210 10.1039/jr9530003192
22. M Koziolkiewicz M Wojcik A Kobylanska B Karwowski B Rebowska P Guga WJ Stec 1997 Stability of stereoregular oligo (nucleoside phosphorothioate)s in human plasma: diastereoselectivity of plasma 3′-exonuclease Antisense Nucleic Acids Drug Dev 7 43 48 1:CAS:528:DyaK2sXhsVKitL0%3D
23. M Koziolkiewicz E Gendaszewska M Maszewska CA Stein WJ Stec 2001 The mononucleotide-dependent, nonantisense mechanism of action of phosphodiester and phosphorothioate oligonucleotides depends upon the activity of an ecto-5′-nucleotidase Blood 98 995 1002 10.1182/blood.V98.4.995 1:CAS:528:DC%2BD3MXmtFeis7c%3D 10.1182/blood.V98.4.995 11493444
24. M Koziolkiewicz A Owczarek M Wojcik K Domanski P Guga WJ Stec 2002 Retention of configuration in the action of human plasma 3′-exonuclease on oligo (deoxynucleoside phosphorothioate). A new method for assignment of absolute configuration at phosphorus in isotopomeric deoxyadenosine 5′-O-[18O]-phosphorothioate J Am Chem Soc 124 4623 4627 10.1021/ja017187u 1:CAS:528:DC%2BD38XitlCisrk%3D 10.1021/ja017187u 11971710 (Pubitemid 34465001)
25. A Luganini P Caposio S Landolfo G Gribaudo 2008 Phosphorothioate-modified oligodeoxynucleotides inhibit human cytomegalovirus replication by blocking virus entry Antimicrob Agents Chemother 52 1111 1120 10.1128/AAC.00987-07 1:CAS:528:DC%2BD1cXivFalt7o%3D 10.1128/AAC.00987-07 18180342 (Pubitemid 351358395)
26. B Nawrot N Paul B Rebowska WJ Stec 2008 Significance of stereochemistry of 3′-terminal phosphorothioate-modified primer in DNA polymerase-mediated chain extension Mol Biotechnol 40 119 126 10.1007/s12033-008-9096-x 1:CAS:528:DC%2BD1cXht1ais7jO 10.1007/s12033-008-9096-x 18769882
27. Y Oda MD Kuo SS Huang JS Huang 1993 The major acidic fibroblast growth factor (aFGF)-stimulated phosphoprotein from bovine liver plasma membranes has aFGF-stimulated kinase, autoadenylylation, and alkaline nucleotide phosphodiesterase activities J Biol Chem 268 27318 27326 1:CAS:528: DyaK3sXmsVWls74%3D 7505270
28. GA Orr J Simon SR Jones GJ Chin JR Knowles 1978 Adenosine 5′-O-([gamma-18O]gamma-thio)triphosphate chiral at the gamma-phosphorus: stereochemical consequences of reactions catalyzed by pyruvate kinase, glycerol kinase, and hexokinase Proc Natl Acad Sci USA 75 2230 2233 1:CAS:528: DyaE1cXltValt7g%3D 10.1073/pnas.75.5.2230 209459
29. RG Pearson 1968 Hard and soft acids and bases, HSAB, part I: fundamental principles J Chem Educ 45 581 587 1:CAS:528:DyaF1cXltVShs74%3D 10.1021/ed045p581
30. NF Rebbe BD Tong EM Finley S Hickman 1991 Identification of nucleotide pyrophosphatase/alkaline phosphodiesterase I activity associated with the mouse plasma cell differentiation antigen PC-1 Proc Natl Acad Sci USA 88 5192 5196 1:CAS:528:DyaK3MXltlSnsb4%3D 10.1073/pnas.88.12.5192 1647027
31. H Sakagami J Aoki Y Natori K Nishikawa Y Kakehi Y Natori H Arai 2005 Biochemical and molecular characterization of a novel choline-specific glycerophosphodiester phosphodiesterase belonging to the nucleotide pyrophosphatase/phosphodiesterase family J Biol Chem 280 23084 23093 10.1074/jbc.M413438200 1:CAS:528:DC%2BD2MXltVyhur4%3D 10.1074/jbc.M413438200 15788404 (Pubitemid 40853219)
32. KF Sheu PA Frey 1978 UDP-glucose pyrophosphorylase. Stereochemical course of the reaction of glucose 1- phosphate with uridine-5′ [1-thiotriphosphate] J Biol Chem 253 3378 3380 1:CAS:528:DyaE1cXltVaktr8%3D 649578
33. WJ Stec A Grajkowski A Kobylanska B Karwowski M Koziolkiewicz K Misiura A Okruszek A Wilk P Guga M Boczkowska 1995 Diastereomers of nucleoside 3-O-2-thio-1.3.2 oxathia(selena)phospholanes): building blocks for stereocontrolled synthesis of oligo(nucleoside phosphorothioate)s J Am Chem Soc 117 12020 12029 10.1021/ja00154a001 (Pubitemid 26022768)
34. C Stefan S Jansen M Bollen 2005 NPP-type ecto-phosphodiesterases: unity in diversity Trends Biochem Sci 30 542 550 10.1016/j.tibs.2005.08.005 1:CAS:528:DC%2BD2MXhtVKjsL7L 10.1016/j.tibs.2005.08.005 16125936 (Pubitemid 41356492)
35. DJ Stewart RC Donehower EA Eisenhauer N Wainman AK Shah C Bonfils AR MacLeod JM Besterman GK Reid 2003 A phase I pharmacokinetic and pharmacodynamic study of the DNA methyltransferase 1 inhibitor MG98 administered twice weekly Ann Oncol 14 766 774 10.1093/annonc/mdg216 1:STN:280:DC%2BD3s7otleitA%3D%3D 10.1093/annonc/mdg216 12702532 (Pubitemid 36621778)
36. JL Vaerman P Moureau F Deldime P Lewalle C Lammineur F Morschhauser P Martiat 1997 Antisense oligodeoxyribonucleotides suppress hematologic cell growth through stepwise release of deoxyribonucleotides Blood 90 331 339 1:CAS:528:DyaK2sXktlaqtb4%3D 9207469
37. S Wang K Karbstein A Peracchi L Beigelman D Herschlag 1999 Identification of the hammerhead ribozyme metal ion binding site responsible for rescue of the deleterious effect of a cleavage site phosphorothioate Biochemistry 38 14363 14378 10.1021/bi9913202 1:CAS:528:DyaK1MXmt12lsr4%3D 10.1021/bi9913202 10572011 (Pubitemid 29513853)
38. P-phosphorothioate modification in the precursor tRNA at the RNase P cleavage site Proc Natl Acad Sci USA 93 8924 8928 1:CAS:528:DyaK28Xlt1Ciurw%3D 10.1073/pnas.93.17.8924 8799129 (Pubitemid 26281993)
39. M Wojcik M Cieslak WJ Stec JW Goding M Koziolkiewicz 2007 Nucleotide pyrophosphatase/phosphodiesterase 1 is responsible for degradation of antisense phosphorothioate oligonucleotides Oligonucleotides 17 134 145 10.1089/oli.2007.0021 1:CAS:528:DC%2BD2sXks1ynurc%3D 10.1089/oli.2007.0021 17461770 (Pubitemid 46651435)
40. 2+ rescues in reactions catalyzed by a hammerhead ribozyme FEBS Lett 431 154 160 10.1016/S0014-5793(98)00734-0 1:CAS:528:DyaK1cXks1KqsbY%3D 10.1016/S0014- 5793(98)00734-0 9708893 (Pubitemid 28334207)
41. Zon G, Stec WJ (1991) Phosphorothioate oligonucleotides. In: Eckstein F (ed) Oligonucleotides and analogues: a practical approach. IRL Press, Oxford, pp 87-108