Effects of Intermediates between Vitamins K 2 and K 3 on Mammalian DNA polymerase inhibition and anti-inflammatory activity

International Journal of Molecular Sciences

Volumn 12, Issue 2, 2011, Pages 1115-1132

  Mizushina, Yoshiyuki ^a   Maeda, Jun ^b   Irino, Yasuhiro ^b   Nishida, Masayuki ^b   Nishiumi, Shin ^b   Kondo, Yasuyuki ^b   Nishio, Kazuyuki ^c   Kuramochi, Kouji ^c   Tsubaki, Kazunori ^c   Kuriyama, Isoko ^a   Azuma, Takeshi ^b   Yoshida, Hiromi ^a   Yoshida, Masaru ^b  

^a KOBE GAKUIN UNIVERSITY   (Japan)

^b KOBE UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

^c KYOTO PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Anti inflammation; DNA polymerase ; Enzyme inhibitor; MK 2; Vitamin K

Indexed keywords

ANTIINFLAMMATORY AGENT; DEOXYRIBONUCLEASE; DNA DIRECTED DNA POLYMERASE ALPHA; DNA POLYMERASE; DNA POLYMERASE KAPPA; DNA POLYMERASE LAMBDA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LIPOPOLYSACCHARIDE; MENADIONE; MENATETRENONE; MK 1; MK 2; MK 3; NUCLEOTIDYLTRANSFERASE; PHORBOL 13 ACETATE 12 MYRISTATE; POLYNUCLEOTIDE 5' HYDROXYL KINASE; RNA POLYMERASE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; DNA DIRECTED DNA POLYMERASE; DNA DIRECTED DNA POLYMERASE GAMMA; FARNOQUINONE;

ANIMAL CELL; ANIMAL CELL CULTURE; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BODY WEIGHT; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; FEMALE; GENE REPRESSION; IC 50; IN VITRO STUDY; IN VIVO STUDY; MACROPHAGE ACTIVATION; MOUSE; NONHUMAN; OTITIS; ANALOGS AND DERIVATIVES; ANIMAL; BOVINAE; CELL LINE; DRUG EFFECTS; HUMAN; MACROPHAGE; METABOLISM; SPECIES DIFFERENCE;

ANIMALIA; MAMMALIA; MUS; PROKARYOTA;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CATTLE; CELL LINE; DNA-DIRECTED DNA POLYMERASE; HUMANS; MACROPHAGES; MICE; NF-KAPPA B; OTITIS; SPECIES SPECIFICITY; TUMOR NECROSIS FACTOR-ALPHA; VITAMIN K 2; VITAMIN K 3;

EID: 79952291166     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms12021115     Document Type: Article

References (54)

1. Hubscher, U.; Maga, G.; Spadari, S. Eukaryotic DNA polymerases. Annu. Rev. Biochem. 2002, 71, 133-163.
2. Bebenek, K.; Kunkel, T.A. DNA repair and replication. In Advances in Protein Chemistry; Yang, W., Ed.; Elsevier: San Diego, CA, USA, 2004; Volume 69, pp. 137-165.
3. Takata, K.; Shimizu, T.; Iwai, S.; Wood, R.D. Human DNA polymerase N (POLN) is a low fidelity enzyme capable of error-free bypass of 5S-thymine glycol. J. Biol. Chem. 2006, 281, 23445-23455.
4. Friedberg, E.C.; Feaver, W.J.; Gerlach, V.L. The many faces of DNA polymerases: strategies for mutagenesis and for mutational avoidance. Proc. Natl. Acad. Sci. USA 2000, 97, 5681-5683.
5. Sakaguchi, K.; Sugawara, F.; Mizushina, Y. Inhibitors of eukaryotic DNA polymerases. Seikagaku 2002, 74, 244-251.
6. Mizushina, Y. Specific inhibitors of mammalian DNA polymerase species. Biosci. Biotechnol. Biochem. 2009, 73, 1239-1251.
7. 3 induces mitochondria-mediated cytotoxicity in human cancer cells. Cancer Sci. 2008, 99, 1040-1048.
8. 3 on DNA polymerase and angiogenesis. Int. J. Mol. Med. 2008, 22, 381-387.
9. Tanaka, S.; Nishiumi, S.; Nishida, M.; Mizushina, Y.; Kobayashi, K.; Masuda, A.; Fujita, T.; Morita, Y.; Mizuno, S.; Kutsumi, H.; Azuma, T.; Yoshida, M. Vitamin K3 attenuates lipopolysaccharide-induced acute lung injury through inhibition of nuclear factor-.B activation. Clin. Exp. Immunol. 2010, 160, 283-292.
10. 3 attenuates cerulein-induced acute pancreatitis through inhibition of the autophagic pathway. Pancreas 2010, 40, 84-94.
11. Seegers, W.H.; Bang, N.U. Blood Clotting Enzymology; Academic Press: New York, NY, USA, 1967.
12. Billeter, M.; Bolliger, W.; Martius, C. Untersuchungen uber die umwandlung von verfutterten K-vitamin durch austausch der seitenkette und die rolle der darmbakterien hierbei. Biochem. Z 1964, 340, 290-303.
13. Davidson, R.T.; Foley, A.L.; Engelke, J.A.; Suttie, J.W. Conversion of dietary phylloquinone to tissue menaquinone-4 in rats is not dependent on gut bacteria. J. Nutr. 1998, 128, 220-223.
14. The Merck Index; Budavari, S., O'Neil, M.J., Smith, A., Heckelman, P.E., Eds.; Merck & Co., Inc.: Rahway, NJ, USA, 1989.
15. Taggart, W.V.; Matschiner, J.T. Metabolism of menadione-6,7-3H in the rat. Biochemistry 1969, 8, 1141-1146.
16. Mizushina, Y.; Kamisuki, S.; Kasai, N.; Ishidoh, T.; Shimazaki, N.; Takemura, M.; Asahara, H.; Linn, S.; Yoshida, S.; Koiwai, O.; Sugawara, F.; Yoshida, H.; Sakaguchi, K. Petasiphenol: a DNA polymerase λ inhibitor. Biochemistry 2002, 41, 14463-14471.
17. Mizushina, Y.; Ishidoh, T.; Takeuchi, T.; Shimazaki, N.; Koiwai, O.; Kuramochi, K.; Kobayashi, S.; Sugawara, F.; Sakaguchi, K.; Yoshida, H. Monoacetylcurcumin: a new inhibitor of eukaryotic DNA polymerase λ and a new ligand for inhibitor-affinity chromatography. Biochem. Biophys. Res. Commun. 2005, 337, 1288-1295.
18. Takeuchi, T.; Ishidoh, T.; Iijima, H.; Kuriyama, I.; Shimazaki, N.; Koiwai, O.; Kuramochi, K.; Kobayashi, S.; Sugawara, F.; Sakaguchi, K.; Yoshida, H.; Mizushina, Y. Structural relationship of curcumin derivatives binding to the BRCT domain of human DNA polymerase. Genes Cells 2006, 11, 223-235.
19. Mizushina, Y.; Hirota, M.; Murakami, C.; Ishidoh, T.; Kamisuki, S.; Shimazaki, N.; Takemura, M.; Perpelescu, M.; Suzuki, M.; Yoshida, H.; Sugawara, F.; Koiwai, O.; Sakaguchi, K. Some anti-chronic inflammatory compounds are DNA polymerase λ-specific inhibitors. Biochem. Pharmacol. 2003, 66, 1935-1944.
20. Mizushina, Y.; Takeuchi, T.; Kuramochi, K.; Kobayashi, S.; Sugawara, F.; Sakaguchi, K.; Yoshida, H. Study on the molecular structure and bio-activity (DNA polymerase inhibitory activity, anti-inflammatory activity and anti-oxidant activity) relationship of curcumin derivatives. Curr. Bioactive Compd. 2007, 3, 171-177.
21. Nishida, M.; Nishiumi, S.; Mizushina, Y.; Fujishima, Y.; Yamamoto, K.; Masuda, A.; Mizuno, S.; Fujita, T.; Morita, Y.; Kutsumi, H.; Yoshida, H.; Azuma, T.; Yoshida, M. Monoacetylcurcumin strongly regulates inflammatory responses through inhibition of NF-.B activation. Int. J. Mol. Med. 2010, 25, 761-767.
22. Hecker, E. Carcinogenesis; Raven Press: New York, NY, USA, 1978; pp. 11-48.
23. Fujiki, H.; Sugimura, T. Advances in Cancer Research; Academic Press, Inc.: London, UK, 1987; pp. 223-264.
24. Nakamura, Y.; Murakami, A.; Ohto, Y.; Torikai, K.; Tanaka, T.; Ohigashi, H. Suppression of tumor promoter-induced oxidative stress and inflammatory responses in mouse skin by a superoxide generation inhibitor 1'-acetoxychavicol acetate. Cancer Res. 1995, 58, 4832-4839.
25. Huang, T.T.; Wuerzberger-Davis, S.M. Sequential modification of NEMO/IKKÁ by SUMO-1 and ubiquitin mediates NF-.B activation by genotoxic stress. Cell 2003, 115, 565-576.
26. Hayden, M.S.; Ghosh, S. Signaling to NF-.B. Genes Dev. 2004, 18, 2195-2224.
27. Bonizzi, G.; Karin, M. The two NF-.B activation pathways and their role in innate and adaptive immunity. Trends Immunol. 2004, 25, 280-288.
28. Wajant, H.; Pfizenmaier, K.; Scheurich, P. Tumor necrosis factor signaling. Cell Death Differ. 2003, 10, 45-65.
29. Elson, C.O.; Sartor, R.B.; Tennyson, G.S.; Riddell, R.H. Experimental models of inflammatory bowel disease. Gastroenterology 1995, 109, 1344-1367.
30. Aggarwal, B.B. Signalling pathways of the TNF superfamily: A double-edged sword. Nat. Rev. Immunol. 2003, 3, 745-756.
31. Furie, B.; Furie, B.C. Molecular basis of vitamin K-dependent gamma-carboxylation. Blood 1990, 75, 1753-1762.
32. Suttie, J.W. Synthesis of vitamin K-dependent proteins. FASEB J. 1993, 7, 445-452.
33. Shearer, M.J. Role of vitamin K and Gla proteins in the pathophysiology of osteoporosis and vascular calcification. Curr. Opin. Clin. Nutr. Metab. Care 2000, 3, 433-438.
34. Ohsaki, Y.; Shirakawa, H.; Hiwatashi, K.; Furukawa, Y.; Mizutani, T.; Komai, M. Vitamin K suppresses lipopolysaccharide-induced inflammation in the rat. Biosci. Biotechnol. Biochem. 2006, 70, 926-932.
35. Elder, S.J.; Haytowitz, D.B.; Howe, J.; Peterson, J.W.; Booth, S.L. Vitamin K contents of meat, dairy, and fast food in the U.S. Diet. J. Agric. Food Chem. 2006, 54, 463-467.
36. Tsukamoto, Y.; Ichise, H.; Kakuda, H.; Yamaguchi, M. Intake of fermented soybean (natto) increases circulating vitamin K2 (menaquinone-7) and gamma-carboxylated osteocalcin concentration in normal individuals. J. Bone Miner. Metab. 2000, 18, 216-222.
37. Suttie, J.W. The importance of menaquinone in human nutrition. Annu. Rev. Nutr. 1995, 15, 399-417.
38. Booth, S.L. Dietary vitamin K guidance: An effective strategy for stable control of oral anticoagulation? Nutr. Rev. 2010, 68, 178-181.
39. Garcia-Diaz, M.; Bebenek, K.; Sabariegos, R.; Dominguez, O.; Rodriguez, J.; Kirchhoff, T.; Garcia-Palomero, E.; Picher, A.J.; Juarez, R.; Ruiz, J.F.; Kunkel, T.A.; Blanco, L. DNA polymerase λ, a novel DNA repair enzyme in human cells. J. Biol. Chem. 2002, 277, 13184-13191.
40. Singhal, R.K.; Wilson, S.H. Short gap-filling synthesis by DNA polymerase ß is processive. J. Biol. Chem. 1993, 268, 15906-15911.
41. Matsumoto, Y.; Kim, K. Excision of deoxyribose phosphate residues by DNA polymerase ß during DNA repair. Science 1995, 269, 699-702.
42. Sobol, R.W.; Horton, J.K.; Kuhn, R.; Gu, H.; Singhal, R.K.; Prasad, R.; Rajewsky, K.; Wilson, S.H. Requirement of mammalian DNA polymerase-ß in base-excision repair. Nature 1996, 379, 183-186.
43. Ramadan, K.; Shevelev, I.V.; Maga, G.; Hubscher, U. DNA polymerase λ from calf thymus preferentially replicates damaged DNA. J. Biol. Chem. 2002, 277, 18454-18458.
44. Sugo, N.; Aratani, Y.; Nagashima, Y.; Kubota, Y.; Koyama, H. Neonatal lethality with abnormal neurogenesis in mice deficient in DNA polymerase ß. EMBO J. 2000, 19, 1397-1404.
45. Garcia-Diaz, M.; Bebenek, K.; Kunkel, T.A.; Blanco, L. Identification of an intrinsic 5'-deoxyribose-5-phosphate lyase activity in human DNA polymerase λ: A possible role in base excision repair. J. Biol. Chem. 2001, 276, 34659-34663.
46. Hirose, F.; Hotta, Y.; Yamaguchi, M.; Matsukage, A. Difference in the expression level of DNA polymerase ß among mouse tissues: high expression in the pachytene spermatocyte. Exp. Cell Res. 1989, 181, 169-180.
47. Garcia-Diaz, M.; Dominguez, O.; Lopez-Fernandez, L.A.; De Lera, L.T.; Saniger, M.L.; Ruiz, J.F.; Parraga, M.; Garcia-Ortiz, M.J.; Kirchhoff, T.; Del Mazo, J.; Bernad, A.; Blanco, L. DNA polymerase λ, a novel DNA repair enzyme in human cells. J. Mol. Biol. 2000, 301, 851-867.
48. Bertocci, B.; de Smet, A.; Flatter, E.; Dahan, A.; Bories, J.C.; Landreau, C.; Weill, J.C.; Reynaud, C.A. Cutting edge: DNA polymerases μ and λ are dispensable for Ig gene hypermutation. J. Immunol. 2002, 168, 3702-3706.
49. Mayer, H.; Isler, O. Synthesis of vitamins K. Methods Enzymol. 1971, 18, 491-547.
50. Mizushina, Y.; Motoshima, H.; Yamaguchi, Y.; Takeuchi, T.; Hirano, K.; Sugawara, F.; Yoshida, H. 3-O-methylfunicone, a selective inhibitor of mammalian Y-family DNA polymerases from an Australian sea salt fungal strain. Mar. Drugs 2009, 7, 624-639.
51. Mizushina, Y.; Tanaka, N.; Yagi, H.; Kurosawa, T.; Onoue, M.; Seto, H.; Horie, T.; Aoyagi, N.; Yamaoka, M.; Matsukage, A.; Yoshida, S.; Sakaguchi, K. Fatty acids selectively inhibit eukaryotic DNA polymerase activities in vitro. Biochim. Biophys. Acta 1996, 1308, 256-262.
52. Mizushina, Y.; Yoshida, S.; Matsukage, A.; Sakaguchi, K. The inhibitory action of fatty acids on DNA polymerase ß. Biochim. Biophys. Acta 1997, 1336, 509-521.
53. Gschwendt, M.; Kittstein, W.; Furstenberger, G.; Marks, F. The mouse ear edema: a quantitatively evaluable assay for tumor promoting compounds and for inhibitors of tumor promotion. Cancer Lett. 1984, 25, 177-185.
54. Medeiros, R.; Otuki, M.F.; Avellar, M.C.; Calixto, J.B. Mechanisms underlying the inhibitory actions of the pentacyclic triterpene a-amyrin in the mouse skin inflammation induced by phorbol ester 12-O-tetradecanoylphorbol-13-acetate. Eur. J. Pharmacol. 2007, 559, 227-235.