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Chemical Compound Review

AG-K-68782     3-methyl-2- (3,7,11,15,19,23,27,31...

Synonyms: AC1L1ANQ, CTK5J8840
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Disease relevance of vitamin K2


Psychiatry related information on vitamin K2


High impact information on vitamin K2


Chemical compound and disease context of vitamin K2


Biological context of vitamin K2


Anatomical context of vitamin K2


Associations of vitamin K2 with other chemical compounds


Gene context of vitamin K2


Analytical, diagnostic and therapeutic context of vitamin K2


  1. Oxidation of reduced menaquinone by the fumarate reductase complex in Escherichia coli requires the hydrophobic FrdD peptide. Cecchini, G., Thompson, C.R., Ackrell, B.A., Westenberg, D.J., Dean, N., Gunsalus, R.P. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  2. Essential role of Glu-C66 for menaquinol oxidation indicates transmembrane electrochemical potential generation by Wolinella succinogenes fumarate reductase. Lancaster, C.R., Gorss, R., Haas, A., Ritter, M., Mäntele, W., Simon, J., Kröger, A. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  3. Crystal structure of Mycobacterium tuberculosis MenB, a key enzyme in vitamin K2 biosynthesis. Truglio, J.J., Theis, K., Feng, Y., Gajda, R., Machutta, C., Tonge, P.J., Kisker, C. J. Biol. Chem. (2003) [Pubmed]
  4. Effect of vitamin K2 on cortical and cancellous bones in orchidectomized and/or sciatic neurectomized rats. Iwamoto, J., Yeh, J.K., Takeda, T. J. Bone Miner. Res. (2003) [Pubmed]
  5. Transient-state reduction and steady-state kinetic studies of menaquinol oxidase from Bacillus subtilis, cytochrome aa3-600 nm. Spectroscopic characterization of the steady-state species. Mattatall, N.R., Cameron, L.M., Hill, B.C. Biochemistry (2001) [Pubmed]
  6. Effect of menatetrenone (vitamin K2) treatment on bone loss in patients with anorexia nervosa. Iketani, T., Kiriike, N., Murray, n.u.l.l., Stein, B., Nagao, K., Nagata, T., Minamikawa, N., Shidao, A., Fukuhara, H. Psychiatry research. (2003) [Pubmed]
  7. X-ray structure of the membrane-bound cytochrome c quinol dehydrogenase NrfH reveals novel haem coordination. Rodrigues, M.L., Oliveira, T.F., Pereira, I.A., Archer, M. EMBO J. (2006) [Pubmed]
  8. Vitamin K2 inhibits the growth and invasiveness of hepatocellular carcinoma cells via protein kinase A activation. Otsuka, M., Kato, N., Shao, R.X., Hoshida, Y., Ijichi, H., Koike, Y., Taniguchi, H., Moriyama, M., Shiratori, Y., Kawabe, T., Omata, M. Hepatology (2004) [Pubmed]
  9. The growth inhibitory effects of vitamins K and their actions on gene expression. Wang, Z., Wang, M., Finn, F., Carr, B.I. Hepatology (1995) [Pubmed]
  10. Steroid and xenobiotic receptor SXR mediates vitamin K2-activated transcription of extracellular matrix-related genes and collagen accumulation in osteoblastic cells. Ichikawa, T., Horie-Inoue, K., Ikeda, K., Blumberg, B., Inoue, S. J. Biol. Chem. (2006) [Pubmed]
  11. Electron transfer from menaquinol to fumarate. Fumarate reductase anchor polypeptide mutants of Escherichia coli. Westenberg, D.J., Gunsalus, R.P., Ackrell, B.A., Cecchini, G. J. Biol. Chem. (1990) [Pubmed]
  12. Menaquinone (vitamin K2) biosynthesis in Escherichia coli: synthesis of o-succinylbenzoate does not require the decarboxylase activity of the ketoglutarate dehydrogenase complex. Marley, M.G., Meganathan, R., Bentley, R. Biochemistry (1986) [Pubmed]
  13. Interaction of an engineered [3Fe-4S] cluster with a menaquinol binding site of Escherichia coli DMSO reductase. Rothery, R.A., Weiner, J.H. Biochemistry (1996) [Pubmed]
  14. Menaquinone (vitamin K2) biosynthesis: overexpression, purification, and properties of o-succinylbenzoyl-coenzyme A synthetase from Escherichia coli. Kwon, O., Bhattacharyya, D.K., Meganathan, R. J. Bacteriol. (1996) [Pubmed]
  15. The inhibitory effect of vitamin K2 (menatetrenone) on bone resorption may be related to its side chain. Hara, K., Akiyama, Y., Nakamura, T., Murota, S., Morita, I. Bone (1995) [Pubmed]
  16. Vitamin K2 regulation of bone homeostasis is mediated by the steroid and xenobiotic receptor SXR. Tabb, M.M., Sun, A., Zhou, C., Grün, F., Errandi, J., Romero, K., Pham, H., Inoue, S., Mallick, S., Lin, M., Forman, B.M., Blumberg, B. J. Biol. Chem. (2003) [Pubmed]
  17. Ubiquinone at center N is responsible for triphasic reduction of cytochrome b in the cytochrome bc(1) complex. Snyder, C.H., Trumpower, B.L. J. Biol. Chem. (1999) [Pubmed]
  18. Vitamin K2 enhances osteocalcin accumulation in the extracellular matrix of human osteoblasts in vitro. Koshihara, Y., Hoshi, K. J. Bone Miner. Res. (1997) [Pubmed]
  19. Vitamin K2 induces apoptosis of a novel cell line established from a patient with myelodysplastic syndrome in blastic transformation. Nishimaki, J., Miyazawa, K., Yaguchi, M., Katagiri, T., Kawanishi, Y., Toyama, K., Ohyashiki, K., Hashimoto, S., Nakaya, K., Takiguchi, T. Leukemia (1999) [Pubmed]
  20. Apoptosis/differentiation-inducing effects of vitamin K2 on HL-60 cells: dichotomous nature of vitamin K2 in leukemia cells. Miyazawa, K., Yaguchi, M., Funato, K., Gotoh, A., Kawanishi, Y., Nishizawa, Y., Yuo, A., Ohyashiki, K. Leukemia (2001) [Pubmed]
  21. Vitamin K2 and its derivatives induce apoptosis in leukemia cells and enhance the effect of all-trans retinoic acid. Yaguchi, M., Miyazawa, K., Katagiri, T., Nishimaki, J., Kizaki, M., Tohyama, K., Toyama, K. Leukemia (1997) [Pubmed]
  22. Failure to insert the iron-sulfur cluster into the Rieske iron-sulfur protein impairs both center N and center P of the cytochrome bc1 complex. Gutierrez-Cirlos, E.B., Merbitz-Zahradnik, T., Trumpower, B.L. J. Biol. Chem. (2002) [Pubmed]
  23. A NapC/NirT-type cytochrome c (NrfH) is the mediator between the quinone pool and the cytochrome c nitrite reductase of Wolinella succinogenes. Simon, J., Gross, R., Einsle, O., Kroneck, P.M., Kröger, A., Klimmek, O. Mol. Microbiol. (2000) [Pubmed]
  24. Electron transport to periplasmic nitrate reductase (NapA) of Wolinella succinogenes is independent of a NapC protein. Simon, J., Sänger, M., Schuster, S.C., Gross, R. Mol. Microbiol. (2003) [Pubmed]
  25. Effect of cysteine to serine mutations on the properties of the [4Fe-4S] center in Escherichia coli fumarate reductase. Kowal, A.T., Werth, M.T., Manodori, A., Cecchini, G., Schröder, I., Gunsalus, R.P., Johnson, M.K. Biochemistry (1995) [Pubmed]
  26. Roles of NapF, NapG and NapH, subunits of the Escherichia coli periplasmic nitrate reductase, in ubiquinol oxidation. Brondijk, T.H., Fiegen, D., Richardson, D.J., Cole, J.A. Mol. Microbiol. (2002) [Pubmed]
  27. Menaquinone (vitamin K2) biosynthesis: cloning, nucleotide sequence, and expression of the menC gene from Escherichia coli. Sharma, V., Meganathan, R., Hudspeth, M.E. J. Bacteriol. (1993) [Pubmed]
  28. Menaquinone (vitamin K2) biosynthesis: localization and characterization of the menA gene from Escherichia coli. Suvarna, K., Stevenson, D., Meganathan, R., Hudspeth, M.E. J. Bacteriol. (1998) [Pubmed]
  29. Menaquinone (vitamin K2) biosynthesis: localization and characterization of the menE gene from Escherichia coli. Sharma, V., Hudspeth, M.E., Meganathan, R. Gene (1996) [Pubmed]
  30. Vitamin K2 (menatetrenone) effectively prevents fractures and sustains lumbar bone mineral density in osteoporosis. Shiraki, M., Shiraki, Y., Aoki, C., Miura, M. J. Bone Miner. Res. (2000) [Pubmed]
  31. Histochemical evaluation for the biological effect of menatetrenone on metaphyseal trabeculae of ovariectomized rats. Asawa, Y., Amizuka, N., Hara, K., Kobayashi, M., Aita, M., Li, M., Kenmotsu, S., Oda, K., Akiyama, Y., Ozawa, H. Bone (2004) [Pubmed]
  32. Succinate:quinone oxidoreductases--what can we learn from Wolinella succinogenes quinol:fumarate reductase? Lancaster, C.R. FEBS Lett. (2001) [Pubmed]
  33. Effects of vitamin K2 in hemodialysis patients with low serum parathyroid hormone levels. Nakashima, A., Yorioka, N., Doi, S., Masaki, T., Ito, T., Harada, S. Bone (2004) [Pubmed]
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