K 259-2

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K 259-2
Category Enzyme inhibitors
Catalog number BBF-03599
CAS 102819-46-5
Molecular Weight 382.36
Molecular Formula C21H18O7

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K-259-2, a new inhibitor of Ca2+ and calmodulin-dependent cyclic nucleotide phosphodiesterase, was isolated from the cultured broth of Micromonospora olivasterospora K-259. IC50 values for the effect of K-259-2 against Ca2+ and calmodulin-stimulated activity of the enzyme preparations from bovine brain and heart were 6.6 and 2.9 microM, respectively.


Synonyms K-259-2; 1,6,8-Trihydroxy-3-[(Z)-2-ethyl-2-butenyl]-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid
IUPAC Name 3-[(Z)-2-ethylbut-2-enyl]-1,6,8-trihydroxy-9,10-dioxoanthracene-2-carboxylic acid
Canonical SMILES CCC(=CC)CC1=CC2=C(C(=C1C(=O)O)O)C(=O)C3=C(C2=O)C=C(C=C3O)O
InChI InChI=1S/C21H18O7/c1-3-9(4-2)5-10-6-12-17(19(25)15(10)21(27)28)20(26)16-13(18(12)24)7-11(22)8-14(16)23/h3,6-8,22-23,25H,4-5H2,1-2H3,(H,27,28)/b9-3-


Appearance Red Crystal
Boiling Point 672.6°C at 760 mmHg
Melting Point 140-145°C
Density 1.475 g/cm3

Reference Reading

1. [Analysis of vitamins and inorganic elements in the water extracts of Radix Changii]
Jian-Wei Chen, Xiang Li, Hou-Min Zhao Zhong Xi Yi Jie He Xue Bao. 2004 Sep;2(5):379-81. doi: 10.3736/jcim20040520.
Objective: To study the material basis of the tonifying effect of Radix Changii by observing its contents of nutrient elements. Methods: The contents of vitamins in Radix Changii and inorganic elements in the water extracts of it were tested by high performance liquid chromatography, fluorescence spectrophotography and scanning electron microanalysis. Results: Radix Changii contains fat-soluble vitamins E and K 259.2 and 64.1 microg/kg respectively, and water-soluble vitamins C, B1 and B2 78.5, 0.6 and 0.7 mg/kg respectively. Its decoction contains abundant potassium and calcium ions. Conclusion: Radix Changii is rich in elements necessary for human body. It has the material basis for tonification.
2. Inhibition by new anthraquinone compounds, K-259-2 and KS-619-1, of calmodulin-dependent cyclic nucleotide phosphodiesterase
Y Matsuda, S Nakanishi, K Nagasawa, H Kase Biochem Pharmacol. 1990 Mar 1;39(5):841-9. doi: 10.1016/0006-2952(90)90198-t.
K-259-2 and KS-619-1, novel anionic anthraquinone metabolites isolated from culture broth of microorganisms, inhibited activation of bovine brain phosphodiesterase induced by calmodulin (CaM), sodium oleate, or limited proteolysis with almost equal potency. The inhibition of calmodulin-activated phosphodiesterase (CaM-PDE) by K-259-2 or KS-619-1 was overcome by a higher concentration of CaM. Direct interaction of K-259-2 and KS-619-1 with CaM was confirmed through use of hydrophobic fluorescent probes. Kinetic analysis revealed that the inhibition of the trypsin-activated phosphodiesterase was competitively inhibited by K-259-2 or KS-619-1 with respect to cAMP. Addition of a lower amount of either phosphatidylserine or sodium oleate to the reaction mixture was efficacious in attenuating the inhibition of the CaM-PDE by W-7, chlorpromazine, trifluoperazine, compound 48/80, or R-24571 but, in contrast, had little or no effect on the inhibition by K-259-2 or KS-619-1. In conclusion, K-259-2 and KS-619-1, unlike so-called CaM antagonists, do not interact with phosphatidylserine or sodium oleate and it appears that these novel anthraquinone compounds inhibit the enzyme not only via CaM antagonism but possibly also by interacting directly with the enzyme.
3. Structure of a novel Ca2+ and calmodulin-dependent cyclic nucleotide phosphodiesterase inhibitor K-259-2
T Yasuzawa, M Yoshida, K Shirahata, H Sano J Antibiot (Tokyo). 1987 Aug;40(8):1101-3. doi: 10.7164/antibiotics.40.1101.
The structure of K-259-2, a potent inhibitor of Ca2+ and calmodulin-dependent cyclic nucleotide phosphodiesterase, was determined to be 3-(2Z-2-ethyl-2-butenyl)-1,6,8-trihydroxy-anthraquinone-2-carboxyl ic acid by chemical conversion and spectral studies.

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