KS-501
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03605 |
| CAS | 120634-86-8 |
| Molecular Weight | 604.73 |
| Molecular Formula | C33H48O10 |
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Description
It is produced by the strain of Sporothrix sp. KAC-1989. KS-501 inhibited Ca2+ and calmodulin dependent cyclic-nucleotide phosphodiesterase with an IC50 of 1.8 μmol/L.
Specification
| Synonyms | KS 501; 3-Heptyl-5-hydroxyphenyl 2-heptyl-6-(hexofuranosyloxy)-4-hydroxybenzoate |
| IUPAC Name | (3-heptyl-5-hydroxyphenyl) 2-[(2S,3R,4R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-6-heptyl-4-hydroxybenzoate |
| Canonical SMILES | CCCCCCCC1=CC(=CC(=C1)OC(=O)C2=C(C=C(C=C2OC3C(C(C(O3)C(CO)O)O)O)O)CCCCCCC)O |
| InChI | InChI=1S/C33H48O10/c1-3-5-7-9-11-13-21-15-23(35)18-25(16-21)41-32(40)28-22(14-12-10-8-6-4-2)17-24(36)19-27(28)42-33-30(39)29(38)31(43-33)26(37)20-34/h15-19,26,29-31,33-39H,3-14,20H2,1-2H3/t26-,29-,30-,31?,33-/m1/s1 |
| InChI Key | MPAXORHHSMKMHV-ZUSOEIMYSA-N |
Properties
| Appearance | Colorless Powder |
| Boiling Point | 821.7°C at 760 mmHg |
| Melting Point | 149-152°C |
| Density | 1.247 g/cm3 |
Reference Reading
1. Structures of KS-501 and KS-502, the new inhibitors of Ca2+ and calmodulin-dependent cyclic nucleotide phosphodiesterase
T Yasuzawa, Y Saitoh, H Sano J Antibiot (Tokyo). 1990 Apr;43(4):336-43. doi: 10.7164/antibiotics.43.336.
The structures of KS-501 and KS-502, new inhibitors of Ca2+ and calmodulin-dependent cyclic nucleotide phosphodiesterase, were determined to be 2-(beta-D-galactofuranosyloxy)-6-heptyl-4-hydroxybenzoic acid 3-heptyl-5-hydroxyphenyl ester and 2-(beta-D-galactofuranosyloxy)6-heptyl-4-hydroxybenzoic acid 4-carboxy-3-heptyl-5-hydroxyphenyl ester, respectively, on the basis of chemical and physico-chemical evidences.
2. Effects of KS-501, KS-502 and their enantiomers on calmodulin-sensitive enzyme activity and cellular proliferation
W N Hait, J Gesmonde, E Cheng Biochem Pharmacol. 1995 Jun 29;50(1):69-74. doi: 10.1016/0006-2952(95)00105-9.
Calmodulin plays an important role in cellular proliferation as part of a signal transduction pathway activated by phospholipase C. Drugs that block the ability of calmodulin to bind to and activate its target enzymes inhibit the growth of a wide variety of malignant cells. To identify more potent and selective inhibitors of this potential target for new drug development, we studied two recently synthesized compounds, KS-501 and KS-502, for their activity against calmodulin-sensitive enzymes and for their ability to block the growth of parental and multidrug-resistant leukemic cells. KS-501 and KS-502 inhibited the activation of a calmodulin-sensitive cyclic nucleotide phosphodiesterase. The mechanism of enzyme inhibition was through interfering with calmodulin activation rather than through a direct effect on the enzyme. KS-501 was more potent than KS-502 and was studied in greater detail. This compound inhibited the activation of calmodulin kinase I and II, but had less effect against cyclic adenosine 3',5'-monophosphate (cyclic AMP)-sensitive kinase. KS-501 was also more effective than KS-502 in inhibiting the growth of sensitive L1210 leukemic lymphocytes. Both compounds were less effective inhibitors of multidrug-resistant L1210 leukemia than of the parental line. These studies identify a new class of calmodulin inhibitor, with selectivity for calmodulin-dependent kinases over cyclic AMP-dependent protein kinase. Since the total synthesis of the KS-compounds has been accomplished, it should now be possible to develop derivatives with greater activity and selectivity.
3. Phenolic glycosides from the filamentous fungus Acremonium sp. BCC 14080
Taridaporn Bunyapaiboonsri, Seangaroon Yoiprommarat, Artit Khonsanit, Somjit Komwijit J Nat Prod. 2008 May;71(5):891-4. doi: 10.1021/np070689m. Epub 2008 Mar 26.
New phenolic mono- and digalactopyranosides (1 and 2), their aglycone KS-501a (3), and a new phenolic 4-O-methylglucopyranoside (4) were isolated from the filamentous fungus Acremonium sp. BCC 14080. Structures of these compounds were elucidated by extensive MS and NMR spectroscopic analyses. Compound 1 displayed anti-HSV-1 activity with an IC(50) value of 7.2 microM. Compound 3 exhibited activity against Plasmodium falciparum K1 with an IC(50) value of 9.9 microM.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
