KS 502
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03606 |
| CAS | 120634-85-7 |
| Molecular Weight | 648.74 |
| Molecular Formula | C34H48O12 |
| Purity | >98% |
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Description
It is produced by the strain of Sporothrix sp. KAC-1989. KS 502 inhibited Ca2+ and calmodulin dependent cyclic-nucleotide phosphodiesterase with an IC50 of 4.4 μmol/L.
Specification
| Synonyms | Benzoic acid, 2-(beta-D-galactofuranosyloxy)-6-heptyl-4-hydroxy-, 4-carboxy-3-heptyl-5-hydroxyphenyl ester |
| IUPAC Name | 4-[2-[(2S,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-6-heptyl-4-hydroxybenzoyl]oxy-2-heptyl-6-hydroxybenzoic acid |
| Canonical SMILES | CCCCCCCC1=C(C(=CC(=C1)O)OC2C(C(C(O2)C(CO)O)O)O)C(=O)OC3=CC(=C(C(=C3)O)C(=O)O)CCCCCCC |
| InChI | InChI=1S/C34H48O12/c1-3-5-7-9-11-13-20-15-22(36)17-26(45-34-30(40)29(39)31(46-34)25(38)19-35)28(20)33(43)44-23-16-21(14-12-10-8-6-4-2)27(32(41)42)24(37)18-23/h15-18,25,29-31,34-40H,3-14,19H2,1-2H3,(H,41,42)/t25-,29-,30-,31+,34-/m1/s1 |
| InChI Key | DXFBFWMLNIWYDA-UKRXHORTSA-N |
Properties
| Appearance | Colorless Powder |
| Boiling Point | 893.3°C at 760 mmHg |
| Melting Point | 119-120°C |
| Density | 1.304 g/cm3 |
Reference Reading
1. 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.
2. KS-501 and KS-502, new inhibitors of Ca2+ and calmodulin-dependent cyclic-nucleotide phosphodiesterase from Sporothrix sp
S Nakanishi, K Ando, I Kawamoto, H Kase J Antibiot (Tokyo). 1989 Jul;42(7):1049-55. doi: 10.7164/antibiotics.42.1049.
New inhibitors of Ca2+ and calmodulin-dependent cyclic-nucleotide phosphodiesterase, KS-501 and KS-502 were isolated from a fungus, Sporothrix sp. KAC-1985. Inhibitory concentration causing 50% inhibition (IC50) values of KS-501 and KS-502 for bovine brain enzyme were 1.8 and 4.3 microM, respectively. The compounds exhibited no or weak inhibition for calmodulin-independent cyclic-nucleotide phosphodiesterases and protein kinase C.
3. 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.
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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 ╳
