CKD-711
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02786 |
| CAS | |
| Molecular Weight | 677.60 |
| Molecular Formula | C25H43NO20 |
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Description
It is produced by the strain of Streptomyces sp. CK-4416. CKD-711 strongly inhibited mammalian α-glucosidase activity, but weakly inhibited mammalian α-amylase from microorganism and mammal, which was similar to acarbose in vivo and in vitro.
Specification
| Synonyms | 4-Deoxy-4-{[(1R,2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-2-yl]amino}-α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)-D-glucopyranose |
| IUPAC Name | (1S,2S,3R,4S,5R,6R)-5-[[(2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]amino]-1-(hydroxymethyl)-7-oxabicyclo[4.1.0]heptane-2,3,4-triol |
| Canonical SMILES | C(C1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)O)CO)CO)O)O)NC4C(C(C(C5(C4O5)CO)O)O)O)O |
| InChI | InChI=1S/C25H43NO20/c27-1-5-8(26-9-11(32)14(35)20(39)25(4-30)21(9)46-25)10(31)16(37)23(42-5)45-19-7(3-29)43-24(17(38)13(19)34)44-18-6(2-28)41-22(40)15(36)12(18)33/h5-24,26-40H,1-4H2/t5-,6-,7-,8-,9-,10+,11+,12-,13-,14-,15-,16-,17-,18-,19-,20+,21-,22?,23-,24-,25+/m1/s1 |
| InChI Key | PHKYGBHARUTZOY-KTVVNDHVSA-N |
Properties
| Boiling Point | 1041.5±65.0°C at 760 mmHg |
| Density | 1.9±0.1 g/cm3 |
Reference Reading
1. Novel alpha-glucosidase inhibitors, CKD-711 and CKD-711a produced by Streptomyces sp. CK-4416. II. Biological properties
Young-In Kwon, Hyeog-Jin Son, Kyoung Sik Moon, Joon Kyum Kim, Jong-Gwan Kim, Hyoung-Sik Chun, Soon Kil Ahn, Chung Il Hong J Antibiot (Tokyo). 2002 May;55(5):462-6. doi: 10.7164/antibiotics.55.462.
CKD-711 and CKD-711a are aminooligosaccharide alpha-glucosidase inhibitors discovered during the bioactive material screening for antibacterial agent. Their inhibitory activities were studied and compared with those of acarbose in vitro and in vivo with animals. In in vitro study, CKD-711 showed similar effects to acarbose on porcine intestinal maltase and sucrase, IC50s of 2.5 and 0.5 microg/ml, respectively, whereas it had about 2 fold lower alpha-amylase inhibitory activity (IC50, 78.0 microg/ml) than acarbose (IC50, 36 microg/ml). CKD-711a showed less inhibitory activity than CKD-711 against all the enzymes tested. In rat fed on starch and sucrose meals, the dose of CKD-711 which reduced the postprandial blood glucose increment by 50 percent in comparison to control rats (ED50) were 3.07 and 1.15 mg/kg, respectively, and acarbose had ED50s of 1.94 and 1.15 mg/kg, respectively. CKD-711 and CKD-711a also showed antibacterial activity against Comamonas terrigena.
2. Novel alpha-glucosidase inhibitors, CKD-711 and CKD-711a produced by Streptomyces sp. CK-4416. III. Physico-chemical properties and structure elucidation
Hung-Bae Chang, Sun-Ho Kim, Young-In Kwon, Dong-Ho Choung, Won-Kyu Choi, Tae Won Kang, Sungsook Lee, Jong-Gwan Kim, Hyoung-Sik Chun, Soon Kil Ahn, Chung Il Hong, Kyou-Hoon Han J Antibiot (Tokyo). 2002 May;55(5):467-71. doi: 10.7164/antibiotics.55.467.
We have isolated two novel a-glucosidase inhibitors, O-[4-deoxy-4-(2,3-epoxy-3-hydroxymethyl-4,5,6-trihydroxycyclohexane-1-yl-amino)-alpha-D-glucopyranosyl]-(1-->4)-O-alpha-D-glucopyranosyl-(1-->4)-alpha-D-glucopyranose (named CKD-711) and its hexameric analog CKD-711a, from the fermentation broth of Streptomyces sp. CK-4416. HRFAB-MS and NMR analyses reveal that molecular formulae of CKD-711 and CKD-711a are C25H43NO20 and C37H63NO30, respectively with the latter containing two more glucose moieties than the former. Detailed chemical structures of both compounds have been characterized by high-resolution two-dimensional NMR methods.
3. Studies on α-glucosidase inhibitors development: magic molecules for the treatment of carbohydrate mediated diseases
N S H N Moorthy, M J Ramos, P A Fernandes Mini Rev Med Chem. 2012 Jul;12(8):713-20. doi: 10.2174/138955712801264837.
α-Glucosidase (EC 3.2.1.20) enzyme belongs to the glycosidase family enzymes, cleave the glycosidic bond of the oligosaccharides that liberate glucose and its inhibition retards the carbohydrate digestion. In the present review, we have discussed the structural features of different α-glucosidase inhibitors (small molecules) responsible for the inhibitory activities. The reported computational studies including, QSAR, pharmacophore modelling, homology models, docking (with analogs enzymes), etc revealed that the topological, electronic and hydrophobicity properties determine the interactions of those molecules. The aromatic substituents connected with flexible bonds in the molecules have significant effect on the interactions, which may due to the presence of aromatic amino acid residues in the active site. The reported homology modelled and other analogs enzymes (enzymes of other species) also confirmed the existence of aromatic residue (amino acids) especially, histidine, phenylalanine and tyrosine in their active site along with the polar (glutamic and aspartic acids) residues. Multiple sequence alignments of the α-glucosidase enzymes (from different species) described that the abovementioned amino acid residues are present in the active site of all the studied enzymes. Recently, Celgosivir (MIGENIX Inc) is an oral prodrug of the natural product castanospermine used for the treatment of HCV infection by inhibiting α-glucosidase I. BMN-701 is an α-glucosidase inhibitors in the phase I pipeline (BioMarine) for the treatment of Pompe diseases. CKD-711 and CKD-711a are aminooligosaccharide α-glucosidase inhibitors and the in vitro study of CKD-711 showed similar effects to acarbose on porcine intestinal maltase and sucrase (IC50s of 2.5 and 0.5 μg/ml). This review also concluded that many α-glucosidases inhibitors obtained from natural products are used for the treatment of various carbohydrate mediated diseases. The structural analysis of these synthetic and natural derivatives guide for the development of novel semisynthetic/synthetic α-glucosidase inhibitors with free of toxicities.
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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 ╳
