UCH9
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| Category | Antibiotics |
| Catalog number | BBF-01590 |
| CAS | |
| Molecular Weight | 1127.2 |
| Molecular Formula | C55H82O24 |
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Description
UCH9 is an antitumor antibiotic produced Streptomyces. II. It exhibits bacteriophage and gram-positive bacteria activity.
Specification
| Synonyms | UCH-9; UCH 9 |
| IUPAC Name | (2S,3S)-7-butan-2-yl-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-6-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-2-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-methoxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8,9-dihydroxy-3,4-dihydro-2H-anthracen-1-one |
| Canonical SMILES | CCC(C)C1=C(C2=C(C3=C(CC(C(C3=O)OC4CC(C(C(O4)C)O)OC5CC(C(C(O5)C)O)OC6CC(C(C(O6)C)OC)OC7CC(C(C(O7)C)O)O)C(C(=O)C(C(C)O)O)OC)C=C2C=C1OC8CC(C(C(O8)C)O)O)O)O |
| InChI | InChI=1S/C55H82O24/c1-11-20(2)41-32(75-36-15-30(57)45(60)22(4)70-36)14-28-12-27-13-29(54(69-10)52(67)44(59)21(3)56)55(51(66)43(27)50(65)42(28)49(41)64)79-40-18-34(48(63)25(7)73-40)76-38-17-33(47(62)24(6)72-38)77-39-19-35(53(68-9)26(8)74-39)78-37-16-31(58)46(61)23(5)71-37/h12,14,20-26,29-31,33-40,44-48,53-65H,11,13,15-19H2,1-10H3/t20?,21-,22-,23-,24-,25-,26-,29+,30-,31-,33-,34-,35-,36-,37+,38+,39+,40+,44+,45-,46-,47+,48-,53-,54+,55+/m1/s1 |
| InChI Key | MTNZDABNNNQWLZ-WUIFBNNWSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
Reference Reading
1. UCH9, a new antitumor antibiotic produced by Streptomyces. II. Structure elucidation of UCH9 by mass and NMR spectroscopy
R Katahira, Y Uosaki, H Ogawa, Y Yamashita, H Nakano, M Yoshida J Antibiot (Tokyo). 1998 Mar;51(3):267-74. doi: 10.7164/antibiotics.51.267.
The structure of UCH9, which is a novel antitumor agent, was determined by spectroscopic methods. UCH9 consists of an aglycone and five 2,6-dideoxy sugars (three D-olivoses, one 4-O-methyl-D-olivose and one D-oliose). Four of the five sugars are sequentially connected through a beta 1-->3 linkage (olivose-1-->3-4-O-methyl-olivose-1-->3-oliose-1-->3-+ ++olivose). On the basis of the results of spectroscopic analysis, it was found that UCH9 belongs to the aureolic acid family of antibiotics. The structure of UCH9 is unique in that mono- and tetrasaccharide moieties, and a long hydrophobic side chain (sec-butyl group) are attached to the aglycone, while di- and trisaccharide moieties and a methyl or a hydrogen are attached in the case of the known aureolic acid analogs. It is known that aureolic acid analogs from a dimer in the presence of Mg2+. NMR, FAB-MS and atomic absorption analysis revealed that UCH9 isolated from Streptomyces also forms a dimer, containing one equivalent molar Mg2+.
2. Evaluation of the anti-inflammatory and analgesic activity of Me-UCH9, a dual cyclooxygenase-2/5-lipoxygenase inhibitor
A Araico, M C Terencio, M J Alcaraz, J N Domínguez, C León, M L Ferrándiz Life Sci. 2007 May 16;80(23):2108-2117. doi: 10.1016/j.lfs.2007.03.017. Epub 2007 Apr 4.
Recently, we reported the dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LO) activity by some phenylsulphonyl urenyl chalcone derivatives. 2,4-dichloro-4'N[N'(4''methylphenylsulphonyl)urenyl] chalcone (Me-UCH9), was selected in the present study to determine its potential anti-inflammatory and analgesic effect after oral administration in several animal models related to the activation of COX-2 and 5-LO pathways. In the zymosan stimulated mouse air pouch model, Me-UCH9, reduced in a dose-dependent manner leukotriene B(4) (LTB(4)) levels in pouch exudates obtained at 4 h, as well as prostaglandin E(2) (PGE(2)) generated through COX-2 activation at 24 h. Tumor necrosis factor alpha (TNF-alpha) and myeloperoxidase activity were also strongly inhibited in this model. Me-UCH9 significantly reduced granuloma size and vascular index determined in the murine air pouch granuloma model of angiogenesis. In the carrageenan-induced paw edema, this compound inhibited inflammatory response and pain, as well as PGE(2) and LTB(4) content in paw edematous fluid. Analgesic properties were corroborated in the murine phenyl-p-benzoquinone-induced writhing test. Finally, Me-UCH9 exerted anti-inflammatory effects in the chronic model of rat adjuvant-induced arthritis, both inhibiting paw swelling and reducing PGE(2) content. Our findings confirm that Me-UCH9 can modulate inflammatory and nociceptive responses in relation to the dual inhibition of COX-2 and 5-LO activities presented by this compound.
3. UCH9, a new antitumor antibiotic produced by Streptomyces: I. Producing organism, fermentation, isolation and biological activities
H Ogawa, Y Yamashita, R Katahira, S Chiba, T Iwasaki, T Ashizawa, H Nakano J Antibiot (Tokyo). 1998 Mar;51(3):261-6. doi: 10.7164/antibiotics.51.261.
We developed a microbial prescreen using Bacillus stearothermophilus NUB3620 and bacteriophage TP-68 to detect potential antitumor compounds acting on DNA or topoisomerases. During the course of screening microbial cultures for their antibacteriophage activities, we found that Streptomyces sp. isolated from a soil sample collected in Iwakuni city, Yamaguchi prefecture, Japan, produced a new antitumor antibiotic, UCH9. UCH9 was isolated from culture broth by a combination of EtOAc extraction and column chromatography. UCH9 has a new structure related to the antitumor antibiotic chromomycins. It exhibited antimicrobial activity against Gram-positive organisms. UCH9 also showed cytotoxic activity against HeLa S3 cells with an IC50 value of 13 nM and exhibited antitumor activity in vivo against mouse leukemia P388.
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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 ╳
