YUA001
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01565 |
| CAS | |
| Molecular Weight | 221.29 |
| Molecular Formula | C13H19NO2 |
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Description
YUA001 is an aldose reductase inhibitor produced from alkalophilic Corynebacterium sp. YUA25. It has no antimicrobial activity.
Specification
| Synonyms | YUA-001 |
| IUPAC Name | N-[2-(4-hydroxyphenyl)ethyl]-2-methylbutanamide |
| Canonical SMILES | CCC(C)C(=O)NCCC1=CC=C(C=C1)O |
| InChI | InChI=1S/C13H19NO2/c1-3-10(2)13(16)14-9-8-11-4-6-12(15)7-5-11/h4-7,10,15H,3,8-9H2,1-2H3,(H,14,16) |
| InChI Key | GHWNXVWVLOGWPT-UHFFFAOYSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 103°C |
Reference Reading
1. Rational design of an indolebutanoic acid derivative as a novel aldose reductase inhibitor based on docking and 3D QSAR studies of phenethylamine derivatives
Won Suck Sun, Yoon Sun Park, Jakyung Yoo, Ki Duk Park, Sung Han Kim, Jung-Han Kim, Hyun-Ju Park J Med Chem. 2003 Dec 18;46(26):5619-27. doi: 10.1021/jm0205346.
A series of 45 phenethylamine derivatives were synthesized and evaluated for their inhibitory activity against pig kidney aldose reductase (ALR2, EC 1.1.1.21). Their IC(50) values ranged from 400 microM to 24 microM. The binding modes of compounds at the active site of ALR2 were examined using flexible docking. The results indicated that phenethylamine derivatives nicely fit into the active pocket of ALR2 by forming various hydrogen bonding and hydrophobic interactions. 3D-QSAR analysis was also conducted using FlexX-docked alignment of the compounds. The best prediction was obtained by CoMSIA combined with hydrophobic and hydrogen bond donor/acceptor field (q(2) = 0.557, r(2) = 0.934). A new derivative, 4-oxo-4-(4-hydroxyindole)butanoic acid, was designed, taking into account the CoMSIA field and the binding mode derived by FlexX docking. This rationally designed compound exhibits an ALR2 inhibition with an IC(50) value of 7.4 microM, which compares favorably to that of a well-known ALR2 inhibitor, tolrestat (IC(50) = 16 microM) and represents a potency approximately 240-fold higher than that of an original phenethylamine lead compound, YUA001.
2. YUA001, a novel aldose reductase inhibitor isolated from alkalophilic Corynebacterium sp. YUA25. II. Chemical modification and biological activity
W S Sun, H S Lee, J M Park, S H Kim, J H Yu, J H Kim J Antibiot (Tokyo). 2001 Oct;54(10):827-30. doi: 10.7164/antibiotics.54.827.
A series of novel N-substituted tyramine (2-p-hydroxyphenylethylamine) derivatives (1 to approximately 11) were synthesized and evaluated for their inhibitory activity against pig kidney aldose reductase (EC 1, 1, 1, 21). Of these compounds, N-2-p-hydroxyphenylethyl maleamic acid (10) exhibits the strongest aldose reductase inhibitory activity, which is 22 times more potent than that of YUA001.
3. Cells adapted to the proteasome inhibitor 4-hydroxy- 5-iodo-3-nitrophenylacetyl-Leu-Leu-leucinal-vinyl sulfone require enzymatically active proteasomes for continued survival
M F Princiotta, U Schubert, W Chen, J R Bennink, J Myung, C M Crews, J W Yewdell Proc Natl Acad Sci U S A. 2001 Jan 16;98(2):513-8. doi: 10.1073/pnas.98.2.513. Epub 2001 Jan 9.
The proteasome is the primary protease used by cells for degrading proteins and generating peptide ligands for class I molecules of the major histocompatibility complex. Based on the properties of cells adapted to grow in the presence of the proteasome inhibitor 4-hydroxy-5-iodo-3-nitrophenylacetyl-Leu-Leu-leucinal-vinyl sulfone (NLVS), it was proposed that proteasomes can be replaced by alternative proteolytic systems, particularly a large proteolytic complex with a tripeptidyl peptidase II activity. Here we show that NLVS-adapted cells retain sensitivity to a number of highly specific proteasome inhibitors with regard to antigenic peptide generation, accumulation of polyubiquitinated proteins, degradation of p53, and cell viability. In addition, we show that in the same assays (with a single minor exception), NLVS-adapted cells are about as sensitive as nonselected cells to Ala-Ala-Phe-chloromethylketone, a specific inhibitor of tripeptidyl peptidase II activity. Based on these findings, we conclude that proteasomes still have essential proteolytic functions in adapted cells that are not replaced by Ala-Ala-Phe-chloromethylketone-sensitive proteases.
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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 ╳
