87414-49-1 Usage
Description
Butyrolactone I is a member of a family of three butyrolactones derived from Aspergillus fumigatus, first identified in 1983. It is recognized for its antitumor properties, which are attributed to its ability to inhibit the cell cycle at the G1/S and G2/M transitions. As a selective inhibitor of cyclin-dependent kinases CDK1/cyclin B, CDK2, and CDK5, Butyrolactone I serves as a significant bioprobe for elucidating the cellular functions of CDKs.
Uses
Used in Pharmaceutical Industry:
Butyrolactone I is used as an antitumor agent for its capacity to impede the progression of the cell cycle, specifically at the G1/S and G2/M transitions. This property makes it a valuable compound in the development of cancer therapeutics.
Used in Biochemical Research:
As a selective inhibitor of cyclin-dependent kinases CDK1/cyclin B, CDK2, and CDK5, Butyrolactone I is utilized as a crucial bioprobe in biochemical research. It aids scientists in studying the roles and mechanisms of CDKs within cellular processes, which is instrumental for understanding various diseases and conditions related to cell cycle regulation.
Enzyme inhibitor
This natural product (FW = 424.45 g/mol), first identified in species of Aspergillus and named systematically as 2,5-dihydro-4-hydroxy 2-([4- hydroxy-3-(3-methyl-2-butenyl)phenyl]methyl)-3-(4-hydroxyphenyl)-5-oxo- 2-furancarboxylic acid methyl ester, competes with ATP in cyclindependent kinase reactions. The IC50 values for these kinases are typically 0.6-1.5 μM. Butyrolactone I also inhibits cell proliferation by the inhibiting pRb phosphorylation in IMR32 cells, causing both G1 and G2 arrest and stimulating apoptosis. Target(s): cyclin-dependent kinases 1 and 2; cdk5; protein kinase C; protein kinase A; MAP kinase; casein kinase II; [tau protein] kinase.
Check Digit Verification of cas no
The CAS Registry Mumber 87414-49-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,7,4,1 and 4 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 87414-49:
(7*8)+(6*7)+(5*4)+(4*1)+(3*4)+(2*4)+(1*9)=151
151 % 10 = 1
So 87414-49-1 is a valid CAS Registry Number.
InChI:InChI=1/C24H24O7/c1-14(2)4-6-17-12-15(5-11-19(17)26)13-30-23(29)24(3)20(21(27)22(28)31-24)16-7-9-18(25)10-8-16/h4-5,7-12,25-27H,6,13H2,1-3H3/t24-/m1/s1
87414-49-1Relevant articles and documents
Molecular insights into the enzyme promiscuity of an aromatic prenyltransferase
Chen, Ridao,Gao, Bingquan,Liu, Xiao,Ruan, Feiying,Zhang, Yong,Lou, Jizhong,Feng, Keping,Wunsch, Carsten,Li, Shu-Ming,Dai, Jungui,Sun, Fei
, p. 226 - 234 (2017/01/28)
Aromatic prenyltransferases (aPTases) transfer prenyl moieties from isoprenoid donors to various aromatic acceptors, some of which have the rare property of extreme enzymatic promiscuity toward both a variety of prenyl donors and a large diversity of acceptors. In this study, we discovered a new aPTase, AtaPT, from Aspergillus terreus that exhibits unprecedented promiscuity toward diverse aromatic acceptors and prenyl donors and also yields products with a range of prenylation patterns. Systematic crystallographic studies revealed various discrete conformations for ligand binding with donor-dependent acceptor specificity and multiple binding sites within a spacious hydrophobic substrate-binding pocket. Further structure-guided mutagenesis of active sites at the substrate-binding pocket is responsible for altering the specificity and promiscuity toward substrates and the diversity of product prenylations. Our study reveals the molecular mechanism underlying the promiscuity of AtaPT and suggests an efficient protein engineering strategy to generate new prenylated derivatives in drug discovery applications.
