58053-83-1 Usage
Description
17β-hydroxy Wortmannin is an analog of wortmannin, a natural product derived from the fungus Penicillium wortmannin. It is characterized by its ability to irreversibly bind to phosphoinositide 3-kinase (PI3K), a key enzyme involved in cellular signaling pathways. 17β-hydroxy Wortmannin has demonstrated potent inhibitory effects on various cellular processes, including the respiratory burst in neutrophils, PI3K and mTOR inhibition, and the growth of certain cancer cells.
Uses
Used in Pharmaceutical Industry:
17β-hydroxy Wortmannin is used as a research tool for studying the role of PI3K in various cellular processes, including signal transduction, cell growth, and survival. Its ability to inhibit PI3K and mTOR makes it a valuable compound for investigating the underlying mechanisms of these pathways and their potential as therapeutic targets.
Used in Cancer Research and Treatment:
17β-hydroxy Wortmannin is used as an inhibitor of PI3K and mTOR for the study of their roles in cancer cell growth and proliferation. Its potent inhibition of these enzymes has made it a promising candidate for the development of targeted cancer therapies, particularly for prostate cancer. 17β-hydroxy Wortmannin has demonstrated the ability to prevent the growth of LNCap prostate cancer cells, with an IC50 value of 1.46 μM.
Used in Drug Design and Modification:
The 17-hydroxyl group present in 17β-hydroxy Wortmannin has been utilized for further chemical modifications, such as pegylation and conjugation with rapamycin. These modifications aim to improve the compound's pharmacokinetic properties, solubility, and overall efficacy as a therapeutic agent. By enhancing the properties of 17β-hydroxy Wortmannin, researchers can develop more effective drugs for the treatment of various diseases, including cancer.
Check Digit Verification of cas no
The CAS Registry Mumber 58053-83-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,0,5 and 3 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 58053-83:
(7*5)+(6*8)+(5*0)+(4*5)+(3*3)+(2*8)+(1*3)=131
131 % 10 = 1
So 58053-83-1 is a valid CAS Registry Number.
58053-83-1Relevant articles and documents
Enantioselective Total Synthesis of (+)-Wortmannin
Guo, Yinliang,Quan, Tianfei,Lu, Yandong,Luo, Tuoping
supporting information, p. 6815 - 6818 (2017/05/31)
A concise and enantioselective total synthesis of the potent PI3K inhibitor (+)-wortmannin is described. A Pd-catalyzed cascade reaction was first developed to connect a synthon derived from Hajos-Parrish ketone to a furan moiety. The subsequent Friedel-Crafts alkylation of the β-position of a furan ring to an epoxide was optimized to establish the C10 quaternary center. (+)-Wortmannin was eventually accomplished by transformations following a late-stage oxidation of the furan allylic position. Kinome profiling and in vitro enzymatic assays were performed on 17-β-hydroxy-wortmannin and an epoxide analogue.
Pegylated wortmannin and 17-hydroxywortmannin conjugates as phosphoinositide 3-kinase inhibitors active in human tumor xenograft models
Zhu, Tianmin,Gu, Jianxin,Yu, Ker,Lucas, Judy,Cai, Ping,Tsao, Russ,Gong, Yumin,Li, Fangbiao,Chaudhary, Inder,Desai, Parimal,Ruppen, Mark,Fawzi, Mahdi,Gibbons, James,Ayral-Kaloustian, Semiramis,Skotnicki, Jerauld,Mansour, Tarek,Zask, Arie
, p. 1373 - 1378 (2007/10/03)
Phosphoinositide 3-kinase (PI3K) is an important target for cancer chemotherapy due to the deregulation of its signaling pathway in a wide spectrum of human tumors. Wortmannin and its analogues are potent PI3K inhibitors whose therapeutic use has been impeded by inherent defects such as instability and toxicity. Pegylation of wortmannin and 17-hydroxywortmannin gives rise to conjugates with improved properties, including a higher therapeutic index. Pegylated 17-hydroxywortmannin (8, PWT-458) has been selected for further development.
The first chemical synthesis of wortmannin by starting from hydrocortisone
Sato, Seiji,Nakada, Masahisa,Shibasaki, Masakatsu
, p. 6141 - 6144 (2007/10/03)
The first chemical synthesis of wortmannin, a potent and specific inhibitor of PI 3-kinases, was achieved by starting from commercially available and optically pure hydrocortisone.
