152044-53-6 Usage
Description
(-)-Epothilone A, also known as Epothilone A, is a secondary metabolite belonging to the epothilone family, which are macrolide compounds with potent antineoplastic properties. It is derived from the myxobacterium Sorangium cellulosum and is characterized by its unique macrocyclic lactone ring with an oxidized double bond, forming the 13R,14S diastereoisomer. (-)-Epothilone A exhibits antitubulin activity, which plays a crucial role in its mechanism of action.
Uses
Used in Anticancer Applications:
(-)-Epothilone A is used as an antineoplastic agent for its ability to inhibit microtubule dynamics, leading to cell cycle arrest at the G2/M transition and inducing apoptosis. (-)-EPOTHILONE A has shown resistance to overexpression of β-tubulin and P-glycoprotein, making it a promising candidate for treating various types of cancer, including human bladder carcinoma.
Used in Drug Development:
(-)-Epothilone A is used as a microtubule inhibitor in the development of novel anticancer drugs. Its mechanism of action involves stabilizing microtubule formation at the taxol binding site, which results in cytotoxicity. This property has led to the investigation of (-)-Epothilone A in clinical trials as a potential antitumor agent, offering a new avenue for cancer treatment.
Used in Pharmaceutical Research:
(-)-Epothilone A is used as a research tool in the pharmaceutical industry for studying the effects of microtubule stabilization on cancer cell growth and the development of drug resistance. Its unique structure and mechanism of action provide valuable insights into the design of new antineoplastic agents and the understanding of cancer cell biology.
Biological Activity
epothilone a (epo a) is a naturally occurring microtubule-stabilizing macrolide that was first isolated from the myxobacterium sorangium cellulosum. the ic50 value of epothilone a in hct-116 cell line is 4.4 nm [1].it has been found that the skov-3 human ovarian cancer cells were susceptible to epothilone a with ic50 value of 20.4 ± 1.4 nm [2]. the antiproliferative capacity of epothilone a in skov-3 cell line (measured as ic50 after 72 h continuous treatment) was six times greater than that of ptx’s. besides, epothilone a induced time coursedependent apoptosis and necrosis [2].
references
[1] regueiro-ren a1, borzilleri rm, zheng x, kim sh, johnson ja, fairchild cr, lee fy, long bh, vite gd. synthesis and biological activity of novel epothilone aziridines. org lett. 2001 aug 23;3(17):2693-6.[2] rogalska a1, marczak a, gajek a, szwed m, ?liwińska a, drzewoski j, jó?wiak z. induction of apoptosis in human ovarian cancer cells by new anticancer compounds, epothilone a and b. toxicol in vitro. 2013 feb;27(1):239-49.
Check Digit Verification of cas no
The CAS Registry Mumber 152044-53-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,2,0,4 and 4 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 152044-53:
(8*1)+(7*5)+(6*2)+(5*0)+(4*4)+(3*4)+(2*5)+(1*3)=96
96 % 10 = 6
So 152044-53-6 is a valid CAS Registry Number.
InChI:InChI=1/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20-,21-,22-,24-/m0/s1
152044-53-6Relevant articles and documents
Total synthesis of epothilone A.
Zhu,Panek
, p. 2575 - 2578 (2000)
[reaction: see text]Epothilones A (1) and B (2) are potent antitumor natural products with a Taxol-like mechanism of action. A total synthesis of epothilone A (1) is reported, which utilized chiral silane-based bond construction methodology to introduce t
Epothilones C, E and F
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Page 8, (2008/06/13)
Epothilone derivatives are obtained by: (1) cultivation of Sorangium cellulosum DSM 6773 in the presence of an absorption resin; (2) separation of the resin and culture followed by washing with aqueous methanol; (3) eluting the washed resin with methanol and reducing the extract; (4) partitioning the extract between methanol and hexane; (5) reducing the methanolic phase and fractionating it on a Sephadex column, and (6) isolation of the epothilones by chromatography using a methanol/water mixture. Epothilone A is followed by epothilone B, and two further fractions.
Total synthesis of epothilone A through stereospecific epoxidation of the p-methoxybenzyl ether of epothilone C
Liu, Zhi-Yu,Chen, Ze-G,Yu, Cheng-Zhi,Wang, Rui-Fang,Zhang, Ru-Zhou,Huang, Chu-Sheng,Yan, Zheng,Cao, De-Rong,Sun, Jian-Bo,Li, Gang
, p. 3747 - 3756 (2007/10/03)
The total synthesis of epothilone A is described by the coupling four segments 4 - 7a. Three of the segments, 4, 5 and 7a, have only one chiral center; all other chiral centers were introduced by simple asymmetric catalytic reactions. The key steps are the ring opening of epoxide 5 with acetylide 8 for the construction of the C12-C13 cis double bond and a practical hydrolytic kinetic resolution (HKR) developed by Jacobsen group for the introduction the chiral center at C3. Especially, the stereospecific epoxidation of 3-O-PMB epothilone C 3b through long-range effect of 3-O-PMB protecting group gave high yields of the C12 - C13 α-epoxide for the synthesis of target molecule.
Synthesis of epothilones, intermediates thereto, analogues and uses thereof
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Page column 37, (2010/01/31)
The present invention provides convergent processes for preparing epothilone A and B, desoxyepothilones A and B, and analogues thereof. Also provided are analogues related to epothilone A and B and intermediates useful for preparing same. The present invention further provides novel compositions based on analogues of the epothilones and methods for the treatment of cancer and cancer which has developed a multidrug-resistant phenotype.
