329689-23-8 Usage
Description
Monastrol is a small molecule that specifically inhibits the mitotic kinesin Eg5, leading to the formation of monopolar spindles and cell cycle arrest in mitosis. This unique mechanism of action makes it a promising candidate for the development of anticancer therapies.
Uses
Used in Anticancer Applications:
Monastrol is used as an anticancer agent, particularly against MCF-7 tumor cells. Its ability to inhibit the mitotic kinesin Eg5 results in the formation of monopolar spindles, which prevents proper cell division and ultimately leads to cell death. This selective targeting of cancer cells makes Monastrol a potential therapeutic option for various cancer types.
Used in Drug Development:
Monastrol is used as a starting point for the development of new drugs targeting the mitotic kinesin Eg5. Its unique mechanism of action provides a foundation for the design of more potent and selective inhibitors, which could lead to improved cancer treatments with fewer side effects.
Used in Cancer Research:
Monastrol is used as a research tool to study the role of mitotic kinesins in cell division and the development of cancer. By understanding the molecular mechanisms underlying the effects of Monastrol, researchers can gain valuable insights into the regulation of the cell cycle and identify potential targets for cancer therapy.
Used in Drug Screening:
Monastrol is used in high-throughput screening assays to identify novel compounds with similar or improved inhibitory activity against mitotic kinesin Eg5. This can help in the discovery of new anticancer agents with potential clinical applications.
Biological Activity
monastrol is a cell-permeable small molecule inhibitor of the mitotic kinesin, eg5. like other kinesins, eg5 can drive the movement of microtubules in vitro.
in vitro
previous study found that monastrol did not inhibit progression through s and g2 phases of the cell cycle or centrosome duplication. the mitotic arrest due to monastrol was also reversible rapidly. chromosomes in monastrol-treated cells frequently had both sister kinetochores attached to microtubules extending to the center of the monoaster. monastrol also inhibited bipolar spindle formation in xenopus egg extracts, however, monastrol did not prevent the targeting of eg5 to the monoastral spindles that form [1].
in vivo
previous study investigated the rat pk and tk of lasom 65, a monastrol derivative. results showed that lasom 65 had good bioavailability and linear pk after oral doses. lasom 65 distributed consistently in lung and fatty tissues. other investigated tissues presented smaller penetration ratios. adverse symptoms were observed only after iv administration, and regressed 3 h after dosing. no statistical differences were found for serum analysis, body weight and relative organ weight, indicating no acute toxicological effects. [2].
IC 50
14 μm
references
[1] kapoor tm,mayer tu,coughlin ml,mitchison tj. probing spindle assembly mechanisms with monastrol, a small molecule inhibitor of the mitotic kinesin, eg5. j cell biol.2000 sep 4;150(5):975-88.[2] torres bg,ucha fde t,pigatto mc,azeredo fj,haas se,dallegrave e,canto rf,eifler-lima vl,dalla costa t. pre-clinical pharmacokinetics and acute toxicological evaluation of a monastrol derivative anticancer candidate lasom 65 in rats. xenobiotica.2014 mar;44(3):254-63.
Check Digit Verification of cas no
The CAS Registry Mumber 329689-23-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,2,9,6,8 and 9 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 329689-23:
(8*3)+(7*2)+(6*9)+(5*6)+(4*8)+(3*9)+(2*2)+(1*3)=188
188 % 10 = 8
So 329689-23-8 is a valid CAS Registry Number.
InChI:InChI=1/C14H16N2O3S/c1-3-19-13(18)11-8(2)15-14(20)16-12(11)9-5-4-6-10(17)7-9/h4-7,12,17H,3H2,1-2H3,(H2,15,16,20)
329689-23-8Relevant articles and documents
Application of design of experiments (Doe) approach for the optimization of phase-transfer catalyzed biginelli dihydropyrimidinone (dhpm) synthesis
Durai Ananda Kumar, T.,Satyanarayana, K.,Subrahmanyam, C. V. S.,Swathi, N.
, p. 520 - 531 (2021/07/25)
The conventional Biginelli synthesis is more cumbersome and produces lower yields. Several improved methods are reported in the literature to replace the Biginelli catalyst. The design of biocompatible organic transformation is a major concern and a versa
A novel H2S releasing-monastrol hybrid (MADTOH) inhibits L-type calcium channels
Braga, Taniris Cafiero,De Jesus, Itamar Couto Guedes,Soares, Kathleen Viveiros,Guatimosim, Silvia,Da Silva Neto, Leonardo,Da-Silva, Cristiane Jovelina,Modolo, Luzia Valentina,Menezes Filho, José Evaldo Rodrigues,Rhana, Paula,Cruz, Jader Santos,De Fátima, ?ngelo
, p. 671 - 678 (2021/01/25)
A new alleged monastrol-H2S releasing hybrid, named MADTOH, was designed based on the structure of monastrol (M) and 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione (ADTOH) and synthesized in 7.8% overall yield. MADTOH was shown to be an H2S donor under physiological conditions. In addition, the hybrid causes a decrease in global calcium transient in cardiomyocytes similar to nifedipine (NIFE), taken as a positive control. Whole-cell voltage-clamp showed that MADTOH decreases L-type Ca2+ current in isolated ventricular cardiomyocytes.
Concentrated solar radiation as a renewable heat source for a preparative-scale and solvent-free Biginelli reaction
Gadkari, Yatin U.,Hatvate, Navnath T.,Takale, Balaram S.,Telvekar, Vikas N.
supporting information, p. 8167 - 8170 (2020/06/09)
A well-known Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones was performed in an environmentally responsible manner. Large numbers of substrates were screened, and found to give excellent yields of the desired products. In
