22862-76-6 Usage
Uses
Used in Pharmaceutical Applications:
Anisomycin is used as an antiparasitic agent for its antiprotozoan and antifungal activities. It acts as a protein synthesis inhibitor by blocking translation, which can be useful in treating certain parasitic infections.
Used in Cancer Research:
Anisomycin is used as an antineoplastic agent, inducing apoptosis and sensitizing cells to anoikis. It also acts as a potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase, which can be beneficial in cancer research and treatment.
Used in Signal Transduction Research:
Anisomycin is used as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB, and junD). This makes it a valuable tool in studying signal transduction pathways and their role in various cellular processes.
Used in Immunological Research:
Anisomycin is used to study its immunomodulatory effects on T cells, which can provide insights into the immune system and potential applications in immunological research and therapy.
Biological Activity
Protein synthesis inhibitor (blocks translation). Potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. Acts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD).
Biochem/physiol Actions
Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes. Reported to induce apoptosis in a variety of cells including promyelocytic leukemia cells, Jurkat cells, ventricular myocytes, and colon adenocarcinoma cells. Initiates intracellular signals and immediate early gene induction. Selective signaling agonist. Potent Jun-NH2 terminal kinase (JNK) agonist. Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK). Antiprotozoal agent.
References
1) Hazzalin?et al. (1998),?Anisomycin Selectively Desensitizes Signalling Components Involved in Stress Kinase Activation and fos and jun Induction; Mol. Cell. Bio.,?8?1844
2) Mawji?et al. (2007),?A Chemical Screen Identifies Anisomycin as an Anoikis Sensitizer That Functions by Decreasing FLIP Protein Synthesis; Cancer Res.,?67?8307
Check Digit Verification of cas no
The CAS Registry Mumber 22862-76-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,8,6 and 2 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 22862-76:
(7*2)+(6*2)+(5*8)+(4*6)+(3*2)+(2*7)+(1*6)=116
116 % 10 = 6
So 22862-76-6 is a valid CAS Registry Number.
InChI:InChI=1/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/p+1/t12-,13+,14+/m1/s1
22862-76-6Relevant academic research and scientific papers
Concise synthesis of (-)-anisomycin
Li, Ji,Feng, Yan Hua,Li, Xin Bai,Han, Wei,Liu, Huan Qiu,Shao, Guo Guang
, p. 647 - 649 (2012/08/13)
The antibiotic (-)-anisomycin was synthesized starting from d-tyrosine using Sharpless asymmetric epoxidation as a key reaction followed by formation and hydrolysis of oxazoline set up all chiral center.
Application of Pd(0)-catalyzed intramolecular oxazine formation to the efficient total synthesis of ( - )-anisomycin
Joo, Jae-Eun,Lee, Kee-Young,Pham, Van-Thoai,Tian, Yong-Shou,Ham, Won-Hun
, p. 3627 - 3630 (2008/02/12)
The enantioselective total synthesis of ( - )-anisomycin, a potent antibiotic agent, has been achieved. The key steps are a Pd(0)-catalyzed stereoselective intramolecular oxazine formation from D-tyrosine and pyrrolidine formation by catalytic hydrogenation of the oxazine.
Asymmetric amidation of (2S,3S)-pent-4-ene-1,2,3-triol. Total syntheses of (-)-anisomycin and (+)-polyoxamic acid
Kang, Sung Ho,Choi, Hyeong-Wook
, p. 1521 - 1522 (2007/10/03)
Intramolecular iodoamidation of pentenetriol 2 provides trihydroxy carbamate 8 in 94% de and was elaborated to (-)-anisomycin 15 and (+)-polyoxamic acid 19.
Enantioselective Syntheses of (-)-Anisomycin and Its Propionate Derivative (3097-B1)
Shi, Zhi-cai,Lin, Guo-qiang
, p. 2907 - 2910 (2007/10/03)
Facile syntheses of (-)-anisomycin and 3097-B1 from divinylcarbinol 3 in an overall yield of 12.2percent and 13.2percent, respectively are described.
A New Synthesis of (-)-Anisomycin and its Demethoxy analogue from D-Ribose
Buchanan, J. Grant,MacLean, Keith A.,Wightman, Richard H.,Paulsen, Hans
, p. 1463 - 1470 (2007/10/02)
2,3-O-Isopropylidene-D-ribose (7) reacted with p-methoxybenzylmagnesium chloride in tetrahydrofuran to give the D-allotriol (6a) (77percent).Periodate oxidation of compound (6a) followed by reaction with hydroxylamine hydrochloride in pyridine gave (E,Z)-5-deoxy-2,3-O-isopropylidene-5-(p-methoxyphenyl)-L-ribose oxime (18a) which was converted into the nitrile methanesulphonate (19a) with methanesulphonyl chloride in pyridine.Reduction of the nitrile (19a) with lithium aluminium hydride gave (2R,3S,4R)-3,4-isopropylidenedioxy-2-(p-methoxybenzyl)pyrrolidine (2a) , which was converted into the epoxide (24a) (68percent) via the bromo acetates (28a) and (29a).Regioselective opening of the epoxide ring in compound (24a) with acidic allyl alcohol gave the allyl ether (30a) (63percent) which was converted into the N-benzyl 3-acetoxy compound (31a) (77percent).Removal of the allyl and benzyl groups, by treatment with palladium-charcoal under acidic conditions followed by hydrogenolysis, gave (-)-anisomycin (1a (86percent). A similar series of reactions afforded demethoxyanisomycin (1b) which showed antibiotic activity against Trichomonas vaginalis .
