Anisomycin

Anisomycin is an antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: Z10-101-164

CAS No:22862-76-6

Synonyms/Alias:Flagecidin

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M.F/Formula
C14H19NO4
M.W/Mr.
265.31
Labeling Target
c-Jun N-terminal kinase (JNK)
Application
Anisomycin is used as a antineoplastic agent that inhibits or prevents the proliferation of neoplasms.
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Activity
Inhibitor
Biological Activity
Anisomycin is a potent protein synthesis inhibitor which interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system. Anisomycin is a JNK activator, which increases phospho-JNK. Anisomycin is a bacterial antibiotic.
Areas of Interest
Immunology & Inflammation
Cell Biology
Cancer
Functions
Anisomycin is inactive against bacteria.

Anisomycin is a potent antibiotic and protein synthesis inhibitor derived from Streptomyces griseolus, widely recognized for its significant role in molecular biology and biochemical research. Its unique mechanism of action, which involves the inhibition of peptidyl transferase activity on the 60S ribosomal subunit, makes it an invaluable tool for scientists investigating the regulation of protein synthesis and cellular responses to translational stress. The compound is characterized by its ability to rapidly halt protein production in eukaryotic cells, facilitating the dissection of intricate cellular pathways and providing insights into gene expression, signal transduction, and cellular adaptation. Researchers value its specificity and effectiveness in modulating cellular processes, making Anisomycin a cornerstone in experimental systems that require precise control of protein synthesis dynamics.

Signal Transduction Research: Anisomycin is extensively utilized in the study of intracellular signaling pathways, particularly those involving the activation of stress-activated protein kinases such as JNK and p38 MAPK. By inducing cellular stress through translational inhibition, it enables researchers to probe the upstream and downstream components of these pathways, elucidating the molecular mechanisms underlying cellular adaptation to environmental changes, DNA damage, and oxidative stress. The compound's ability to selectively activate specific kinases without affecting others provides a powerful approach for dissecting complex signaling networks and identifying potential regulatory nodes within the cell.

Gene Expression Regulation: In the field of gene expression, Anisomycin serves as a critical reagent for distinguishing between transcriptional and translational control mechanisms. By blocking new protein synthesis, it allows scientists to determine whether observed changes in mRNA levels are due to altered transcription or mRNA stability. This application is particularly valuable in studies of immediate-early genes, where rapid gene activation often precedes protein synthesis. The use of Anisomycin enables precise temporal analysis of gene regulatory events, supporting the development of models that describe how cells orchestrate coordinated responses to stimuli.

Neuroscience and Memory Research: Researchers in neuroscience employ Anisomycin to investigate the molecular basis of memory formation, synaptic plasticity, and neuronal signaling. Its ability to inhibit protein synthesis in neurons is instrumental in experiments designed to test the requirement for new proteins during long-term potentiation and memory consolidation. By administering the compound at specific time points, scientists can dissect the temporal requirements for protein synthesis in various phases of learning and memory, advancing our understanding of the cellular and molecular substrates of cognition.

Cellular Stress and Apoptosis Studies: The role of Anisomycin in inducing cellular stress responses extends to the study of apoptosis and programmed cell death. By triggering stress-activated protein kinases and inhibiting critical survival pathways, it provides a model for examining the molecular events that lead to cell fate decisions under adverse conditions. This application is particularly relevant for understanding the interplay between translation inhibition, stress signaling, and the activation of apoptotic pathways, offering insights into how cells maintain homeostasis or initiate self-destruction in response to damage.

Cancer Biology: In cancer research, Anisomycin is used to explore the dependence of rapidly dividing cells on protein synthesis and to study the mechanisms of translation control in tumor progression. Its capacity to differentially affect normal and transformed cells makes it a valuable tool for identifying vulnerabilities in cancer cells that rely heavily on protein synthesis for growth and survival. By integrating Anisomycin into experimental protocols, researchers can uncover new targets for therapeutic intervention and gain a deeper appreciation of the translational landscape in malignancies.

Developmental Biology: Anisomycin also finds application in developmental biology, where it is employed to investigate the timing and necessity of protein synthesis during critical stages of embryogenesis and tissue differentiation. By transiently inhibiting translation at specific developmental windows, scientists can determine the roles of newly synthesized proteins in morphogenesis, patterning, and cell fate specification. This approach contributes to a more nuanced understanding of how gene expression and protein synthesis are coordinated during organismal development, providing a foundation for further exploration of developmental processes and their regulation.

Long-term Storage Conditions
Soluble in DMSO
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage Conditions
Dry, dark and at 0 - 4 °C
Solubility
-20 °C
Organism
Human
InChI
InChI=1S/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/t12-,13+,14+/m1/s1
InChI Key
YKJYKKNCCRKFSL-RDBSUJKOSA-N
Isomeric SMILES
CC(=O)O[C@@H]1[C@H](CN[C@@H]1CC2=CC=C(C=C2)OC)O
BoilingPoint
398.7±42.0 °C at 760 mmHg
References

Anisomycin (2-p-methoxyphenylmethyl-3-acetoxy-4-hydroxypyrrolidine) inhibits protein synthesis in HeLa cells, rabbit reticulocytes, Saccharomyces fragilis, and cell-free extracts prepared from these sources, but it is inactive against extracts of Escherichia coli. Partial inhibition of deoxyribonucleic acid synthesis in HeLa cells is observed at anisomycin concentrations which produce 95% inhibition of protein synthesis. These effects on protein and DNA synthesis are rapid in onset and reversible. Anisomycin acts on the transfer reaction subsequent to the formation of aminoacyl transfer ribonucleic acid. In the presence of anisomycin, nascent peptide remains attached to polyribosomes. No derivative of anisomycin that was tested showed more than 1% of the inhibitory activity of the parent compound.

Inhibitors of Protein Biosynthesis II MODE OF ACTION OF ANISOMYCIN

Anisomycin is an immunosuppressant in low doses with possible application in treatment of some autoimmune diseases and in inhibiting transplantation rejection. Anisomycin suppresses malignant tumor cell growth and affects memory.

Investigation of electrochemical behavior of anisomycin on gold electrode followed by HPLC–MS/MS analysis

Melting Point
140-141ºC

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