1204-06-4 Usage
Description
3-Indoleacrylic acid (IAA) is a light yellow to yellow-beige crystalline powder that serves as a chemical inducer for gene transcription. It is particularly utilized in the context of the trpE promoter, which is a key component in the process of gene expression. This promoter is often cloned in plasmids containing the gene of interest, allowing for the controlled expression of specific genes.
Uses
Used in Molecular Biology and Genetic Engineering:
3-Indoleacrylic acid is used as an inducer for the expression of ribokinase in E. coli. This application is crucial in the field of molecular biology and genetic engineering, as it allows for the manipulation and study of gene expression in bacterial systems. By inducing the expression of specific genes, researchers can gain valuable insights into the functions and interactions of various genetic elements.
Used in Pharmaceutical Research:
As a chemical inducer, 3-Indoleacrylic acid can also be employed in the development of novel pharmaceutical compounds. By understanding how this compound interacts with specific genes and proteins, researchers can potentially design new drugs that target these genetic elements, leading to the development of more effective treatments for various diseases and conditions.
Used in Biotechnology:
In the field of biotechnology, 3-Indoleacrylic acid can be utilized for the production of recombinant proteins. By inducing the expression of specific genes, biotechnologists can produce large quantities of proteins with desired characteristics, which can then be used for various applications, such as the development of new drugs, vaccines, or diagnostic tools.
Used in Research and Development:
3-Indoleacrylic acid is also valuable in research and development settings, where it can be used to study the mechanisms of gene regulation and expression. This knowledge can be applied to develop new strategies for gene therapy, as well as to improve our understanding of the underlying causes of various genetic disorders.
Synthesis Reference(s)
Synthesis, p. 236, 1984 DOI: 10.1055/s-1984-30787
Biochem/physiol Actions
3-Indoleacrylic acid helps to block the mycelial growth of?Neurospora crassa. As a result, the cells accumulate indoleglycerol phosphate, which influences the rate of tryptophan synthetase.
Purification Methods
Recrystallise the acid from AcOH, H2O or EtOAc/cyclohexane. UV in MeOH has at 225, 274 and 325nm. [Shaw et al. J Org Chem 23 1171 1958, constitution: Rappe Acta max Chem Scand 18 818 1964, Moffatt J Chem Soc 1442 1957, Kimming et al. Hoppe Seyler's Z Physiol Chem 371 234 1958, Beilstein 22 V 249.]
Check Digit Verification of cas no
The CAS Registry Mumber 1204-06-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,0 and 4 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1204-06:
(6*1)+(5*2)+(4*0)+(3*4)+(2*0)+(1*6)=34
34 % 10 = 4
So 1204-06-4 is a valid CAS Registry Number.
InChI:InChI=1/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-30-23(11-38(54)55)20(4-8-35(48)49)28(42-30)16-32-24(12-39(56)57)21(5-9-36(50)51)29(43-32)15-31-22(10-37(52)53)19(3-7-34(46)47)27(41-31)13-25(17)40-26/h13-16,41-42H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-13-,28-16-,29-15-,30-14-,31-15-,32-16-
1204-06-4Relevant articles and documents
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Suvorov et al.
, (1968)
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Induction of Apoptosis in Hepatocellular Carcinoma Cell Lines by Novel Indolylacrylamide Derivatives: Synthesis and Biological Evaluation
Hawash, Mohammed,Kahraman, Deniz Cansen,Cetin-Atalay, Rengul,Baytas, Sultan Nacak
, (2021/04/28)
Hepatocellular carcinoma (HCC) is the most prevalent primary liver cancer and one of the leading causes of cancer associated death worldwide. This is due to the highly resistant nature of this malignancy and the lack of effective treatment options for advanced stage HCC patients. The hyperactivity of PI3K/Akt and Ras/Raf/MEK/ERK signaling pathways contribute to the cancer progression, survival, motility, and resistance mechanisms, and the interaction of these two pathways are responsible for the regulation of cancer cell growth and development. Therefore, it is vital to design and develop novel therapeutic options for HCC treatment targeting these hyperactive pathways. For this purpose, novel series of trans-indole-3-ylacrylamide derivatives originated from the lead compound, 3-(1H-indole-3-yl)-N-(3,4,5-trimethoxyphenyl)acrylamide, have been synthesized and analyzed for their bioactivity on cancer cells along with the lead compound. Based on the initial screening, the most potent compounds were selected to elucidate their effects on cellular signaling activity of HCC cell lines. Cell cycle analysis, immunofluorescence, and Western blot analysis revealed that lead compound and (E)-N-(4-tert-butylphenyl)-3-(1H-indole-3-yl)acrylamide induced cell cycle arrest at the G2/M phase, enhanced chromatin condensation and PARP-cleavage, addressing induction of apoptotic cell death. Additionally, these compounds decreased the activity of ERK signaling pathway, where phosphorylated ERK1/2 and c-Jun protein levels diminished significantly. Relevant to these findings, the lead compound was able to inhibit tubulin polymerization as well. To conclude, the novel trans-indole-3-ylacrylamide derivatives inhibit one of the critical pathways associated with HCC which results in cell cycle arrest and apoptosis in HCC cell lines.
Synthesis and antiinflammatory activity of indolylacrylic and methylacrylic acids
Andreani,Rambaldi,Locatelli,Pifferi
, p. 903 - 906 (2007/10/02)
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