Auxin - CAS 87-51-4

Chemical dimerizer used in auxin-inducible degron (AID) system; phytohormone.

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Molecular Formula
C10H9NO2
Molecular Weight
175.18

Auxin

    • Specification
      • Purity
        ≥ 98 % (HPLC)
        Solubility
        DMSO : 17.52mg/mL
        Appearance
        Solid powder
        Application
        Plant Growth Regulators
        Shelf Life
        Limited shelf life, expiry date on the label
        Storage
        Store at -20 °C
        Shipping
        Room temperature in continental US; may vary elsewhere.
        IUPAC Name
        2-(1H-indol-3-yl)acetic acid
        Synonyms
        Auxin; IAA; 3-Indoleacetic acid
    • Properties
      • Boiling Point
        164-165 °C
        Melting Point
        168.5 °C
        Density
        1.576 g/cm3
        Chemical Name
        1H-Indole-3-acetic acid
        InChI Key
        InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
        InChI
        SEOVTRFCIGRIMH-UHFFFAOYSA-N
        Canonical SMILES
        OC(CC1=CNC2=C1C=CC=C2)=O
        Stability
        Stable. Incompatible with strong oxidizing agents. Light sensitive.
        Biological Activity
        Chemical dimerizer used in auxin-inducible degron (AID) systems. Induces degradation of a target protein tagged with the auxin-receptor F-box protein Tir1 E3 ligase AID in human colorectral cancer and mouse ES cells or tagged with AFB2 in A431 cells. Endogenous plant hormone.
    • Reference Reading
      • 1.Auxin response under osmotic stress.
        Naser V1, Shani E2. Plant Mol Biol. 2016 Apr 6. [Epub ahead of print]
        The phytohormone auxin (indole-3-acetic acid, IAA) is a small organic molecule that coordinates many of the key processes in plant development and adaptive growth. Plants regulate the auxin response pathways at multiple levels including biosynthesis, metabolism, transport and perception. One of the most striking aspects of plant plasticity is the modulation of development in response to changing growth environments. In this review, we explore recent findings correlating auxin response-dependent growth and development with osmotic stresses. Studies of water deficit, dehydration, salt, and other osmotic stresses point towards direct and indirect molecular perturbations in the auxin pathway. Osmotic stress stimuli modulate auxin responses by affecting auxin biosynthesis (YUC, TAA1), transport (PIN), perception (TIR/AFB, Aux/IAA), and inactivation/conjugation (GH3, miR167, IAR3) to coordinate growth and patterning. In turn, stress-modulated auxin gradients drive physiological and developmental mechanisms such as stomata aperture, aquaporin and lateral root positioning.
        2.Hydrolases of the ILR1-like family of Arabidopsis thaliana modulate auxin response by regulating auxin homeostasis in the endoplasmic reticulum.
        Sanchez Carranza AP1, Singh A1, Steinberger K1, Panigrahi K2, Palme K1,3,4,5, Dovzhenko A1, Dal Bosco C1. Sci Rep. 2016 Apr 11;6:24212. doi: 10.1038/srep24212.
        Amide-linked conjugates of indole-3-acetic acid (IAA) have been identified in most plant species. They function in storage, inactivation or inhibition of the growth regulator auxin. We investigated how the major known endogenous amide-linked IAA conjugates with auxin-like activity act in auxin signaling and what role ILR1-like proteins play in this process in Arabidopsis. We used a genetically encoded auxin sensor to show that IAA-Leu, IAA-Ala and IAA-Phe act through the TIR1-dependent signaling pathway. Furthermore, by using the sensor as a free IAA reporter, we followed conjugate hydrolysis mediated by ILR1, ILL2 and IAR3 in plant cells and correlated the activity of the hydrolases with a modulation of auxin response. The conjugate preferences that we observed are in agreement with available in vitro data for ILR1. Moreover, we identified IAA-Leu as an additional substrate for IAR3 and showed that ILL2 has a more moderate kinetic performance than observed in vitro.
        3.MicroRNAs, polyamines, and the activities antioxidant enzymes are associated with in vitro rooting in white pine (Pinus strobus L.).
        Fei Y1, Xiao B1, Yang M1, Ding Q1, Tang W2. Springerplus. 2016 Apr 6;5:416. doi: 10.1186/s40064-016-2080-1. eCollection 2016.
        Molecular mechanism of in vitro rooting in conifer is not fully understood. After establishment of a regeneration procedure in eastern white pine (Pinus strobus L.) using mature embryos as explants to induce shoot formation on medium containing 3 μM IAA, 6 μM BA and 6 μM TDZ and induce root formation on medium containing 0.001-0.05 μM IAA, 0.001-0.05 μM IBA, 0.001-0.05 μM TDZ, we have investigated the changes of polyamine content and the activities of antioxidant enzymes during in vitro rooting in P. strobus. Our results demonstrated that putrescine (Put), spermidine (Spd), and spermine (Spm) did not increase in P. strobus during the first week of rooting on medium supplemented with 0.01 μM indole-3-acetic acid (IAA), whereas the levels of Put, Spd, and Spm increased during the 1st-3rd week of culture on medium with IAA, and then decreased on medium with IAA. No such a change in Put, Spd, and Spm was observed on medium without IAA. Measurement of antioxidant enzyme activity demonstrated that the activities of polyphenol oxidase, catalase, and peroxidase slightly increased in the first week of culture and reached to the highest peak in the 3rd-5th week of culture.
        4.Molecular Characterization of MaCCS, a Novel Copper Chaperone Gene Involved in Abiotic and Hormonal Stress Responses in Musa acuminata cv. Tianbaojiao.
        Feng X1, Chen F2, Liu W3, Thu MK4, Zhang Z5, Chen Y6, Cheng C7, Lin Y8, Wang T9, Lai Z10. Int J Mol Sci. 2016 Mar 24;17(4). pii: E441. doi: 10.3390/ijms17040441.
        Copper/zinc superoxide dismutases (Cu/ZnSODs) play important roles in improving banana resistance to adverse conditions, but their activities depend on the copper chaperone for superoxide dismutase (CCS) delivering copper to them. However, little is known about CCS in monocots and under stress conditions. Here, a novel CCS gene (MaCCS) was obtained from a banana using reverse transcription PCR and rapid-amplification of cDNA ends (RACE) PCR. Sequence analyses showed that MaCCS has typical CCS domains and a conserved gene structure like other plant CCSs. Alternative transcription start sites (ATSSs) and alternative polyadenylation contribute to the mRNA diversity of MaCCS. ATSSs in MaCCS resulted in one open reading frame containing two in-frame start codons to form two protein versions, which is supported by the MaCCS subcellular localization of in both cytosol and chloroplasts. Furthermore, MaCCS promoter was found to contain many cis-elements associated with abiotic and hormonal responses.
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