Indole synthesis - Organic chemistry
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The second messenger cyclic guanosine 3′,5′-monophosphate (cGMP) plays an important role in plant development and responses to stress. Recent studies indicated that cGMP is a secondary signal generated in response to auxin stimulation. cGMP also mediates auxin-induced adventitious root formation in mung bean and gravitropic bending in soybean. Nonetheless, the mechanism of the participation of cGMP in auxin signalling to affect these growth and developmental processes is largely unknown. In this report we provide evidence that indole-3-acetic acid (IAA) induces cGMP accumulation in Arabidopsis roots through modulation of the guanylate cyclase activity. Application of 8-bromo-cGMP (a cell-permeable cGMP derivative) increases auxin-dependent lateral root formation, root hair development, primary root growth, and gene expression. In contrast, inhibitors of endogenous cGMP synthesis block these processes induced by auxin. Data also showed that 8-bromo-cGMP enhances auxin-induced degradation of Aux/IAA protein modulated by the SCFTIR1 ubiquitin-proteasome pathway. Furthermore, it was found that 8-bromo-cGMP is unable to directly influence the auxin-dependent TIR1-Aux/IAA interaction as evidenced by pull-down and yeast two-hybrid assays. In addition, we provide evidence for cGMP-mediated modulation of auxin signalling through cGMP-dependent protein kinase (PKG). Our results suggest that cGMP acts as a mediator to participate in auxin signalling and may govern this process by PKG activity via its inﬂuence on auxin-regulated gene expression and auxin/IAA degradation.
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The oxime is readily converted with base to the highly reactive species 1,1,1-trifluoro-2-nitroso-2-propene, which undergoes hetero-Diels-Alder reactions, e.g. with cyclopentadiene or indole to give fused oxazolines. The indole adduct rearomatizes to give 1-(3-indolyl)-3,3,3-trifluoroacetoxime: J. Org. Chem., 57, 339 (1992). Hiraoka, Y.; Kawasaki-Takasuka, T.; Morizawa, Y.; Yamazaki, T. Synthetic utility of 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf). J. Fluorine Chem. 2015, 179, 71-76.Dalmal, T.; Appalanaidu, K.; Kosurkar, U. B.; Jagadeesh Babu, N.; Kumbhare, R. M. One-Pot Synthesis of 2-Imino-4-(trifluoromethyl)thiazolidin-4-ol Derivatives in a Three-Component Reaction: Application to Structurally Diverse Scaffolds of Biological Interest Through Subsequent Reactions. Eur. J. Org. Chem. 2014, 2014 (12), 2468-2479.
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It is well known that PKG is also a regulator of protein activation. Thus, it is plausible that cGMP inﬂuences TIR1–Aux/IAA interaction through the PKG and that PKG is able to modify TIR1 activity, although findings from this study cannot directly prove this issue. However, it is worth addressing in a future work. In order to further test the hypothesis, the putative inhibitor of PKG, Rp-8-Br-cGMP, was used to examine whether the cGMP-mediated expression of auxin-responsive genes and degradation of the AXR3NT-GUS fusion protein is dependent on PKG activity. As expected, our data showed that the inhibition of PKG activity strongly blocked the auxin responses (), suggesting that cGMP might inﬂuence auxin signalling in Arabidopsis roots through PKG activity. This conclusion is in agreement with previous findings that cGMP as a mediator participates in photoperiodic ﬂowering induction in Pharbitis nil () and auxin-induced stomatal opening in Arabidopsis via its inﬂuence on PKG activity (). In addition, it has been demonstrated that AGC kinases are required for auxin-related processes such as auxin-mediated root development and organogenesis in Arabidopsis (; ). PKG is a component of AGC kinases, which further complement our conclusion that the cGMP-mediated auxin response is dependent on PKG activity.
TIR1 as the auxin-recognition component of the SCF complex that interacts with Aux/IAA proteins to target them for proteolysis has been illustrated in detail (; ; ). Recent work has shown that the amount of endogenous TIR1 protein appeared to be rate-limiting for auxin response and excess TIR1 protein in 35S::TIR1 even led to the degradation of Aux/IAAs in the absence of auxin treatment (). In addition, the discovery that inositol hexakisphosphate is associated with the TIR1 protein () suggests that TIR1 activity might be regulated by additional cofactors. All these findings suggest that TIR1 activity and its interaction with Aux/IAA proteins play a crucial role in auxin responses. Hence we focused on the effect of cGMP on interaction between TIR1 and Aux/IAA proteins. However, further molecular evidence showed that cGMP could not alter the auxin-enhanced interaction between TIR1 and Aux/IAAs, suggesting that cGMP did not directly alter the binding between TIR1 and its ligand, auxin (). Previous studies have shown that TIR1 is a member of a small gene family that contains ﬁve additional AFB proteins that all function as auxin receptors (; ). The functional defects of TIR1 protein evoke the reduction in auxin response. Moreover, the SCF complex mutants axr1-3 and axr1-12 also showed alteration of responses to auxin (; ) and Aux/IAA proteins exhibit increased stability in axr1 and tir1 mutants (). In addition, our results showed that the tir1-1, axr1-3, and axr1-12 mutants displayed reduced sensitivity to LY83583 and 8-Br-cGMP on auxin-inhibited primary root elongation (), suggesting that cGMP might be involved in SCFTIR1/AFB signalling. Thus, it is possible that cGMP alters the interaction of other AFB proteins with Aux/IAA proteins or TIR1–Aux/IAA interaction via downstream effectors of cGMP signalling, such as PKG.
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It is well known that MG132 blocks the degradation of Aux/IAA protein by repressing the proteasome activity in Arabidopsis (). Similarly to MG132, our results showed that the inhibition of cGMP synthesis strongly inhibited the degradation of Aux/IAA protein (). Therefore, we further examined whether the effects of cGMP was related to the ATP-dependent 26S proteasome activity. It was shown that exogenous 8-Br-cGMP increased and LY83583 strongly suppressed the ATP-dependent proteasome activity in Arabidopsis roots, respectively (). These results further confirmed that cGMP acted on the auxin signalling pathway through the SCFTIR1-mediated degradation of Aux/IAAs. However, we found that repression of the proteasome activity using MG132 could not block the action of cGMP on IAA-induced LR formation in Arabidopsis roots, suggesting that cGMP promotes auxin-induced LR formation by a proteasome-independent mechanism (). These seemingly paradoxical results of cGMP action are similar to nitric oxide (NO), which was reported to be involved in the auxin signalling through Aux/IAA degradation (), whereas it promotes reduction of PIN1 protein levels by a proteasome-independent mechanism (). In addition, we also noticed that the inhibition of proteasome activity could not entirely repress the effect of auxin on LR formation (), suggesting that the effect of cGMP on auxin-induced LR formation might be involved much more complicated mechanisms. Taking into account all these ﬁndings, we propose that cGMP might operate in multiple ways, including the dependent as well as independent regulation of proteasome-dependent Aux/IAA ubiquitination and subsequent degradation.
The oxime is readily converted with base to the highly reactive species 1,1,1-trifluoro-2-nitroso-2-propene, which undergoes hetero-Diels-Alder reactions, e.g. with cyclopentadiene or indole to give fused oxazolines. The indole adduct rearomatizes to give 1-(3-indolyl)-3,3,3-trifluoroacetoxime: J. Org. Chem., 57, 339 (1992).
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As previously reported in other plant species, our results showed that IAA induces endogenous cGMP accumulation in Arabidopsis roots (). A recent study using the ﬂuorescent reporter FlincG as an endogenous cGMP sensor also showed that auxin rapidly increased cellular cGMP within a short period of time in Arabidopsis protoplast (), and which was consistent with our results. Moreover, IAA could markedly induce GC activity in a concentration-dependent manner in Arabidopsis roots (). It has been reported that cGMP accumulation was attributable to activation of GC rather than 3′,5′-cyclic-cGMP phosphodiesterase in ABA-mediated stomatal movement (). These results suggest that auxin could increase the endogenous cGMP levels by affecting GC activity in Arabidopsis roots.
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As reported previously, PKG, consisting of a cyclic nucleotide-binding domain and a protein kinase domain, is a typical downstream cellular target or effector of cGMP modulation in animals and plants (; ). Therefore, cGMP may affect auxin signalling via PKG action. To address this possibility we used Rp-8-Br-cGMP, a putative inhibitor of PKG. This reagent selectively inhibits the PKG activity in animal cells and auxin-induced stomatal opening in Arabidopsis (; ). As shown in and , we observed that pretreatment with 100 μM Rp-8-Br-cGMP blocked expression – induced by either IAA alone or IAA plus 8-Br-cGMP – of these auxin-responsive genes, including DR5::GUS reporter, IAA5, and IAA11. In addition, it also seriously abolished the degradation – induced by IAA alone or IAA plus 8-Br-cGMP – of the AXR3NT-GUS fusion protein (). These results strongly suggest that cGMP-mediated modulation of auxin signalling is dependent on the PKG activity in Arabidopsis.
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The plant hormone auxin plays a central role in plant responses to physiological and environmental changes. It regulates cell division and differentiation, embryogenesis, organogenesis, phototropic and gravitropic responses, and root and shoot architecture formation (; ). Optimal post-embryonic root growth requires tight control of indole-3-acetic acid (IAA) activity, which can be regulated by diverse mechanisms including IAA biosynthesis, its transport, and signal transduction ().
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