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Indole-3-acetic acid

February 16, 2024

Indole-3-acetic acid (IAA, 3-IAA) is the most common naturally occurring plant hormone of the auxin class. It is the best known of the auxins, and has been the subject of extensive studies by plant physiologists.[1] IAA is a derivative of indole, containing a carboxymethyl substituent. It is a colorless solid that is soluble in polar organic solvents.

Indole-3-acetic acid
Names
Preferred IUPAC name
(1H-Indol-3-yl)acetic acid
Other names
Indole-3-acetic acid,
indolylacetic acid,
1H-Indole-3-acetic acid,
indoleacetic acid,
heteroauxin,
IAA
Identifiers
  • 87-51-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16411 Y
ChEMBL
  • ChEMBL82411 Y
ChemSpider
  • 780 Y
DrugBank
  • DB07950 Y
ECHA InfoCard 100.001.590
KEGG
  • C00954 Y
  • 802
UNII
  • 6U1S09C61L Y
  • DTXSID5020738
  • 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) Y
    Key: SEOVTRFCIGRIMH-UHFFFAOYSA-N Y
  • InChI=1/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
    Key: SEOVTRFCIGRIMH-UHFFFAOYAT
  • O=C(O)Cc1c[nH]c2ccccc12
Properties
C10H9NO2
Molar mass 175.187 g·mol−1
Appearance White solid
Melting point 168 to 170 °C (334 to 338 °F; 441 to 443 K)
insoluble in water. Soluble in ethanol to 50mg/ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Biosynthesis edit

Main article: Auxin

IAA is predominantly produced in cells of the apex (bud) and very young leaves of a plant. Plants can synthesize IAA by several independent biosynthetic pathways. Four of them start from tryptophan, but there is also a biosynthetic pathway independent of tryptophan.[2] Plants mainly produce IAA from tryptophan through indole-3-pyruvic acid.[3][4] IAA is also produced from tryptophan through indole-3-acetaldoxime in Arabidopsis thaliana.[5]

In rats, IAA is a product of both endogenous and colonic microbial metabolism from dietary tryptophan along with tryptophol. This was first observed in rats infected by Trypanosoma brucei gambiense.[6] A 2015 experiment showed that a high-tryptophan diet can decrease serum levels of IAA in mice, but that in humans, protein consumption has no reliably predictable effect on plasma IAA levels.[7] Human cells have been known to produce IAA in vitro since the 1950s,[8] and the critical biosynthesis gene IL4I1 has been identified.[9][10]

Biological effects edit

As all auxins, IAA has many different effects, such as inducing cell elongation and cell division with all subsequent results for plant growth and development. On a larger scale, IAA serves as signaling molecule necessary for development of plant organs and coordination of growth.

Plant gene regulation edit

IAA enters the plant cell nucleus and binds to a protein complex composed of a ubiquitin-activating enzyme (E1), a ubiquitin-conjugating enzyme (E2), and a ubiquitin ligase (E3), resulting in ubiquitination of Aux/IAA proteins with increased speed.[11] Aux/IAA proteins bind to auxin response factor (ARF) proteins, forming a heterodimer, suppressing ARF activity.[12] In 1997 it was described how ARFs bind to auxin-response gene elements in promoters of auxin regulated genes, generally activating transcription of that gene when an Aux/IAA protein is not bound.[13]

IAA inhibits the photorespiratory-dependent cell death in photorespiratory catalase mutants. This suggests a role for auxin signalling in stress tolerance.[14]

Bacterial physiology edit

IAA production is widespread among environmental bacteria that inhabit soils, waters, but also plant and animal hosts. Distribution and substrate specificity of the involved enzymes suggests these pathways play a role beyond plant-microbe interactions.[15] Enterobacter cloacae can produce IAA, from aromatic and branched-chain amino acids.[16]

Fungal symbiosis edit

Fungi can form a fungal mantle around roots of perennial plants called ectomycorrhiza. A fungus specific to spruce called Tricholoma vaccinum was shown to produce IAA from tryptophan and excrete it from its hyphae. This induced branching in cultures, and enhanced Hartig net formation. The fungus uses a multidrug and toxic extrusion (MATE) transporter Mte1.[17] Research into IAA-producing fungi to promote plant growth and protection in sustainable agriculture is underway.[18]

Skatole biosynthesis edit

Skatole, the odorant in feces, is produced from tryptophan via indoleacetic acid. Decarboxylation gives the methylindole.[19][20]

Synthesis edit

Chemically, it can be synthesized by the reaction of indole with glycolic acid in the presence of base at 250 °C:[21]

 

Alternatively the compound has been synthesized by Fischer indole synthesis using glutamic acid and phenylhydrazine.[22] Glutamic acid was converted to the necessary aldehyde via Strecker degradation.

Many methods for its synthesis have been developed since its original synthesis from indole-3-acetonitrile.[23]

History and synthetic analogs edit

William Gladstone Tempelman studied substances for growth promotion at Imperial Chemical Industries Ltd. After 7 years of research he changed the direction of his study to try the same substances at high concentrations in order to stop plant growth. In 1940 he published his finding that IAA killed broadleaf plants within a cereal field.[24]

The search for an acid with a longer half life, i.e. a metabolically and environmentally more stable compound led to 2,4-dichlorophenoxyacetic acid (2,4-D) and 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), both phenoxy herbicides and analogs of IAA. Robert Pokorny an industrial chemist for the C.B. Dolge Company in Westport, Connecticut published their synthesis in 1941.[25] When sprayed on broad-leaf dicot plants, they induce rapid, uncontrolled growth, eventually killing them. First introduced in 1946, these herbicides were in widespread use in agriculture by the middle of the 1950s.[citation needed]

Other less expensive synthetic auxin analogs on the market for use in horticulture are indole-3-butyric acid (IBA) and 1-naphthaleneacetic acid (NAA).[26]

Mammalian toxicity/health effects edit

Little research has been conducted on the effects of IAA on humans and toxicity data are limited. No data on human carcinogenic, teratogenic, or developmental effects have been created.

IAA is listed in its MSDS as mutagenic to mammalian somatic cells, and possibly carcinogenic based on animal data. It may cause adverse reproductive effects (fetotoxicity) and birth defects based on animal data. No human data as of 2008.[27] It is listed as a potential skin, eye, and respiratory irritant, and users are warned not to ingest it. Protocols for ingestion, inhalation, and skin/eye exposure are standard for moderately poisonous compounds and include thorough rinsing in the case of skin and eyes, fresh air in the case of inhalation, and immediately contacting a physician in all cases to determine the best course of action and not to induce vomiting when of ingested. The NFPA 704 health hazard rating for IAA is 2, which denotes a risk of temporary incapacitation with intense or prolonged, but not chronic exposure, and a possibility of residual injury.[28] IAA is a direct ligand of the aryl hydrocarbon receptor,[29] and IAA treatment of mice indicate liver-protective effects in a model of non-alcoholic fatty liver disease.[30] Humans typically have relatively high levels of IAA in their serum (~1µM), but this can be increased further in certain disease conditions and can be a poor prognostic marker for cardiovascular health.[31] Whether this IAA originates from endogenous biosynthesis via IL4I1 or gut microbiota is unknown. A 2021 study found that normal mice had an average of 3.7 times as much IAA in their feces compared to germ-free mice, suggesting that the mammalian microbiome contributes significantly to the overall circulating amount. [32]

Developmental toxicity edit

IAA produces microcephaly in rats during the early stage of cerebral cortex development. IAA treatment of pregnant rats, at a dose of 1 gram per kg of body weight per day, decreased the locomotor activities of rat embryos/fetuses; treatment with IAA and analog 1(methyl)-IAA resulted in apoptosis of neuroepithelial cell and significantly decreased brain sizes relative to body weight in embryonic rats.[33]

Immunotoxin edit

IAA is an apoptosis-inducing ligand in mammals. As of 2010, the signal transduction pathways are as follows: IAA/HRP activates p38 mitogen-activated protein kinases and c-Jun N-terminal kinases. It induces caspase-8 and caspase-9, which results in caspase-3 activation and poly(adp-ribose) polymerases cleavage.[34]

In 2002 it had been hypothesized that IAA coupled with horseradish peroxidase (HRP) could be used in targeted cancer therapy. Radical-IAA molecules would attach to cells marked by HRP and HRP reactive cells would be selectively killed.[35] In 2010 in vitro experiments proved this concept of IAA as an immunotoxin when used in preclinical studies of targeted cancer therapy, as it induced apoptosis in bladder[34] and in hematological malignancies.[36]

References edit

 
Wikimedia Commons has media related to Indole acetic acid.
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  2. ^ Zhao, Yunde (2010). "Auxin Biosynthesis and Its Role in Plant Development". Annual Review of Plant Biology. 61: 49–64. doi:10.1146/annurev-arplant-042809-112308. PMC 3070418. PMID 20192736.
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  5. ^ Sugawara, Satoko; Hishiyama, Shojiro; Jikumaru, Yusuke; Hanada, Atsushi; Nishimura, Takeshi; Koshiba, Tomokazu; Zhao, Yunde; Kamiya, Yuji; Kasahara, Hiroyuki (2009). "Biochemical analyses of indole-3-acetaldoxime-dependent auxin biosynthesis in Arabidopsis". Proceedings of the National Academy of Sciences. 106 (13): 5430–5. Bibcode:2009PNAS..106.5430S. doi:10.1073/pnas.0811226106. JSTOR 40455212. PMC 2664063. PMID 19279202.
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  17. ^ Krause K, Henke C, Asiimwe T, Ulbricht A, Klemmer S, Schachtschabel D, Boland W, Kothe E (Oct 2015). "Biosynthesis and Secretion of Indole-3-Acetic Acid and Its Morphological Effects on Tricholoma vaccinum-Spruce Ectomycorrhiza". Appl Environ Microbiol. 81 (20): 7003–11. Bibcode:2015ApEnM..81.7003K. doi:10.1128/AEM.01991-15. PMC 4579454. PMID 26231639.
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  30. ^ Ji, Yun; Gao, Yuan; Chen, Hong; Yin, Yue; Zhang, Weizhen (2019-09-03). "Indole-3-Acetic Acid Alleviates Nonalcoholic Fatty Liver Disease in Mice via Attenuation of Hepatic Lipogenesis, and Oxidative and Inflammatory Stress". Nutrients. 11 (9): 2062. doi:10.3390/nu11092062. ISSN 2072-6643. PMC 6769627. PMID 31484323.
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February 16, 2024
indole, acetic, acid, most, common, naturally, occurring, plant, hormone, auxin, class, best, known, auxins, been, subject, extensive, studies, plant, physiologists, derivative, indole, containing, carboxymethyl, substituent, colorless, solid, that, soluble, p. Indole 3 acetic acid IAA 3 IAA is the most common naturally occurring plant hormone of the auxin class It is the best known of the auxins and has been the subject of extensive studies by plant physiologists 1 IAA is a derivative of indole containing a carboxymethyl substituent It is a colorless solid that is soluble in polar organic solvents Indole 3 acetic acid NamesPreferred IUPAC name 1H Indol 3 yl acetic acidOther names Indole 3 acetic acid indolylacetic acid 1H Indole 3 acetic acid indoleacetic acid heteroauxin IAAIdentifiersCAS Number 87 51 4 Y3D model JSmol Interactive imageChEBI CHEBI 16411 YChEMBL ChEMBL82411 YChemSpider 780 YDrugBank DB07950 YECHA InfoCard 100 001 590KEGG C00954 YPubChem CID 802UNII 6U1S09C61L YCompTox Dashboard EPA DTXSID5020738InChI 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 YKey SEOVTRFCIGRIMH UHFFFAOYSA N YInChI 1 C10H9NO2 c12 10 13 5 7 6 11 9 4 2 1 3 8 7 9 h1 4 6 11H 5H2 H 12 13 Key SEOVTRFCIGRIMH UHFFFAOYATSMILES O C O Cc1c nH c2ccccc12PropertiesChemical formula C 10H 9N O 2Molar mass 175 187 g mol 1Appearance White solidMelting point 168 to 170 C 334 to 338 F 441 to 443 K Solubility in water insoluble in water Soluble in ethanol to 50mg mlExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Biosynthesis 2 Biological effects 2 1 Plant gene regulation 2 2 Bacterial physiology 2 3 Fungal symbiosis 2 4 Skatole biosynthesis 3 Synthesis 4 History and synthetic analogs 5 Mammalian toxicity health effects 5 1 Developmental toxicity 5 2 Immunotoxin 6 ReferencesBiosynthesis editMain article Auxin IAA is predominantly produced in cells of the apex bud and very young leaves of a plant Plants can synthesize IAA by several independent biosynthetic pathways Four of them start from tryptophan but there is also a biosynthetic pathway independent of tryptophan 2 Plants mainly produce IAA from tryptophan through indole 3 pyruvic acid 3 4 IAA is also produced from tryptophan through indole 3 acetaldoxime in Arabidopsis thaliana 5 In rats IAA is a product of both endogenous and colonic microbial metabolism from dietary tryptophan along with tryptophol This was first observed in rats infected by Trypanosoma brucei gambiense 6 A 2015 experiment showed that a high tryptophan diet can decrease serum levels of IAA in mice but that in humans protein consumption has no reliably predictable effect on plasma IAA levels 7 Human cells have been known to produce IAA in vitro since the 1950s 8 and the critical biosynthesis gene IL4I1 has been identified 9 10 Biological effects editAs all auxins IAA has many different effects such as inducing cell elongation and cell division with all subsequent results for plant growth and development On a larger scale IAA serves as signaling molecule necessary for development of plant organs and coordination of growth Plant gene regulation edit IAA enters the plant cell nucleus and binds to a protein complex composed of a ubiquitin activating enzyme E1 a ubiquitin conjugating enzyme E2 and a ubiquitin ligase E3 resulting in ubiquitination of Aux IAA proteins with increased speed 11 Aux IAA proteins bind to auxin response factor ARF proteins forming a heterodimer suppressing ARF activity 12 In 1997 it was described how ARFs bind to auxin response gene elements in promoters of auxin regulated genes generally activating transcription of that gene when an Aux IAA protein is not bound 13 IAA inhibits the photorespiratory dependent cell death in photorespiratory catalase mutants This suggests a role for auxin signalling in stress tolerance 14 Bacterial physiology edit IAA production is widespread among environmental bacteria that inhabit soils waters but also plant and animal hosts Distribution and substrate specificity of the involved enzymes suggests these pathways play a role beyond plant microbe interactions 15 Enterobacter cloacae can produce IAA from aromatic and branched chain amino acids 16 Fungal symbiosis edit Fungi can form a fungal mantle around roots of perennial plants called ectomycorrhiza A fungus specific to spruce called Tricholoma vaccinum was shown to produce IAA from tryptophan and excrete it from its hyphae This induced branching in cultures and enhanced Hartig net formation The fungus uses a multidrug and toxic extrusion MATE transporter Mte1 17 Research into IAA producing fungi to promote plant growth and protection in sustainable agriculture is underway 18 Skatole biosynthesis edit Skatole the odorant in feces is produced from tryptophan via indoleacetic acid Decarboxylation gives the methylindole 19 20 Synthesis editChemically it can be synthesized by the reaction of indole with glycolic acid in the presence of base at 250 C 21 nbsp Alternatively the compound has been synthesized by Fischer indole synthesis using glutamic acid and phenylhydrazine 22 Glutamic acid was converted to the necessary aldehyde via Strecker degradation Many methods for its synthesis have been developed since its original synthesis from indole 3 acetonitrile 23 History and synthetic analogs editWilliam Gladstone Tempelman studied substances for growth promotion at Imperial Chemical Industries Ltd After 7 years of research he changed the direction of his study to try the same substances at high concentrations in order to stop plant growth In 1940 he published his finding that IAA killed broadleaf plants within a cereal field 24 The search for an acid with a longer half life i e a metabolically and environmentally more stable compound led to 2 4 dichlorophenoxyacetic acid 2 4 D and 2 4 5 trichlorophenoxyacetic acid 2 4 5 T both phenoxy herbicides and analogs of IAA Robert Pokorny an industrial chemist for the C B Dolge Company in Westport Connecticut published their synthesis in 1941 25 When sprayed on broad leaf dicot plants they induce rapid uncontrolled growth eventually killing them First introduced in 1946 these herbicides were in widespread use in agriculture by the middle of the 1950s citation needed Other less expensive synthetic auxin analogs on the market for use in horticulture are indole 3 butyric acid IBA and 1 naphthaleneacetic acid NAA 26 Mammalian toxicity health effects editLittle research has been conducted on the effects of IAA on humans and toxicity data are limited No data on human carcinogenic teratogenic or developmental effects have been created IAA is listed in its MSDS as mutagenic to mammalian somatic cells and possibly carcinogenic based on animal data It may cause adverse reproductive effects fetotoxicity and birth defects based on animal data No human data as of 2008 27 It is listed as a potential skin eye and respiratory irritant and users are warned not to ingest it Protocols for ingestion inhalation and skin eye exposure are standard for moderately poisonous compounds and include thorough rinsing in the case of skin and eyes fresh air in the case of inhalation and immediately contacting a physician in all cases to determine the best course of action and not to induce vomiting when of ingested The NFPA 704 health hazard rating for IAA is 2 which denotes a risk of temporary incapacitation with intense or prolonged but not chronic exposure and a possibility of residual injury 28 IAA is a direct ligand of the aryl hydrocarbon receptor 29 and IAA treatment of mice indicate liver protective effects in a model of non alcoholic fatty liver disease 30 Humans typically have relatively high levels of IAA in their serum 1µM but this can be increased further in certain disease conditions and can be a poor prognostic marker for cardiovascular health 31 Whether this IAA originates from endogenous biosynthesis via IL4I1 or gut microbiota is unknown A 2021 study found that normal mice had an average of 3 7 times as much IAA in their feces compared to germ free mice suggesting that the mammalian microbiome contributes significantly to the overall circulating amount 32 Developmental toxicity edit IAA produces microcephaly in rats during the early stage of cerebral cortex development IAA treatment of pregnant rats at a dose of 1 gram per kg of body weight per day decreased the locomotor activities of rat embryos fetuses treatment with IAA and analog 1 methyl IAA resulted in apoptosis of neuroepithelial cell and significantly decreased brain sizes relative to body weight in embryonic rats 33 Immunotoxin edit IAA is an apoptosis inducing ligand in mammals As of 2010 the signal transduction pathways are as follows IAA HRP activates p38 mitogen activated protein kinases and c Jun N terminal kinases It induces caspase 8 and caspase 9 which results in caspase 3 activation and poly adp ribose polymerases cleavage 34 In 2002 it had been hypothesized that IAA coupled with horseradish peroxidase HRP could be used in targeted cancer therapy Radical IAA molecules would attach to cells marked by HRP and HRP reactive cells would be selectively killed 35 In 2010 in vitro experiments proved this concept of IAA as an immunotoxin when used in preclinical studies of targeted cancer therapy as it induced apoptosis in bladder 34 and in hematological malignancies 36 References edit nbsp Wikimedia Commons has media related to Indole acetic acid Simon Sibu Petrasek Jan 2011 Why plants need more than one type of auxin Plant Science 180 3 454 60 doi 10 1016 j plantsci 2010 12 007 PMID 21421392 Zhao Yunde 2010 Auxin Biosynthesis and Its Role in Plant Development Annual Review of Plant Biology 61 49 64 doi 10 1146 annurev arplant 042809 112308 PMC 3070418 PMID 20192736 Mashiguchi Kiyoshi Tanaka Keita Sakai Tatsuya Sugawara Satoko Kawaide Hiroshi Natsume Masahiro Hanada Atsushi Yaeno Takashi et al 2011 The main auxin biosynthesis pathway in Arabidopsis Proceedings of the National Academy of Sciences 108 45 18512 7 Bibcode 2011PNAS 10818512M doi 10 1073 pnas 1108434108 PMC 3215075 PMID 22025724 Won Christina Shen Xiangling Mashiguchi Kiyoshi Zheng Zuyu Dai Xinhua Cheng Youfa Kasahara Hiroyuki Kamiya Yuji et al 2011 Conversion of tryptophan to indole 3 acetic acid by TRYPTOPHAN AMINOTRANSFERASES OF ARABIDOPSIS and YUCCAs in Arabidopsis Proceedings of the National Academy of Sciences 108 45 18518 23 Bibcode 2011PNAS 10818518W doi 10 1073 pnas 1108436108 PMC 3215067 PMID 22025721 Sugawara Satoko Hishiyama Shojiro Jikumaru Yusuke Hanada Atsushi Nishimura Takeshi Koshiba Tomokazu Zhao Yunde Kamiya Yuji Kasahara Hiroyuki 2009 Biochemical analyses of indole 3 acetaldoxime dependent auxin biosynthesis in Arabidopsis Proceedings of the National Academy of Sciences 106 13 5430 5 Bibcode 2009PNAS 106 5430S doi 10 1073 pnas 0811226106 JSTOR 40455212 PMC 2664063 PMID 19279202 Howard Stibbs Henry Richard Seed John 1975 Short Term Metabolism of 14C Tryptophan in Rats Infected with Trypanosoma brucei gambiense J Infect Dis 131 4 459 462 doi 10 1093 infdis 131 4 459 PMID 1117200 Poesen R Mutsaers HA et al Oct 2015 The Influence of Dietary Protein Intake on Mammalian Tryptophan and Phenolic Metabolites PLOS ONE 10 10 e0140820 Bibcode 2015PLoSO 1040820P doi 10 1371 journal pone 0140820 PMC 4607412 PMID 26469515 Weissbach H King W Sjoerdsma A Udenfriend S January 1959 Formation of indole 3 acetic acid and tryptamine in animals a method for estimation of indole 3 acetic acid in tissues The Journal of Biological Chemistry 234 1 81 86 doi 10 1016 S0021 9258 18 70339 6 ISSN 0021 9258 PMID 13610897 Zhang Xia Gan Min Li Jingyun Li Hui Su Meicheng Tan Dongfei Wang Shaolei Jia Man Zhang Liguo Chen Gang 2020 08 31 An endogenous indole pyruvate pathway for tryptophan metabolism mediated by IL4I1 Journal of Agricultural and Food Chemistry 68 39 10678 10684 doi 10 1021 acs jafc 0c03735 ISSN 1520 5118 PMID 32866000 S2CID 221402986 Sadik Ahmed Somarribas Patterson Luis F Ozturk Selcen Mohapatra Soumya R Panitz Verena Secker Philipp F Pfander Pauline Loth Stefanie Salem Heba Prentzell Mirja Tamara Berdel Bianca Iskar Murat Faessler Erik Reuter Friederike Kirst Isabelle Kalter Verena Foerster Kathrin I Jager Evelyn Guevara Carina Ramallo Sobeh Mansour Hielscher Thomas Poschet Gernot Reinhardt Annekathrin Hassel Jessica C Zapatka Marc Hahn Udo von Deimling Andreas Hopf Carsten Schlichting Rita Escher Beate I Burhenne Jurgen Haefeli Walter E Ishaque Naveed Bohme Alexander Schauble Sascha Thedieck Kathrin Trump Saskia Seiffert Martina Opitz Christiane A 2020 08 17 IL4I1 Is a Metabolic Immune Checkpoint that Activates the AHR and Promotes Tumor Progression Cell 182 5 1252 1270 e34 doi 10 1016 j cell 2020 07 038 ISSN 1097 4172 PMID 32818467 S2CID 221179265 Pekker MD Deshaies RJ 2005 Function and regulation of cullin RING ubiquitin ligases PDF Plant Cell 6 1 9 20 doi 10 1038 nrm1547 PMID 15688063 S2CID 24159190 Tiwari SB Hagen G Guilfoyle TJ 2004 Aux IAA proteins contain a potent transcriptional repression domain Plant Cell 16 2 533 43 doi 10 1105 tpc 017384 PMC 341922 PMID 14742873 Ulmasov T Hagen G Guilfoyle TJ 1997 ARF1 a transcription factor that binds to auxin response elements Science 276 5320 1865 68 doi 10 1126 science 276 5320 1865 PMID 9188533 Kerchev P Muhlenbock P Denecker J Morreel K Hoeberichts FA van der Kelen K Vandorpe M Nguyen L Audenaert D van Breusegem F Feb 2015 Activation of auxin signalling counteracts photorespiratory H2O2 dependent cell death Plant Cell Environ 38 2 253 65 doi 10 1111 pce 12250 PMID 26317137 Patten CL Blakney AJ Coulson TJ Nov 2013 Activity distribution and function of indole 3 acetic acid biosynthetic pathways in bacteria Crit Rev Microbiol 39 4 395 415 doi 10 3109 1040841X 2012 716819 PMID 22978761 S2CID 22123626 Parsons CV Harris DM Patten CL et al Sep 2015 Regulation of indole 3 acetic acid biosynthesis by branched chain amino acids in Enterobacter cloacae UW5 FEMS Microbiol Lett 362 18 fnv153 doi 10 1093 femsle fnv153 PMID 26347301 Krause K Henke C Asiimwe T Ulbricht A Klemmer S Schachtschabel D Boland W Kothe E Oct 2015 Biosynthesis and Secretion of Indole 3 Acetic Acid and Its Morphological Effects on Tricholoma vaccinum Spruce Ectomycorrhiza Appl Environ Microbiol 81 20 7003 11 Bibcode 2015ApEnM 81 7003K doi 10 1128 AEM 01991 15 PMC 4579454 PMID 26231639 Fu SF Wei JY Chen HW Liu YY Lu HY Chou JY Aug 2015 Indole 3 acetic acid A widespread physiological code in interactions of fungi with other organisms Plant Signal Behav 10 8 e1048052 doi 10 1080 15592324 2015 1048052 PMC 4623019 PMID 26179718 Whitehead T R Price N P Drake H L Cotta M A 25 January 2008 Catabolic pathway for the production of skatole and indoleacetic acid by the acetogen Clostridium drakei Clostridium scatologenes and swine manure Applied and Environmental Microbiology 74 6 1950 3 Bibcode 2008ApEnM 74 1950W doi 10 1128 AEM 02458 07 PMC 2268313 PMID 18223109 Yokoyama M T Carlson J R 1979 Microbial metabolites of tryptophan in the intestinal tract with special reference to skatole The American Journal of Clinical Nutrition 32 1 173 178 doi 10 1093 ajcn 32 1 173 PMID 367144 Johnson Herbert E Crosby Donald G 1964 Indole 3 acetic Acid Organic Syntheses 44 64 Collective Volume vol 5 p 654 Fox Sidney W Bullock Milon W 1951 Synthesis of Indoleacetic Acid from Glutamic Acid and a Proposed Mechanism for the Conversion Journal of the American Chemical Society 73 6 2754 2755 doi 10 1021 ja01150a094 Majima Rikō Hoshino Toshio 1925 Synthetische Versuche in der Indol Gruppe VI Eine neue Synthese von b Indolyl alkylaminen Berichte der Deutschen Chemischen Gesellschaft A and B Series 58 9 2042 6 doi 10 1002 cber 19250580917 Templeman W G Marmoy C J 2008 The effect upon the growth of plants of watering with solutions of plant growth substances and of seed dressings containing these materials Annals of Applied Biology 27 4 453 471 doi 10 1111 j 1744 7348 1940 tb07517 x Pokorny Robert 1941 New Compounds Some Chlorophenoxyacetic Acids J Am Chem Soc 63 6 1768 doi 10 1021 ja01851a601 PGR Planofix Crop Science India www cropscience bayer in Retrieved 2022 04 28 1H Indole 3 acetic acid Registry of Toxic Effects of Chemical Substances RTECS Page last updated November 8 2017 Indole 3 Acetic Acid Material Safety Data Sheet November 2008 Miller Charles A 1997 12 26 Expression of the Human Aryl Hydrocarbon Receptor Complex in Yeast ACTIVATION OF TRANSCRIPTION BY INDOLE COMPOUNDS Journal of Biological Chemistry 272 52 32824 32829 doi 10 1074 jbc 272 52 32824 ISSN 1083 351X PMID 9407059 S2CID 45619222 Retrieved 2020 01 08 Ji Yun Gao Yuan Chen Hong Yin Yue Zhang Weizhen 2019 09 03 Indole 3 Acetic Acid Alleviates Nonalcoholic Fatty Liver Disease in Mice via Attenuation of Hepatic Lipogenesis and Oxidative and Inflammatory Stress Nutrients 11 9 2062 doi 10 3390 nu11092062 ISSN 2072 6643 PMC 6769627 PMID 31484323 Dou Laetitia Sallee Marion Cerini Claire Poitevin Stephane Gondouin Bertrand Jourde Chiche Noemie Fallague Karim Brunet Philippe Calaf Raymond Dussol Bertrand Mallet Bernard Dignat George Francoise Burtey Stephane April 2015 The cardiovascular effect of the uremic solute indole 3 acetic acid Journal of the American Society of Nephrology 26 4 876 887 doi 10 1681 ASN 2013121283 ISSN 1533 3450 PMC 4378098 PMID 25145928 Lai Yunjia Liu Chih Wei Yang Yifei Hsiao Yun Chung Ru Hongyu Lu Kun 2021 High coverage metabolomics uncovers microbiota driven biochemical landscape of interorgan transport and gut brain communication in mice Nature Communications 12 6000 6000 Bibcode 2021NatCo 12 6000L doi 10 1038 s41467 021 26209 8 PMC 8526691 PMID 34667167 Furukawa Satoshi Usuda Koji Abe Masayoshi Ogawa Izumi 2005 Effect of Indole 3 Acetic Acid Derivatives on Neuroepithelium in Rat Embryos The Journal of Toxicological Sciences 30 3 165 74 doi 10 2131 jts 30 165 PMID 16141651 a b Jeong YM Oh MH Kim SY Li H Yun HY Baek KJ Kwon NS Kim WY Kim DS 2010 Indole 3 acetic acid horseradish peroxidase induces apoptosis in TCCSUP human urinary bladder carcinoma cells Pharmazie 65 2 122 6 PMID 20225657 Wardman P 2002 Indole 3 acetic acids and horseradish peroxidase a new prodrug enzyme combination for targeted cancer therapy Curr Pharm Des 8 15 1363 74 doi 10 2174 1381612023394610 PMID 12052213 Dalmazzo LF Santana Lemos BA Jacomo RH Garcia AB Rego EM da Fonseca LM Falcao RP 2011 Antibody targeted horseradish peroxidase associated with indole 3 acetic acid induces apoptosis in vitro in hematological malignancies Leuk Res 35 5 657 62 doi 10 1016 j leukres 2010 11 025 PMID 21168913 S2CID 32655907 cited in Wayne AS Fitzgerald DJ Kreitman RJ Pastan I 2014 Immunotoxins for leukemia Blood 123 16 2470 7 doi 10 1182 blood 2014 01 492256 PMC 3990911 PMID 24578503 Retrieved from https en wikipedia org w index php title Indole 3 acetic acid amp oldid 1184550647, wikipedia, wiki, book, books, library,

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