Shaping Small Bioactive Molecules to Untangle Their Biological Function: A Focus on Fluorescent Plant Hormones  Beatrice Lace, Cristina Prandi  Molecular.

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Shaping Small Bioactive Molecules to Untangle Their Biological Function: A Focus on Fluorescent Plant Hormones  Beatrice Lace, Cristina Prandi  Molecular Plant  Volume 9, Issue 8, Pages 1099-1118 (August 2016) DOI: 10.1016/j.molp.2016.06.011 Copyright © 2016 The Author Terms and Conditions

Figure 1 Plot of Wavelength (nm) of Maximum Absorption (λex, Left) and Emission (λem, Right) for Selected Fluorophores. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 2 Molecular Structure of Xanthene, and the Most Common Fluorescein and Rhodamine Commercial Dyes. Asterisk indicates variable functional groups, i.e., amine-reactive succinimidyl ester, thiol, aldehyde, and carboxylic acid reactive forms. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 3 Use of Fluorescein as Fluorogenic Probe and Variation of Absorption/Emission Properties of Fluorescein Depending on pH (from Margulies et al., 2005). Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 4 Molecular Structure of Alexa Fluor Dye Series. Asterisks indicate variable functional groups, i.e., amine-reactive succinimidyl ester, thiol, aldehyde, and carboxylic acid reactive forms. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 5 Molecular Structure of a 7-Substituted Coumarin Derivative, Coumarin 343, and Non-fluorescent NBD-Cl. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 6 Molecular Structure of s-Indacene, BODIPY Core, Aza-BODIPY, and a Selection of Commercially Available BODIPYs. Asterisks indicate variable functional groups, i.e., amine-reactive succinimidyl ester, thiol, aldehyde, and carboxylic acid reactive forms. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 7 Molecular Structure of the Natural Auxin IAA and Its Fluorescent Conjugates IAA-FITC and IAA-RITC. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 8 Molecular Structure of Fluorescence-Tagged Auxins NBD-IAA and NBD-NAA. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 9 Molecular Structure of Gibberellins and Their Fluorescence-Tagged Derivatives GA4-Fl and GA3-Fl. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 10 Molecular Structure of a Natural Brassinosteroid and the Fluorescence-Labeled Brassinosteroid Analog AFCS. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 11 Molecular Structure of (−)-Jasmonic Acid and Its Bioactive Fluorescent Derivative. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 12 Molecular Structure of Abscisic Acid, the Cytokinin trans-Zeatin, and Their Fluorescent Derivatives. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 13 General Structure of SLs with Ring Lettering, Strigol-like and Orobanchol-like Families, Selection of Natural SLs, and Carlactone. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 14 Molecular Structure of Synthetic SLs. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 15 Hydrolysis of Strigolactones Leads to Generation of Two Fragments, the Formyl Tricyclic ABC Core and the Hydroxybutenolide. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 16 Molecular Structure of Functionalized SL Analogs. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 17 Molecular Structure of Fluorescent SL Derivatives. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 18 The Structure of BODIPY Derivatives Used to Map the Distribution of SLs in Arabidopsis Root System. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 19 Illustration of the Molecular Design of Fluorescence Turn-On Molecule YLG for D14-like Strigolactone Receptors and Molecular Structure of the Fluorogenic Probe Bearing Two D Rings (YLGW). Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions

Figure 20 Fluorescent Labeling of Plant Hormones Represented in Its Different Interconnected Phases Involving Both Chemistry and Biology. Molecular Plant 2016 9, 1099-1118DOI: (10.1016/j.molp.2016.06.011) Copyright © 2016 The Author Terms and Conditions