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

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

1 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 (August 2016) DOI: /j.molp Copyright © 2016 The Author Terms and Conditions

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

3 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, DOI: ( /j.molp ) Copyright © 2016 The Author Terms and Conditions

4 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, DOI: ( /j.molp ) Copyright © 2016 The Author Terms and Conditions

5 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, DOI: ( /j.molp ) Copyright © 2016 The Author Terms and Conditions

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

7 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, DOI: ( /j.molp ) Copyright © 2016 The Author Terms and Conditions

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

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

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

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

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

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

14 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, DOI: ( /j.molp ) Copyright © 2016 The Author Terms and Conditions

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

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

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

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

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

20 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, DOI: ( /j.molp ) Copyright © 2016 The Author Terms and Conditions

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


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