Synthesis and Characterization of the 7-(4-Aminomethyl-1<i>H</i>-1,2,3-triazol-1-yl) Analogue of Kabiramide C

Petchprayoon, Chutima; Suwanborirux, Khanit; Miller, Reagan L.; Sakata, Taizo; Marriott, Gerard

doi:10.1021/np049670z

Cited by 20 publications

(25 citation statements)

References 18 publications

(24 reference statements)

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“…The reaction mixture was stirred at room temperature in the dark under N 2 atmosphere. After 8 h, the mixture was concentrated and isolated by silica gel TLC (CH 2 Cl 2 / MeOH ) 20:3) and C 18 G-Actin. G-actin was prepared from rabbit skeletal muscle using a standard protocol developed in the principal investigator's laboratory (16).…”

Section: Methodsmentioning

confidence: 99%

“…After considering several different approaches for the preparation of C-7-directed optical probes, we elected to synthesize the key intermediate, 7-(4-aminomethyl-1H-1,2,3-triazol-1-yl)-kabiramide C (AMT-KabC) from KabC (18). The long linker between the C-7 of KabC and the optical probe minimizes effects of the bulky probe on actin binding.…”

Section: Design Of Fluorescent Kabc Probesmentioning

confidence: 99%

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Fluorescent Kabiramides: New Probes to Quantify Actin in Vitro and in Vivo

et al. 2005

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We present the design, synthesis, and biochemical and spectroscopic characterization of five functional fluorescent conjugates of kabiramide C (KabC), a small molecule biomimetic of gelsolin. The tetramethylrhodamine (TMR), rhodol green (RG), IC5, dapoxyl (DAP), and fluorescein diester (FDE) conjugates of KabC bind specifically to actin at the barbed end in a 1:1 complex. These probes are shown to function in an indistinguishable manner to the unmodified KabC. Various modalities of the fluorescence emission of these KabC probes, including fluorescence anisotropy and fluorescence resonance energy transfer, are used for the development of assays for the rapid determination of G-actin concentration in solution. The TMR-KabC and FDE-KabC probes are cell permeable and provide unique imaging information on the distribution and dynamics of actin filament within living cells.

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Section: Methodsmentioning

confidence: 99%

Section: Design Of Fluorescent Kabc Probesmentioning

confidence: 99%

Fluorescent Kabiramides: New Probes to Quantify Actin in Vitro and in Vivo

et al. 2005

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“…Alternatively, these partial compounds may have been degraded in the course of the experiments. Synthesis of a 7-(4-aminomethyl-1H-1,2,3-triazol-1-yl) analogue of CYCLE [27] would allow the generation of an optical probe to test these possibilities.…”

Section: Discussionmentioning

confidence: 99%

Effects of ulapualide A and synthetic macrolide analogues on actin dynamics and gene regulation

Vincent

Saxton

Baker-Glenn

et al. 2007

Cell. Mol. Life Sci.

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Several marine macrolide toxins act as potent and specific actin-severing molecules. Recent elucidation of their stereochemistries and modes of interaction with actin has allowed the syntheses of bioactive analogues. Here we used synthetic analogues in a structure-function analysis of ulapualide A, a trisoxazole-based macrolide. Ulapualide A harboured potent actin-depolymerising activity both in cells and in vitro. Its synthetic diastereoisomer was three orders of magnitude less active than the natural toxin and synthetic macrolide fragments lacked actin-capping/ severing activity altogether. Modulation of serum response factor (SRF)-dependent gene expression, as described for other actin-binding toxins, was also examined. Specific changes in response to ulapualide A were not observed, primarily due to its profound effects on cytoskeletal integrity and cell adhesion. Several synthetic fragments of ulapualide A also had no effect on SRF-dependent gene expression. However, inhibition was observed with a molecule corresponding to the extended aliphatic side chain of halichondramide, a structurally related macrolide. These findings indicate that side-chain derivatives of trisoxazole-based macrolides may serve to uncouple gene-regulatory events from actin dynamics.

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“…[49] The purities of the copper halide have a large influence on both reaction rate and completion of the reaction. [50][51][52][53] CuBr is most soluble in hydrolytic solvents, and recently the superior performance of CuBr in aqueous in vivo ligation has been demonstrated. [52,[54][55][56] Tornøe and Meldal [3] originally used CuI due to its partial solubility in solvents of intermediate polarity such as acetonitrile, THF, acetone, pyridine and DMSO and is particularly suited for anhydrous conditions.…”

Section: General Considerations In Cuaac Click Chemistry In Polymer Smentioning

confidence: 99%

Polymer “Clicking” by CuAAC Reactions

Meldal

2008

Macromol. Rapid Commun.

321

151

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The CuAAC “click” reaction has developed as one of the most useful and widely employed reactions in ligation within polymer chemistry. This is due to the unique properties of the Cu(I) catalysis which renders the reaction quantitative even at low concentrations, orthogonal with other chemistries and extremely robust. The formed triazole on the other hand is of intermediate polarity and chemically and biochemically “invisible”, and the CuAAC provides the ideal “click” reaction for stitching together polymer architectures of unprecedended complexity as was it molecular LEGO. The CuAAC “clicking” in polymer chemistry is increasing exponentially and lead to highly defined polymer materials with novel properties.magnified image

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Synthesis and Characterization of the 7-(4-Aminomethyl-1H-1,2,3-triazol-1-yl) Analogue of Kabiramide C

Cited by 20 publications

References 18 publications

Fluorescent Kabiramides: New Probes to Quantify Actin in Vitro and in Vivo

Fluorescent Kabiramides: New Probes to Quantify Actin in Vitro and in Vivo

Effects of ulapualide A and synthetic macrolide analogues on actin dynamics and gene regulation

Polymer “Clicking” by CuAAC Reactions

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