1109241-72-6
Chemical Structure
trans-AzoTAB
- CAS. Nr.: 1109241-72-6
- Formula:C19H26BrN3O2
- Molecular Weight:408.33
IUPAC Name: (E)-2-(4-((4-ethoxyphenyl)diazenyl)phenoxy)-N,N,N-trimethylethan-1-aminium bromide
InChIKey: VJBFCBWAMWOCHY-ANVLNOONSA-M
SMILES: CCOC1=CC=C(/N=N/C2=CC=C(OCC[N+](C)(C)C)C=C2)C=C1.[Br-]
Biological Activity: trans-AzoTAB is a photoresponsive potassium/sodium/calcium channel modulator and DNA-binding agent. trans-AzoTAB undergoes trans-cis isomerization driven by light, with variable polarity and DNA affinity. trans-AzoTAB also enhances voltage-gated potassium currents and inhibits sodium and calcium currents in cardiomyocytes, thereby reducing spontaneous electrical activity and excitation conduction velocity. In addition, trans-AzoTAB induces compaction and frozen conformation of λ-phage DNA, and non-sequence-dependently inhibits transcription and translation processes in the dark; its activity can be reversed and restored by visible light after activation with ultraviolet irradiation. trans-AzoTAB can serve as a probe for two-photon optical regulation of myocardial excitability, and is used to construct photoresponsive interfacial polymer structures[1][2][3][4].
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trans-AzoTAB | 96.01% | trans-AzoTAB is a photoresponsive potassium/sodium/calcium channel modulator and DNA-binding agent. trans-AzoTAB undergoes trans-cis isomerization driven by light, with variable polarity and DNA affinity. trans-AzoTAB also enhances voltage-gated potassium currents and inhibits sodium and calcium currents in cardiomyocytes, thereby reducing spontaneous electrical activity and excitation conduction velocity. In addition, trans-AzoTAB induces compaction and frozen conformation of λ-phage DNA, and non-sequence-dependently inhibits transcription and translation processes in the dark; its activity can be reversed and restored by visible light after activation with ultraviolet irradiation. trans-AzoTAB can serve as a probe for two-photon optical regulation of myocardial excitability, and is used to construct photoresponsive interfacial polymer structures. | ||||||||||||||||||||
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- [1]. Frolova SR, et al. Photocontrol of Voltage-Gated Ion Channel Activity by Azobenzene Trimethylammonium Bromide in Neonatal Rat Cardiomyocytes. PLoS One. 2016;11(3):e0152018. Published 2016 Mar 25. [Content Brief]
- [2]. Sun Y L, et al. Photocontrol of end-grafted lambda-phage DNA[J]. Soft Matter, 2011, 7(12): 5578-5584.
- [3]. Estévez-Torres A, et al. Sequence-independent and reversible photocontrol of transcription/expression systems using a photosensitive nucleic acid binder. Proc Natl Acad Sci U S A. 2009;106(30):12219-12223. [Content Brief]
- [4]. Shcherbakov D, et al. Optical control of cardiac cell excitability based on two-photon infrared absorption of AzoTAB[J]. arXiv preprint arXiv:1401.0346, 2014.
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