Pyrabactin
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| Names | |
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| Preferred IUPAC name
4-Bromo-N-[(pyridin-2-yl)methyl]naphthalene-1-sulfonamide | |
| Other names
4-Bromo-N-(pyridin-2-ylmethyl)naphthalene-1-sulfonamide
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.212.933 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C16H13BrN2O2S | |
| Molar mass | 377.26 g·mol−1 |
| Appearance | White to off-white powder[1] |
| Solubility in DMSO | >10 mg/mL[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pyrabactin is a synthetic sulfonamide that mimics abscisic acid (ABA), a naturally produced stress hormone in plants that helps them cope with drought conditions by inhibiting growth. ABA can be manufactured for agricultural use; however, ABA is light-sensitive and costly to make. Pyrabactin is relatively inexpensive, easy to make, and not sensitive to light. Unlike ABA, pyrabactin activates only a few of the 14 ABA receptors in the plant needed for effective drought tolerance.[2] Its role as an ABA mimic may make pyrabactin an important tool for protecting crops against drought and cold weather.[3][4]
The discovery of pyrabactin by Sean Cutler was named a breakthrough research of 2009 by Science magazine.[5]
Pyrabactin (for pyridyl containing ABA activator) is a naphthalene sulfonamide hypocotyl cell expansion inhibitor. A combination of genetic, transcriptomic and physiological evidence demonstrated that pyrabactin activates the ABA pathway in a manner very similar to ABA[6]. As such, pyrabactin is the first ABA agonist that is not an ABA analog and may ultimately lead to the development of a new family of synthetic plant growth regulators.
References
- ^ a b Pyrabactin, Sigma-Aldrich
- ^ Organic compound comes to the aid of thirsty plants, Royal Society of Chemistry, 1 May 2009
- ^ Pyrabactin – American Chemical Society
- ^ Synthetic chemical offers solution for crops facing drought
- ^ Growing drought-tolerant crops inching forward (Science Blog)
- ^ Melcher, Karsten; Xu, Yong; Ng, Ley-Moy; Zhou, X Edward; Soon, Fen-Fen; Chinnusamy, Viswanathan; Suino-Powell, Kelly M; Kovach, Amanda; Tham, Fook S; Cutler, Sean R; Li, Jun; Yong, Eu-Leong; Zhu, Jian-Kang; Xu, H Eric (September 2010). "Identification and mechanism of ABA receptor antagonism". Nature Structural & Molecular Biology. 17 (9): 1102–1108. doi:10.1038/nsmb.1887. ISSN 1545-9993. PMC 2933329. PMID 20729862.