PI-55
(Synonyms: 6-(2-羟基-3-甲基苄氨基)嘌呤) 目录号 : GC63299
PI-55 是特异性 cytokinin receptor 抑制剂。PI-55 在结构上与 6-benzylaminopurine (BAP) 相关，并被证明能竞争性地抑制 BAP 与拟南芥特异性受体 CRE1/AHK4 和 AHK3 的结合。PI-55 抑制细胞分裂素诱导吸器形成和寄生虫侵袭性增加。
Cas No.:1122579-42-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >98.00%
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PI-55 is a specific cytokinin receptor inhibitor. PI-55 is structurally related to 6-benzylaminopurine (BAP) and was shown to inhibit competitively BAP binding on Arabidopsis-specific receptors CRE1/AHK4 and AHK3. PI-55 inhibits cytokinins induced haustorium formation and increased parasite aggressiveness[1].
PI-55 at high concentrations (10 μM and 100 μM), which causes an incomplete blocking of early haustorial structure development, especially when cytokinin activity promotes it. PI-55 treatment also reduces the overall aggressiveness of P. ramosa when applied with BAP in comparison with BAP alone, suggesting that the signaling pathway leading to early haustorial structure formation involves histidine kinase receptors homologous to CRE1/AHK4 and AHK3[1].
[1]. Goyet V, et al. Haustorium initiation in the obligate parasitic plant Phelipanche ramosa involves a host-exudated cytokinin signal. J Exp Bot. 2017;68(20):5539-5552.
| Cas No. | 1122579-42-3 | SDF | |
| 别名 | 6-(2-羟基-3-甲基苄氨基)嘌呤 | ||
| 分子式 | C13H13N5O | 分子量 | 255.28 |
| 溶解度 | 储存条件 | Store at -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.9173 mL | 19.5863 mL | 39.1727 mL |
| 5 mM | 0.7835 mL | 3.9173 mL | 7.8345 mL |
| 10 mM | 0.3917 mL | 1.9586 mL | 3.9173 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The purine derivative PI-55 blocks cytokinin action via receptor inhibition
FEBS J 2009 Jan;276(1):244-53.PMID:19032596DOI:10.1111/j.1742-4658.2008.06777.x.
One of several potential approaches to study mechanisms of action of biologically active compounds is to develop their agonists and antagonists. In the present study, we report the identification of the first known molecule antagonizing the activity of the plant hormone cytokinin at the receptor level. This compound, 6-(2-hydroxy-3-methylbenzylamino)purine, designated PI-55 in the present study, is structurally closely related to cytokinin 6-benzylaminopurine, but substitutions at specific positions of the aromatic side chain strongly diminished its cytokinin activity and conferred antagonistic properties. PI-55 competitively inhibited the binding of the natural ligand trans-zeatin to the Arabidopsis cytokinin receptors cytokinin response 1 (CRE1)/Arabidopsis histidine kinase (AHK) 4 and AHK3 and repressed induction of the cytokinin response gene ARR5:GUS. Genetic analysis revealed that CRE1/AHK4 is the primary target of PI-55. Cytokinin bioassays also demonstrated the anticytokinin effect of PI-55 in several other species. Furthermore, we show that PI-55 accelerated the germination of Arabidopsis seeds and promoted the root growth and formation of lateral roots, thus phenocopying the known consequences of a lowered cytokinin status and demonstrating its potential to inhibit cytokinin perception in planta. PI-55 is the first example for the targeted development of a cytokinin antagonist and represents an initial step for the preparation of cytokinin antagonists with broad activity and reduced agonistic properties.
Dissecting the role of two cytokinin analogues (INCYDE and PI-55) on in vitro organogenesis, phytohormone accumulation, phytochemical content and antioxidant activity
Plant Sci 2015 Sep;238:81-94.PMID:26259177DOI:10.1016/j.plantsci.2015.05.018.
There is a continuous search for new chemical entities to expand the collection of suitable compounds to increase the efficiency of micropropagation protocols. Two cytokinin (CK) analogues, 2-chloro-6-(3-methoxyphenyl)aminopurine (INCYDE) and CK antagonist 6-(2-hydroxy-3-methylbenzylamino)purine (PI-55) were used as a tool to elucidate the auxin-CK crosstalk under in vitro conditions in the medicinally important plant, Eucomis autumnalis subspecies autumnalis. These compounds were tested at 0.01, 0.1 and 10 μM alone as well as in combination with benzyladenine (BA) and naphthaleneacetic acid (NAA). The organogenesis, phytohormone content, phytochemical and antioxidant response in 10 week-old-in vitro regenerated E. autumnalis subspecies autumnalis was evaluated. INCYDE generally favoured shoot regeneration while the effect of PI-55 was more evident in root proliferation. Overall, INCYDE promoted the accumulation of higher concentrations and varieties of endogenous CK relative to the PI-55 treatments. In contrast, higher concentration of indole-3-acetic acid and 2-oxindole-3-acetic acid were generally observed in PI-55-supplemented cultures when compared to plantlets derived from INCYDE. Both CK analogues (individually and in-conjunction with exogenously applied PGRs) significantly influenced the phytochemicals and consequently the antioxidant potential of the in vitro regenerants. These results provided insight on how to alleviate root inhibition, a problem which causes considerable loss of several elite species during micropropagation.
Cytokinin receptor antagonists derived from 6-benzylaminopurine
Phytochemistry 2010 May;71(7):823-30.PMID:20189204DOI:10.1016/j.phytochem.2010.01.018.
Recently we reported 6-(2-hydroxy-3-methylbenzylamino)purine (PI-55) as the first molecule to antagonize cytokinin activity at the receptor level. Here we report the synthesis and in vitro biological testing of eleven BAP derivatives substituted in the benzyl ring and in the C2, N7 and N9 positions of the purine moiety. The ability of the compounds to interact with Arabidopsis cytokinin receptors AHK3 and CRE1/AHK4 was tested in bacterial receptor and in live-cell binding assays, and in an Arabidopsis ARR5:GUS (Arabidopsis response regulator 5) reporter gene assay. Cytokinin activity of the compounds was determined in classical cytokinin biotests (tobacco callus, wheat leaf senescence and Amaranthus bioassays). 6-(2,5-Dihydroxybenzylamino)purine (LGR-991) was identified as a cytokinin receptor antagonist. At the molecular level LGR-991 blocks the cytokinin receptor CRE1/AHK4 with the same potency as PI-55. Moreover, LGR-991 acts as a competitive inhibitor of AHK3, and importantly shows reduced agonistic effects in comparison to PI-55 in the ARR5:GUS reporter gene assay and in cytokinin bioassays. LGR-991 causes more rapid germination of Arabidopsis seeds and increases hypocotyl length of dark-grown seedlings, which are characteristics of plants with a reduced cytokinin status. LGR-991 exhibits a structural motive that might lead to preparation of cytokinin antagonists with a broader specificity and reduced agonistic properties.
A Stimulatory Role for Cytokinin in the Arbuscular Mycorrhizal Symbiosis of Pea
Front Plant Sci 2019 Mar 12;10:262.PMID:30915091DOI:10.3389/fpls.2019.00262.
The arbuscular mycorrhizal (AM) symbiosis between terrestrial plants and AM fungi is regulated by plant hormones. For most of these, a role has been clearly assigned in this mutualistic interaction; however, there are still contradictory reports for cytokinin (CK). Here, pea plants, the wild type (WT) cv. Sparkle and its mutant E151 (Pssym15), were inoculated with the AM fungus Rhizophagus irregularis. E151 has previously been characterized as possessing high CK levels in non-mycorrhizal (myc-) roots and exhibiting high number of fungal structures in mycorrhizal (myc+) roots. Myc- and myc+ plants were treated 7, 9, and 11 days after inoculation (DAI) with synthetic compounds known to alter CK status. WT plants were treated with a synthetic CK [6-benzylaminopurine (BAP)] or the CK degradation inhibitor INCYDE, whereas E151 plants were treated with the CK receptor antagonist PI-55. At 13 DAI, plant CK content was analyzed by mass spectrometry. The effects of the synthetic compounds on AM colonization were assessed at 28 (WT) or 35 (E151) DAI via a modified magnified intersections method. The only noticeable difference seen between myc- and myc+ plants in terms of CK content was in the levels of nucleotides (NTs). Whereas WT plants responded to fungi by lowering their NT levels, E151 plants did not. Since NTs are thought to be converted into active CK forms, this result suggests that active CKs were synthesized more effectively in WT than in E151. In general, myc+ and myc- WT plants responded similarly to INCYDE by lowering significantly their NT levels and increasing slightly their active CK levels; these responses were less obvious in BAP-treated WT plants. In contrast, the response of E151 plants to PI-55 depended on the plant mycorrhizal status. Whereas treated myc- plants exhibited high NT and low active CK levels, treated myc+ plants displayed low levels of both NTs and active CKs. Moreover, treated WT plants were more colonized than treated E151 plants. We concluded that CKs have a stimulatory role in AM colonization because increased active CK levels were paralleled with increased AM colonization while decreased CK levels corresponded to reduced AM colonization.
The Role of a Cytokinin Antagonist in the Progression of Clubroot Disease
Biomolecules 2023 Feb 5;13(2):299.PMID:36830668DOI:10.3390/biom13020299.
Plasmodiophora brassicae is an obligate biotrophic pathogen causing clubroot disease in cruciferous plants. Infected plant organs are subject to profound morphological changes, the roots form characteristic galls, and the leaves are chlorotic and abscise. The process of gall formation is governed by timely changes in the levels of endogenous plant hormones that occur throughout the entire life cycle of the clubroot pathogen. The homeostasis of two plant hormones, cytokinin and auxin, appears to be crucial for club development. To investigate the role of cytokinin and auxin in gall formation, we used metabolomic and transcriptomic profiling of Arabidopsis thaliana infected with clubroot, focusing on the late stages of the disease, where symptoms were more pronounced. Loss-of-function mutants of three cytokinin receptors, AHK2, AHK3, and CRE1/AHK4, were employed to further study the homeostasis of cytokinin in response to disease progression; ahk double mutants developed characteristic symptoms of the disease, albeit with varying intensity. The most susceptible to clubroot disease was the ahk3 ahk4 double mutant, as revealed by measuring its photosynthetic performance. Quantification of phytohormone levels and pharmacological treatment with the cytokinin antagonist PI-55 showed significant changes in the levels of endogenous cytokinin and auxin, which was manifested by both enhanced and reduced development of disease symptoms in different genotypes.