Piperonyl butoxide
(Synonyms: 增效醚; ENT-14250) 目录号 : GC61190
An insecticide synergist
Cas No.:51-03-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Piperonyl butoxide is a synergist used to enhance the activity of insecticides, including pyrethrin insecticides, through inhibition of cytochrome P450 enzymes (CYPs).1,2 It increases the toxicity of the pyrethroid insecticide deltamethrin to field-collected, deltamethrin-resistant strains of the bed bug C. lectularius by 40- to 176-fold when used at a concentration of 50 μg/μL.2 Piperonyl butoxide also increases the toxicity of the organotin insecticide Plictran to fourth instar larvae of susceptible strains of the cotton leafworm S. littoralis (LD50s = 0.78 and 40 μg/larva with and without piperonyl butoxide, respectively), as well as field strains (LD50s = 0.015 and 1.1 μg/larva with and without piperonyl butoxide, respectively).3 It is not toxic to the freshwater invertebrates H. azteca, C. tentans, and L. variegatus (LC50s = 530, 2,740, and 3,540 μg/L, respectively) and reduces the toxicity of the organophosphate pesticides diazinon , chlorpyrifos , and azinphos-methyl, which require activation by CYP enzymes in these organisms.1 Formulations containing piperonyl butoxide have been used for the control of agricultural, household, and veterinary pests.
1.Ankley, G.T., and Collyard, S.A.Influence of piperonyl butoxide on the toxicity of organophosphate insecticides to three species of freshwater benthic invertebratesComp. Biochem. Physiol.110(2)149-155(1995) 2.Romero, A., Potter, M.F., and Haynes, K.F.Evaluation of piperonyl butoxide as a deltamethrin synergist for pyrethroid-resistant bed bugsJ. Econ. Entomol.102(6)2310-2315(2009) 3.Radwan, H.S.A., Riskallah, M.R., and El-Keie, I.A.Synergistic effects on the toxicity of organotins on cotton leafwormsToxicology14(3)193-198(1979)
| Cas No. | 51-03-6 | SDF | |
| 别名 | 增效醚; ENT-14250 | ||
| Canonical SMILES | CCCC1=C(COCCOCCOCCCC)C=C2OCOC2=C1 | ||
| 分子式 | C19H30O5 | 分子量 | 338.44 |
| 溶解度 | Ethanol: 100 mg/mL (295.47 mM); DMSO: 100 mg/mL (295.47 mM); Water: < 0.1 mg/mL (insoluble) | 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 | 2.9547 mL | 14.7737 mL | 29.5473 mL |
| 5 mM | 0.5909 mL | 2.9547 mL | 5.9095 mL |
| 10 mM | 0.2955 mL | 1.4774 mL | 2.9547 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 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
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。
Examining the developmental toxicity of Piperonyl butoxide as a Sonic hedgehog pathway inhibitor
Chemosphere 2021 Feb;264(Pt 1):128414.PMID:33007564DOI:10.1016/j.chemosphere.2020.128414.
Piperonyl butoxide (PBO) is a semisynthetic chemical present in hundreds of pesticide formulations used in agricultural, commercial, and residential settings. PBO acts as a pesticide synergist by inhibiting insect cytochrome P450 enzymes and is often present at much higher concentrations than active insecticidal ingredients. PBO was recently discovered to also inhibit Sonic hedgehog (Shh) signaling, a key molecular pathway in embryonic development and in brain and face morphogenesis. Recent animal model studies have shown that in utero PBO exposure can cause overt craniofacial malformations or more subtle neurodevelopmental abnormalities. Related adverse developmental outcomes in humans are etiologically heterogeneous, and, while studies are limited, PBO exposure during pregnancy has been linked to neurodevelopmental deficits. Contextualized in PBO's newly recognized mechanism as a Shh signaling inhibitor, these findings support more rigorous examination of the developmental toxicity of PBO and its potential contribution to etiologically complex human birth defects. In this review, we highlight environmental sources of human PBO exposure and summarize existing animal studies examining the developmental impact of prenatal PBO exposure. Also presented are critical knowledge gaps in our understanding of PBO's pharmacokinetics and potential role in gene-environment and environment-environment interactions that should be addressed to better understand the human health impact of environmental PBO exposure.
Effects of Piperonyl butoxide on the Accumulation of Lipid and the Transcript Levels of DtMFPα in Dunaliella tertiolecta
J Agric Food Chem 2022 Sep 28;70(38):12074-12084.PMID:36122177DOI:10.1021/acs.jafc.2c03006.
As one of the sources of biodiesel, microalgae are expected to solve petroleum shortage. In this study, different concentrations of Piperonyl butoxide were added to the culture medium to investigate their effects on the growth, pigment content, lipid accumulation, and content of carotenoids in Dunaliella tertiolecta. The results showed that Piperonyl butoxide addition significantly decreased the biomass, chlorophyll content, and total carotenoid content but hugely increased the lipid accumulation. With the treatment of 150 ppm Piperonyl butoxide combined with 8000 Lux light intensity, the final lipid accumulation and single-cell lipid content were further increased by 21.79 and 76.42% compared to those of the control, respectively. The lipid accumulation in D. tertiolecta is probably related to the increased expression of DtMFPα in D. tertiolecta under the action of Piperonyl butoxide. The phylogenetic trees of D. tertiolecta and other oil-rich plants were constructed by multiple sequence alignment of DtMFPα, demonstrating their evolutionary relationship, and the tertiary structure of DtMFPα was predicted. In conclusion, Piperonyl butoxide has a significant effect on lipid accumulation in D. tertiolecta, which provides valuable insights into chemical inducers to enhance biodiesel production in microalgae to solve the problem of diesel shortage.
Piperonyl butoxide, a synergist of pesticides can elicit male-mediated reproductive toxicity
Reprod Toxicol 2021 Mar;100:120-125.PMID:33515694DOI:10.1016/j.reprotox.2021.01.010.
A semi-synthetic methylenedioxyphenyl compound Piperonyl butoxide (PBO) has been used as a ubiquitous synergist to increase the insecticidal effect of pesticides for agricultural and household use. Despite previously demonstrated effects of PBO, the detailed mechanism of PBO in spermatozoa and reproductive toxic effects on male germ cells have not been fully elucidated. Therefore, this study evaluated the effects of PBO on various sperm functions during capacitation and clarified the mechanisms of reproductive toxic effects on male fertility at different concentrations of PBO (0.1, 1, 10, and 100 μM). Sperm motility and kinematics were assessed using computer-assisted sperm analysis and the status of capacitation was evaluated using combined H33258/chlortetracycline (CTC) staining. Intracellular adenosine triphosphate (ATP) and cell viability levels were also measured. In addition, protein kinase A (PKA) activity and protein tyrosine phosphorylation were evaluated. In addition, in vitro fertilization was performed to determine the effects of PBO on cleavage and blastocyst formation rates. We found that PBO significantly decreased sperm motility, kinematics, and acrosome-reacted and capacitated spermatozoa. In addition, PBO suppressed the intracellular ATP levels and directly affected cell viability. Moreover, PBO detrimentally decreased the activation of PKA and altered the levels of tyrosine-phosphorylated proteins. Consequently, cleavage and blastocyst formation rates were significantly reduced in a dose-dependent manner. In line with our observations, the synergist of pesticides PBO may directly and/or indirectly cause disorder in male fertility. Hence, we suggest that careful attention is made to consider reproductive toxicity when using PBO as a synergist.
Emerging Mosquito Resistance to Piperonyl Butoxide-Synergized Pyrethroid Insecticide and Its Mechanism
J Med Entomol 2022 Mar 16;59(2):638-647.PMID:35050361DOI:10.1093/jme/tjab231.
Piperonyl butoxide (PBO)-synergized pyrethroid products are widely available for the control of pyrethroid-resistant mosquitoes. To date, no study has examined mosquito resistance after pre-exposure to PBO and subsequent enzymatic activity when exposed to PBO-synergized insecticides. We used Culex quinquefasciatus Say (Diptera: Culicidae), an important vector of arboviruses and lymphatic filariasis, as a model to examine the insecticide resistance mechanisms of mosquitoes to PBO-synergized pyrethroid using modified World Health Organization tube bioassays and biochemical analysis of metabolic enzyme expressions pre- and post-PBO exposure. Mosquito eggs and larvae were collected from three cities in Orange County in July 2020 and reared in insectary, and F0 adults were used in this study. A JHB susceptible strain was used as a control. Mosquito mortalities and metabolic enzyme expressions were examined in mosquitoes with/without pre-exposure to different PBO concentrations and exposure durations. Except for malathion, wild strain Cx quinquefasciatus mosquitoes were resistant to all insecticides tested, including PBO-synergized pyrethroids (mortality range 3.7 ± 4.7% to 66.7 ± 7.7%). Wild strain mosquitoes had elevated levels of carboxylesterase (COE, 3.8-fold) and monooxygenase (P450, 2.1-fold) but not glutathione S-transferase (GST) compared to susceptible mosquitoes. When wild strain mosquitoes were pre-exposed to 4% PBO, the 50% lethal concentration of deltamethrin was reduced from 0.22% to 0.10%, compared to 0.02% for a susceptible strain. The knockdown resistance gene mutation (L1014F) rate was 62% in wild strain mosquitoes. PBO pre-exposure suppressed P450 enzyme expression levels by 25~34% and GST by 11%, but had no impact on COE enzyme expression. Even with an optimal PBO concentration (7%) and exposure duration (3h), wild strain mosquitoes had significantly higher P450 enzyme expression levels after PBO exposure compared to the susceptible laboratory strain. These results further demonstrate other studies that PBO alone may not be enough to control highly pyrethroid-resistant mosquitoes due to multiple resistance mechanisms. Mosquito resistance to PBO-synergized insecticide should be closely monitored through a routine resistance management program for effective control of mosquitoes and the pathogens they transmit.
Piperonyl butoxide activates c-Jun and ATF-2 in the hepatocytes of mice
Arch Toxicol 2008 Oct;82(10):749-53.PMID:18228000DOI:10.1007/s00204-008-0283-0.
In order to clarify the possible mechanism of hepatocarcinogenesis induced by Piperonyl butoxide, we attempted to identify the transcription factor activated by Piperonyl butoxide in the male ICR mouse liver. Administration of 0.6% Piperonyl butoxide for 24 h elevated the level of liver nuclear proteins that bind to an AP-1 consensus oligonucleotide, and these proteins demonstrated a supershift with the anti-c-Jun antibody. Additionally, immunoblot analysis revealed that Piperonyl butoxide induced c-Jun phosphorylation within 8 h of administration, and phosphorylated ATF-2 was detected after 24 h of Piperonyl butoxide treatment. Immunohistochemical analysis also demonstrated the presence of phosphorylated ATF-2 in the hepatocyte nuclei of mice fed with 0.6% Piperonyl butoxide for 24 h. Furthermore, Piperonyl butoxide induced ATF-2 phosphorylation in TLR-3, a mouse immortalized hepatocyte cell line. These results indicated that Piperonyl butoxide activated c-Jun and ATF-2 in mouse hepatocytes during the early stage of hepatocarcinogenesis.