2. Metabolic Enzyme/Protease Stem Cell/Wnt Apoptosis
  3. Endogenous Metabolite YAP Glutathione Peroxidase Ferroptosis
  4. Pipecolic acid

Pipecolic acid is an orally bioavailable, blood-brain barrier-permeable metabolite of lysine with antioxidant, inhibitor, and inducer activity. Pipecolic acid modulates the YAP-GPX4 signaling pathway, reduces retinal vascular tube formation, and mitigates ferroptosis. Pipecolic acid potentiates voltage-sensitive Ca2+ channel currents and induces neuronal apoptosis. Pipecolic acid can be used for the research of diabetic retinopathy.

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Pipecolic acid

Pipecolic acid Chemical Structure

CAS No. : 535-75-1

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Solid + Solvent (Highly Recommended)
10 mM * 1 mL in Water
ready for reconstitution
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Based on 2 publication(s) in Google Scholar

Other Forms of Pipecolic acid:

Pipecolic acid Related Antibodies

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Human Endogenous Metabolite Microbial Metabolite

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YAP/TAZ YAP/TAZ-TEAD TEAD YAP1

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GPX1 GPX4

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Description

Pipecolic acid is an orally bioavailable, blood-brain barrier-permeable metabolite of lysine with antioxidant, inhibitor, and inducer activity. Pipecolic acid modulates the YAP-GPX4 signaling pathway, reduces retinal vascular tube formation, and mitigates ferroptosis. Pipecolic acid potentiates voltage-sensitive Ca2+ channel currents and induces neuronal apoptosis. Pipecolic acid can be used for the research of diabetic retinopathy[1][2].

IC50 & Target

Microbial Metabolite

 

Human Endogenous Metabolite

 

GPX4

 

In Vitro

Pipecolic acid mitigates high-glucose-induced oxidative stress, cell growth inhibition, and apoptosis, and downregulates YAP and GPX4 expression in human retinal capillary endothelial cells[1].
DL-pipecolic acid (1, 10, 100 μM; 20 min) potentiates population spike amplitude in the dentate gyrus of rat hippocampal slices at 10 and 100 μM, while D- and L-pipecolic acid show no significant inhibitory effect[2].
DL-pipecolic acid (10, 100 μM) does not significantly affect voltage-sensitive Na+ channel and voltage-sensitive K+ channel currents in Neuro-2A cells at 10 or 100 μM[2]. DL-pipecolic acid
DL-pipecolic acid (10, 100 μM) potentiates voltage-sensitive Ca2+ channel currents in cultured rat cortical neurons at 10 and 100 μM[2].
DL-pipecolic acid (1, 10, 100 μM; 72 h) reduces viability of Neuro-2A cells in a dose-dependent manner, with the most potent effect among D-, L-, and DL-enantiomers[2].
DL-pipecolic acid (100 μM; 72 h) induces cell death and apoptosis in Neuro-2A cells, as indicated by propidium iodide and Hoechst 33342 staining[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Pipecolic acid Related Antibodies

Cell Viability Assay[2]

Cell Line: Neuro-2A cells (mouse neuroblastoma cell line)
Concentration: 1, 10, 100 μM
Incubation Time: 72 h
Result: Reduced cell viability in a dose-dependent manner to 68 ± 4% (1 μM), 60 ± 6% (10 μM), and 48 ± 4% of control levels (100 μM); exhibited the most potent effect among D-, L-, and DL-enantiomers.
In Vivo

Pipecolic acid (250 mg/kg; i.g.; daily; 7 days) mitigates streptozotocin-induced diabetic retinopathy in male C57BL/6 mice by reducing oxidative stress, normalizing retinal iron content, and modulating YAP signaling, as evidenced by improved body weight gain, reduced retinal pathological changes, and corrected oxidative stress marker levels[1].
Pipecolic acid (250 mg/kg; i.g.; daily; 14 days) improves body weight gain and reduces retinal pathological changes in YAP knockout mice with streptozotocin-induced diabetic retinopathy, though its efficacy is diminished relative to its effects in wild-type mice[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: C57BL/6 (male, 8 weeks old, ~25 g, streptozotocin-induced type 1 diabetes)[1]
Dosage: 250 mg/kg
Administration: i.g.; daily; 7 days
Result: Achieved significantly higher body weight gain (11.04 ± 1.85 g) compared to untreated diabetic mice; reduced serum glucose levels; significantly decreased the ratio of retinal positive areas to whole positive areas; reversed diabetic-induced oxidative stress changes by reducing retinal malondialdehyde, reactive oxygen species, and iron content, while increasing retinal glutathione peroxidase, catalase, and superoxide dismutase levels; significantly increased retinal YAP mRNA expression compared to untreated diabetic mice; reduced the ratio of endothelial cells to pericytes, the number of acellular capillaries, and the level of mitophagy autosomes/nucleus in retinal tissue compared to untreated diabetic mice.
Animal Model: YAP knockout (male, streptozotocin-induced type 1 diabetes)[1]
Dosage: 250 mg/kg
Administration: i.g.; daily; 14 days
Result: Achieved significantly higher body weight gain compared to untreated YAP knockout diabetic mice; did not significantly affect blood glucose levels; reduced the ratio of retinal positive areas to whole positive areas, the ratio of endothelial cells to pericytes, the number of acellular capillaries, and the ratio of epithelial cells to retinal pericytes compared to untreated YAP knockout diabetic mice; significantly reduced retinal GPX4 and VEGF protein expression compared to untreated YAP knockout diabetic mice.
Molecular Weight

129.16

Formula

C6H11NO2
CAS No.
Appearance

Solid

Color

White to off-white

SMILES

O=C(O)C1CCCCN1
Shipping

Room temperature in continental US; may vary elsewhere.
Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

H2O : 50 mg/mL (387.12 mM; Need ultrasonic)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 7.7423 mL 38.7117 mL 77.4233 mL
5 mM 1.5485 mL 7.7423 mL 15.4847 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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This equation is commonly abbreviated as: C1V1 = C2V2

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In Vivo Dissolution Calculator
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Calculation results:
Working solution concentration: mg/mL
This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact MedChemExpress (MCE).
Purity & Documentation

Purity: 99.92%

SDS (393 KB)

COA (247 KB) HNMR (231 KB) RP-HPLC (245 KB)

Handling Instructions (2659 KB)
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
H2O 1 mM 7.7423 mL 38.7117 mL 77.4233 mL 193.5584 mL
5 mM 1.5485 mL 7.7423 mL 15.4847 mL 38.7117 mL
10 mM 0.7742 mL 3.8712 mL 7.7423 mL 19.3558 mL
15 mM 0.5162 mL 2.5808 mL 5.1616 mL 12.9039 mL
20 mM 0.3871 mL 1.9356 mL 3.8712 mL 9.6779 mL
25 mM 0.3097 mL 1.5485 mL 3.0969 mL 7.7423 mL
30 mM 0.2581 mL 1.2904 mL 2.5808 mL 6.4519 mL
40 mM 0.1936 mL 0.9678 mL 1.9356 mL 4.8390 mL
50 mM 0.1548 mL 0.7742 mL 1.5485 mL 3.8712 mL
60 mM 0.1290 mL 0.6452 mL 1.2904 mL 3.2260 mL
80 mM 0.0968 mL 0.4839 mL 0.9678 mL 2.4195 mL
100 mM 0.0774 mL 0.3871 mL 0.7742 mL 1.9356 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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Pipecolic acid Related Classifications

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  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Pipecolic acid535-75-1Endogenous MetaboliteYAPGlutathione PeroxidaseFerroptosisYes-associated proteinZellweger syndromeferroptosishuman retinal capillary endothelial cellsrat cortical neuronsglutathione peroxidase 4diabetic retinopathyYAP-GPX4 signaling pathwayNeuro-2A cellchronic liver diseasesInhibitorinhibitorinhibit

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