2ccPA
2ccPA (2ccPA18:1) is a metabolically stabilized carba analog of cyclic phosphatidic acid (cPA). 2ccPA inhibits autotaxin (ATX)‑mediated lysophosphatidic acid (LPA) production, suppresses extracellular matrix biosynthesis and elevates intracellular cAMP in fibrogenic skin fibroblasts. 2ccPA protects oligodendrocytes from mitochondrial‑driven apoptosis, suppresses neuroinflammation and demyelination, modulates microglial polarization and promotes rapid‑platelet/fibrin‑dependent hemostasis and subsequent fibrinolytic transition following brain injury.
For research use only. We do not sell to patients.
- CAS No.: 633278-53-2
- Formula: C22H41O5P
- Molecular Weight:416.53
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
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Collagen I |
2ccPA (2ccPA18:1) (1-10 μM; 48-72 h) does not reduce the viability of SSc skin fibroblasts or healthy skin fibroblasts, while 2ccPA (100 μM; 48-72 h) significantly reduces viability of SSc skin fibroblasts at these time points[1].
2ccPA (10 μM; 48 h) inhibits the upregulation of profibrotic mRNA markers (COL1A1, COL1A2, CTGF, ACTA2) in TGF-β1-stimulated healthy skin fibroblasts[1].
2ccPA (10 μM; 72 h) reduces the protein expression of profibrotic markers (type I collagen, CCN2, αSMA) in TGF-β1-stimulated healthy skin fibroblasts[1].
2ccPA (1-10 μM; 48 h) dose-dependently reduces profibrotic mRNA marker (COL1A1, COL1A2, CTGF, ACTA2) expression in SSc skin fibroblasts, and 2ccPA (10 μM; 6-48 h) maintains this inhibitory effect on additional markers (FN, TGF-β1) for up to 48 h[1].
2ccPA (10 μM; 48 h) reduces the protein expression of type I collagen and CCN2 in SSc skin fibroblasts, but 2ccPA (10 μM; 72 h) does not significantly decrease procollagen type I levels in culture supernatant[1].
2ccPA (10 μM; 24 h) significantly elevates the production of antifibrotic factors HGF and PGE2 in SSc skin fibroblasts[1].
2ccPA (1-10 μM; 30 min) dose-dependently increases intracellular cAMP levels in SSc skin fibroblasts[1].
2ccPA (10 μM; 2 days) increases cell viability, decreases the Bax/Bcl-2 ratio, and suppresses p38MAPK and JNK phosphorylation in MO3.13 oligodendrocyte-like cells, thereby attenuating mitochondrial apoptosis[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:systemic sclerosis (SSc) skin fibroblasts, healthy skin fibroblasts
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Concentration:1, 10, 100 μM
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Incubation Time:48 h, 72 h
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Result:Did not affect the viability of SSc skin fibroblasts and healthy skin fibroblasts at 1-10 μM for 48 or 72 h.
Significantly reduced SSc skin fibroblast viability at 100 μM for 48 and 72 h.
Showed a similar viability profile in healthy skin fibroblasts.
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Cell Line:healthy skin fibroblasts treated with TGF-β1
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Concentration:10 μM
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Incubation Time:48 h
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Result:Downregulated the mRNA expression levels of extracellular matrix (ECM) molecules COL1A1, COL1A2, CTGF, and ACTA2 in TGF-β1-stimulated healthy skin fibroblasts.
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Cell Line:healthy skin fibroblasts treated with TGF-β1
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Concentration:10 μM
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Incubation Time:72 h
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Result:Decreased the protein expression levels of type I collagen, CCN2, and αSMA in TGF-β1-stimulated healthy skin fibroblasts.
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Cell Line:systemic sclerosis (SSc) skin fibroblasts
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Concentration:1, 10 μM
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Incubation Time:6 h, 24 h, 48 h
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Result:Downregulated the mRNA expression levels of COL1A1, COL1A2, CTGF, and ACTA2 in SSc skin fibroblasts in a dose-dependent manner after 48 h.
Significantly reduced mRNA expression of COL1A1, COL1A2, CTGF, ACTA2, FN, and TGF-β1 compared to untreated cells after 6, 24, or 48 h, with the antifibrotic effect detectable up to 48 h.
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Cell Line:systemic sclerosis (SSc) skin fibroblasts
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Concentration:10 μM
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Incubation Time:24 h
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Result:Significantly increased the levels of HGF and PGE2 in the culture medium of SSc skin fibroblasts compared to untreated cells.
2ccPA (1.6 mg/kg; i.p.; once daily; 0-5 weeks) nearly completely suppresses acute peak demyelination, increases the number of myelinated axons, and suppresses Iba1, GFAP, NLRP3, P2X7R, IL-1β upregulation and microglial activation in C57BL/6J mice[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:BALB/c (6-week-old female; bleomycin-induced skin fibrosis)[1]
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Dosage:1, 10 mg/kg
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Administration:i.p.; once daily for 4 weeks
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Result:Reduced skin thickness and collagen content by 22.5% (not significant) at 1 mg/kg/day compared with Bleomycin-only controls.
Reduced skin thickness, reduced collagen content by 32%, and reduced αSMA-positive myofibroblast count by 45% at 10 mg/kg/day compared with Bleomycin-only controls.
Showed no side effects or significant body weight reduction.
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Animal Model:Male C57BL/6J mice[2]
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Dosage:1.6 mg/kg
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Administration:i.p.; once daily for 5 weeks
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Result:Nearly completely suppressed acute peak demyelination and reduced neuroinflammation.
Chemical Information
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CAS No. 633278-53-2
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Molecular Weight 416.53
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Formula C22H41O5P
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SMILES
CCCCCCCC/C=C\CCCCCCCC(OCC1COP(O)(C1)=O)=O
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Synonyms
2ccPA18:1
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Higuchi T, et al. Antifibrotic effects of 2-carba cyclic phosphatidic acid (2ccPA) in systemic sclerosis: contribution to the novel treatment. Arthritis Res Ther. 2019 Apr 18;21(1):103. [Content Brief]
[2]. Yamamoto S, et al. Correction to: Protective and therapeutic role of 2-carbacyclic phosphatidic acid in demyelinating disease. J Neuroinflammation. 2018 Mar 5;15(1):67. [Content Brief]
[3]. Hashimoto K, et al. 2-carba cyclic phosphatidic acid suppresses inflammation via regulation of microglial polarisation in the stab-wounded mouse cerebral cortex. Sci Rep. 2018 Jun 26;8(1):9715. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
2ccPA Related Classifications
HY-167201 Related Classifications
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