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MedKoo Cat#: 581096 | Name: Pristimerin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pristimerin is an triterpenoid and an antitumor agent. Induces caspase-dependent apoptosis by inhibiting the chymotrypsin-like activity of the proteasome.

Chemical Structure

Pristimerin
CAS#1258-84-0

Theoretical Analysis

MedKoo Cat#: 581096

Name: Pristimerin

CAS#: 1258-84-0

Chemical Formula: C30H40O4

Exact Mass: 464.2927

Molecular Weight: 464.65

Elemental Analysis: C, 77.55; H, 8.68; O, 13.77

Price and Availability

Size Price Availability Quantity
10mg USD 400.00
25mg USD 700.00
50mg USD 1,200.00
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Related CAS #
No Data
Synonym
Pristimerin; Celastrol-methylether; UNII-28ZK7PR57S;
IUPAC/Chemical Name
methyl (2S,4aS,6aR,12bR,14aR,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate
InChi Key
JFACETXYABVHFD-KNSKBHFISA-N
InChi Code
InChI=1S/C30H40O4/c1-18-19-8-9-22-28(4,20(19)16-21(31)24(18)32)13-15-30(6)23-17-27(3,25(33)34-7)11-10-26(23,2)12-14-29(22,30)5/h8-9,16,23,32H,10-15,17H2,1-7H3/t23-,26-,27+,28+,29+,30-/m1/s1
SMILES Code
C[C@@]12CC[C@](C([C@](C)3CC4)=CC=C(C(C)=C5O)C3=CC5=O)(C)[C@@]4(C)[C@@H]1C[C@](C(OC)=O)(C)CC2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pristimerin is a potent and reversible monoacylglycerol lipase (MGL) inhibitor with an IC50 of 93 nM.
In vitro activity:
Treatment of pristimerin induced an increase in intracellular ROS, JNK activation, conformational change, and mitochondrial redistribution of Bax, mitochondrial membrane potential loss, and cell death. The PARP-1 was also found to be activated by pristimerin treatment. An antioxidant, N-acetyl-l-cysteine (NAC), inhibited pristimerin-induced JNK activation, Bax relocalization, and PARP-1 activation, as well as mitochondrial cell death. Reference: Mol Pharmacol. 2009 Oct;76(4):734-44. https://pubmed.ncbi.nlm.nih.gov/19574249/
In vivo activity:
The present study focused on the inhibition of angiogenesis by Pristimerin in adjuvant-induced arthritic rats and the underlying molecular mechanisms. Results clearly demonstrate for the first time that Pristimerin significantly reduces vessel density in synovial membrane tissues of inflamed joints and reduces the expression of pro-angiogenic factors in sera, including TNF-α, Ang-1, and MMP-9. Pristimerin also decreased the expression of VEGF and p-VEGFR2 in the synovial membrane, whereas the total amount of VEGFR2 remained unchanged. Reference: Int Immunopharmacol. 2015 Dec;29(2):302-313. https://pubmed.ncbi.nlm.nih.gov/26548348/
Solvent mg/mL mM comments
Solubility
DMF 22.5 48.42
DMSO 17.3 37.30
Ethanol 3.0 6.46
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 464.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Almaghrbi H, Elkardawy R, Udhaya Kumar S, Kuttikrishnan S, Abunada T, Kashyap MK, Ahmad A, Uddin S, George Priya Doss C, Zayed H. Analysis of signaling cascades from myeloma cells treated with pristimerin. Adv Protein Chem Struct Biol. 2023;134:147-174. doi: 10.1016/bs.apcsb.2022.10.006. Epub 2022 Nov 16. PMID: 36858733. 2. Byun JY, Kim MJ, Eum DY, Yoon CH, Seo WD, Park KH, Hyun JW, Lee YS, Lee JS, Yoon MY, Lee SJ. Reactive oxygen species-dependent activation of Bax and poly(ADP-ribose) polymerase-1 is required for mitochondrial cell death induced by triterpenoid pristimerin in human cervical cancer cells. Mol Pharmacol. 2009 Oct;76(4):734-44. doi: 10.1124/mol.109.056259. Epub 2009 Jul 2. PMID: 19574249. 3. Deng Q, Bai S, Gao W, Tong L. Pristimerin inhibits angiogenesis in adjuvant-induced arthritic rats by suppressing VEGFR2 signaling pathways. Int Immunopharmacol. 2015 Dec;29(2):302-313. doi: 10.1016/j.intimp.2015.11.001. Epub 2015 Nov 6. PMID: 26548348. 4. Tiedemann RE, Schmidt J, Keats JJ, Shi CX, Zhu YX, Palmer SE, Mao X, Schimmer AD, Stewart AK. Identification of a potent natural triterpenoid inhibitor of proteosome chymotrypsin-like activity and NF-kappaB with antimyeloma activity in vitro and in vivo. Blood. 2009 Apr 23;113(17):4027-37. doi: 10.1182/blood-2008-09-179796. Epub 2008 Dec 18. PMID: 19096011; PMCID: PMC3952546.
In vitro protocol:
1. Almaghrbi H, Elkardawy R, Udhaya Kumar S, Kuttikrishnan S, Abunada T, Kashyap MK, Ahmad A, Uddin S, George Priya Doss C, Zayed H. Analysis of signaling cascades from myeloma cells treated with pristimerin. Adv Protein Chem Struct Biol. 2023;134:147-174. doi: 10.1016/bs.apcsb.2022.10.006. Epub 2022 Nov 16. PMID: 36858733. 2. Byun JY, Kim MJ, Eum DY, Yoon CH, Seo WD, Park KH, Hyun JW, Lee YS, Lee JS, Yoon MY, Lee SJ. Reactive oxygen species-dependent activation of Bax and poly(ADP-ribose) polymerase-1 is required for mitochondrial cell death induced by triterpenoid pristimerin in human cervical cancer cells. Mol Pharmacol. 2009 Oct;76(4):734-44. doi: 10.1124/mol.109.056259. Epub 2009 Jul 2. PMID: 19574249.
In vivo protocol:
1. Deng Q, Bai S, Gao W, Tong L. Pristimerin inhibits angiogenesis in adjuvant-induced arthritic rats by suppressing VEGFR2 signaling pathways. Int Immunopharmacol. 2015 Dec;29(2):302-313. doi: 10.1016/j.intimp.2015.11.001. Epub 2015 Nov 6. PMID: 26548348. 2. Tiedemann RE, Schmidt J, Keats JJ, Shi CX, Zhu YX, Palmer SE, Mao X, Schimmer AD, Stewart AK. Identification of a potent natural triterpenoid inhibitor of proteosome chymotrypsin-like activity and NF-kappaB with antimyeloma activity in vitro and in vivo. Blood. 2009 Apr 23;113(17):4027-37. doi: 10.1182/blood-2008-09-179796. Epub 2008 Dec 18. PMID: 19096011; PMCID: PMC3952546.
1: Fu X, Jiao Y, Feng Y, Lin F, Zhang B, Mao Q, Wang J, Jiang W, Mou Y, Wang H, Wang S. Scaffold Hopping of Pristimerin Provides Derivatives Containing a Privileged Quinoxaline Substructure as Potent Autophagy Inducers in Breast Cancer Cells. J Nat Prod. 2024 Aug 23;87(8):1952-1964. doi: 10.1021/acs.jnatprod.4c00373. Epub 2024 Aug 6. PMID: 39106494. 2: Adomako AK, Gasu EN, Mensah JO, Borquaye LS. Antileishmanial natural products as potential inhibitors of the Leishmania pteridine reductase: insights from molecular docking and molecular dynamics simulations. In Silico Pharmacol. 2024 Jul 30;12(2):70. doi: 10.1007/s40203-024-00247-8. PMID: 39091898; PMCID: PMC11289227. 3: Nakano K, Yokota Y, Vu QV, Lagravinese F, Kataoka T. Structure-Activity Relationship of Oleanane-Type Pentacyclic Triterpenoids on Nuclear Factor κB Activation and Intracellular Trafficking and N-Linked Glycosylation of Intercellular Adhesion Molecule-1. Int J Mol Sci. 2024 May 30;25(11):6026. doi: 10.3390/ijms25116026. PMID: 38892215; PMCID: PMC11173061. 4: Wang Y, Chen T, Cong X, Li Y, Chen R, Zhang P, Sun X, Zhao S. [Pristimerin enhances cisplatin-induced apoptosis in nasopharyngeal carcinoma cells via ROS-mediated deactivation of the PI3K/AKT signaling pathway]. Nan Fang Yi Ke Da Xue Xue Bao. 2024 May 20;44(5):904-912. Chinese. doi: 10.12122/j.issn.1673-4254.2024.05.12. PMID: 38862448; PMCID: PMC11166717. 5: Hu WB, Liu YT, Li J, Wang Y, Sun XZ, Hua MY, Liu XT, Hui BN. Pristimerin exhibits anti-cancer activity by inducing ER stress and AKT/GSK3β pathway through increasing intracellular ROS production in human esophageal cancer cells. Toxicol In Vitro. 2024 Aug;99:105867. doi: 10.1016/j.tiv.2024.105867. Epub 2024 Jun 6. PMID: 38848824. 6: Prabhu KS, Jessy S, Kuttikrishnan S, Mujeeb F, Mariyam Z, Habeeba U, Ahmad N, Bhat AA, Uddin S. Anticancer Potential and Molecular Targets of Pristimerin in Human Malignancies. Pharmaceuticals (Basel). 2024 Apr 30;17(5):578. doi: 10.3390/ph17050578. PMID: 38794148; PMCID: PMC11123949. 7: Sun J, Tian Z, Wu J, Li J, Wang Q, Huang S, Wang M. Pristimerin Exerts Pharmacological Effects Through Multiple Signaling Pathways: A Comprehensive Review. Drug Des Devel Ther. 2024 May 18;18:1673-1694. doi: 10.2147/DDDT.S460093. PMID: 38779590; PMCID: PMC11110813. 8: Statement of Retraction: Pristimerin inhibits neuronal inflammation and protects cognitive function in mice with sepsis-induced brain injuries by regulating PI3K/Akt signalling. Pharm Biol. 2024 Dec;62(1):269. doi: 10.1080/13880209.2024.2323353. Epub 2024 Mar 5. PMID: 38441034. 9: Tao L, Xia X, Kong S, Wang T, Fan F, Wang W. Natural pentacyclic triterpenoid from Pristimerin sensitizes p53-deficient tumor to PARP inhibitor by ubiquitination of Chk1. Pharmacol Res. 2024 Mar;201:107091. doi: 10.1016/j.phrs.2024.107091. Epub 2024 Feb 4. PMID: 38316371. 10: Kundu S, Sarkar S, Acharya Chowdhury A. Anti-Leukemic Attributes of Natural Compounds Targeting Autophagy: A Closer Look into the Molecular Mechanisms. Nutr Cancer. 2024;76(3):236-251. doi: 10.1080/01635581.2024.2306682. Epub 2024 Feb 1. PMID: 38263604. 11: Mathur A, Singh A, Hussain Y, Mishra A, Meena A, Mishra N, Luqman S. Regulating pri/pre-microRNA up/down expressed in cancer proliferation, angiogenesis and metastasis using selected potent triterpenoids. Int J Biol Macromol. 2024 Feb;257(Pt 1):127945. doi: 10.1016/j.ijbiomac.2023.127945. Epub 2023 Nov 10. PMID: 37951434. 12: Jiang H, Xie Y, Lu J, Li H, Zeng K, Hu Z, Wu D, Yang J, Yao Z, Chen H, Gong X, Yu X. Pristimerin suppresses AIM2 inflammasome by modulating AIM2-PYCARD/ASC stability via selective autophagy to alleviate tendinopathy. Autophagy. 2024 Jan;20(1):76-93. doi: 10.1080/15548627.2023.2249392. Epub 2023 Aug 30. PMID: 37647255; PMCID: PMC10761048. 13: Fan Z, Jia W. Lactobacillus casei-derived postbiotics inhibited digestion of triglycerides, glycerol phospholipids and sterol lipids via allosteric regulation of BSSL, PTL and PLA2 to prevent obesity: perspectives on deep learning integrated multi-omics. Food Funct. 2023 Aug 14;14(16):7439-7456. doi: 10.1039/d3fo00809f. PMID: 37486034. 14: Caruso F, Rossi M, Eberhardt E, Berinato M, Sakib R, Surco-Laos F, Chavez H. Maytenus octogona Superoxide Scavenging and Anti-Inflammatory Caspase-1 Inhibition Study Using Cyclic Voltammetry and Computational Docking Techniques. Int J Mol Sci. 2023 Jun 28;24(13):10750. doi: 10.3390/ijms241310750. PMID: 37445927; PMCID: PMC10341947. 15: Lu Y, Zeng Z, Bao X, Wu M, Jing Z, Feng J. Pristimerin protects against pathological cardiac hypertrophy through improvement of PPARα pathway. Toxicol Appl Pharmacol. 2023 Aug 15;473:116572. doi: 10.1016/j.taap.2023.116572. Epub 2023 Jun 2. PMID: 37269933. 16: Wiart C, Kathirvalu G, Raju CS, Nissapatorn V, Rahmatullah M, Paul AK, Rajagopal M, Sathiya Seelan JS, Rusdi NA, Lanting S, Sulaiman M. Antibacterial and Antifungal Terpenes from the Medicinal Angiosperms of Asia and the Pacific: Haystacks and Gold Needles. Molecules. 2023 May 4;28(9):3873. doi: 10.3390/molecules28093873. PMID: 37175283; PMCID: PMC10180233. 17: Jia H, Liu T, Yang Q, Zheng H, Fu S, Hong J, Zhou Z, Huang Q, Zhang Z, Zhang H, Chen X, Sun R, Shan W. Tumor-Derived PD-L1+ Exosomes with Natural Inflammation Tropism for Psoriasis-Targeted Treatment. Bioconjug Chem. 2023 Apr 10. doi: 10.1021/acs.bioconjchem.3c00129. Epub ahead of print. PMID: 37036892. 18: Chen Y, Aili M, Chen F, Gong Y, Chen X, Zhang L. Drugs Targeting NLRP3 Inflammasome in the Treatment of Diabetic Bone Disorders. Endocr Metab Immune Disord Drug Targets. 2023;23(10):1265-1277. doi: 10.2174/1871530323666230320164235. PMID: 36959134. 19: Almaghrbi H, Elkardawy R, Udhaya Kumar S, Kuttikrishnan S, Abunada T, Kashyap MK, Ahmad A, Uddin S, George Priya Doss C, Zayed H. Analysis of signaling cascades from myeloma cells treated with pristimerin. Adv Protein Chem Struct Biol. 2023;134:147-174. doi: 10.1016/bs.apcsb.2022.10.006. Epub 2022 Nov 16. PMID: 36858733. 20: Chen C, Du S, Zhong W, Liu K, Qu L, Chu F, Yang J, Han X. Accurate delivery of pristimerin and paclitaxel by folic acid-linked nano-micelles for enhancing chemosensitivity in cancer therapy. Nano Converg. 2022 Nov 24;9(1):52. doi: 10.1186/s40580-022-00343-5. PMID: 36427092; PMCID: PMC9700544.

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