Prangol
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MedKoo CAT#: 464674

CAS#: 2643-85-8

Description: Prangol is a furanocoumarin that has been found in A. japonica and has diverse biological activities. It is active against the Gram-positive bacteria B. cereus, S. aureus, and S. faecalis (MICs = 9.76-78.12 µg/ml), the Gram-negative bacteria E. coli, S. dysenteriae, P. aeruginosa, K. pneumoniae, and S. typhi (MICs = 39.06-625 µg/ml), and the fungi C. albicans and M. audouinii (MIC = 39.06 µg/ml for both). Prangol inhibits proliferation of human MK-1 gastric and HeLa cervical cancer cells, as well as murine B16/F10 melanoma cells (EC50s = 47.2, 80.3, and 42 µg/ml, respectively). It also inhibits proliferation of sensitive and multidrug-resistant murine L5178Y lymphoma cells (IC50s = 41.96 and 60.58 µM, respectively).

Chemical Structure

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Prangol
CAS# 2643-85-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464674
Name: Prangol
CAS#: 2643-85-8
Chemical Formula: C16H16O6
Exact Mass: 304.09
Molecular Weight: 304.298
Elemental Analysis: C, 63.15; H, 5.30; O, 31.55

Price and Availability

Size Price Availability Quantity
100mg USD -2 2 Weeks
200mg USD -2 2 Weeks
500mg USD -2 2 Weeks
1g USD -2 2 Weeks
2g USD -2 2 Weeks
5mg USD 260 2 Weeks
10mg USD 430 2 Weeks
25mg USD 750 2 Weeks
50mg USD 1120 2 Weeks
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Synonym: Prangol; Prangolarin hydrate; (+)-Aviprin; (+) Aviprin; (+)-Oxypeucedanin hydrate; (+) Oxypeucedanin hydrate;

IUPAC/Chemical Name: (R)-4-(2,3-dihydroxy-3-methylbutoxy)-7H-furo[3,2-g]chromen-7-one

InChi Key: PEWFWDOPJISUOK-CYBMUJFWSA-N

InChi Code: InChI=1S/C16H16O6/c1-16(2,19)13(17)8-21-15-9-3-4-14(18)22-12(9)7-11-10(15)5-6-20-11/h3-7,13,17,19H,8H2,1-2H3/t13-/m1/s1

SMILES Code: CC(O)([C@@H](COC1=C2C=COC2=CC(O3)=C1C=CC3=O)O)C

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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: Oxypeucedanin hydrate ((+)-Oxypeucedanin hydrate) is a natural product isolated from D. anethifolia. Prangol exhibits mild toxicity on fibroblasts and parental lymphoma cells.
In vitro activity: Microsomal incubation with oxypeucedanin induced a time-, concentration-, and NADPH-dependent inhibition of CYPs2B6 and 2D6 with kinetic values of KI/kinact 1.82 μM/0.07 min-1 (CYP2B6) and 8.47 μM/0.044 min-1 (CYP2D6), respectively. Ticlopidine and quinidine attenuated the observed time-dependent enzyme inhibitions. An epoxide and/or γ-ketoenal intermediate(s) derived from oxypeucedanin was/were trapped in microsomal incubations. CYP3A4 was the primary enzyme involved in the bioactivation of oxypeucedanin. Reference: Curr Drug Metab. 2021;22(11):882-892. https://pubmed.ncbi.nlm.nih.gov/34191696/
In vivo activity: Using myeloperoxidase activity measurement, ELISA, qRT-PCR, and Western blotting, this study found that oxypeucedanin modulated the activity of myeloperoxidase and decreased the expression levels of inflammatory mediators such as TNF-α, IL-6, IL-1β, MPO, COX-2 and iNOS in LPS-induced inflammation models. Meanwhile, oxypeucedanin inhibited the activation of PI3K/AKT and its downstream NF-κB and MAPK signaling pathways. In addition, oxypeucedanin significantly decreased the pulmonary vascular permeability, which was induced by LPSs, and the enhanced expression of tight junction proteins (Occludin and Claudin 3). Reference: Aging (Albany NY). 2022 Aug 18;14(16):6626-6641. https://pubmed.ncbi.nlm.nih.gov/35985771/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 98.59
DMSO 30.0 98.59
DMSO:PBS (pH 7.2) (1:2) 0.3 1.08
Ethanol 5.0 16.43

Preparing Stock Solutions

The following data is based on the product molecular weight 304.30 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. Zhang K, Li Y, Fu Y, Cui T, Wang Q, Mao X, Peng Y, Zheng J. Oxypeucedanin is a Mechanism-based Inactivator of CYP2B6 and CYP2D6. Curr Drug Metab. 2021;22(11):882-892. doi: 10.2174/1389200222666210629114830. PMID: 34191696. 2. Park SH, Hong JY, Park HJ, Lee SK. The Antiproliferative Activity of Oxypeucedanin via Induction of G2/M Phase Cell Cycle Arrest and p53-Dependent MDM2/p21 Expression in Human Hepatoma Cells. Molecules. 2020 Jan 23;25(3):501. doi: 10.3390/molecules25030501. PMID: 31979361; PMCID: PMC7037124. 3. Du L, Zhang J, Zhang X, Li C, Wang Q, Meng G, Kan X, Zhang J, Jia Y. Oxypeucedanin relieves LPS-induced acute lung injury by inhibiting the inflammation and maintaining the integrity of the lung air-blood barrier. Aging (Albany NY). 2022 Aug 18;14(16):6626-6641. doi: 10.18632/aging.204235. Epub 2022 Aug 18. PMID: 35985771; PMCID: PMC9467393.
In vitro protocol: 1. Zhang K, Li Y, Fu Y, Cui T, Wang Q, Mao X, Peng Y, Zheng J. Oxypeucedanin is a Mechanism-based Inactivator of CYP2B6 and CYP2D6. Curr Drug Metab. 2021;22(11):882-892. doi: 10.2174/1389200222666210629114830. PMID: 34191696. 2. Park SH, Hong JY, Park HJ, Lee SK. The Antiproliferative Activity of Oxypeucedanin via Induction of G2/M Phase Cell Cycle Arrest and p53-Dependent MDM2/p21 Expression in Human Hepatoma Cells. Molecules. 2020 Jan 23;25(3):501. doi: 10.3390/molecules25030501. PMID: 31979361; PMCID: PMC7037124.
In vivo protocol: 1. Du L, Zhang J, Zhang X, Li C, Wang Q, Meng G, Kan X, Zhang J, Jia Y. Oxypeucedanin relieves LPS-induced acute lung injury by inhibiting the inflammation and maintaining the integrity of the lung air-blood barrier. Aging (Albany NY). 2022 Aug 18;14(16):6626-6641. doi: 10.18632/aging.204235. Epub 2022 Aug 18. PMID: 35985771; PMCID: PMC9467393.

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1: Ali I, Mu Y, Atif M, Hussain H, Li J, Li D, Shabbir M, Bankeu JJK, Cui L, Sajjad S, Wang D, Wang X. Separation and anti-inflammatory evaluation of phytochemical constituents from Pleurospermum candollei (Apiaceae) by high-speed counter-current chromatography with continuous sample load. J Sep Sci. 2021 Apr 29. doi: 10.1002/jssc.202100155. Epub ahead of print. PMID: 33914393.

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