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MedKoo Cat#: 592973 | Name: Benproperine phosphate
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Description:

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

an inhibitor of cancer cell migration and an anti-metastatic agent. Benp selectively inhibited cancer cell migration and invasion, which also suppressed metastasis of cancer cells in animal models. Actin-related protein 2/3 complex subunit 2 (ARPC2) was identified as a molecular target of Benp by affinity column chromatography with Benp-tagged Sepharose beads. Benp bound directly to ARPC2 in cells, which was validated by pull-down assay using Benp-biotin and label-free biochemical methods such as the drug affinity responsive target stability (DARTS) and cellular thermal shift assay (CETSA). Benp inhibited Arp2/3 function, showing disruption of lamellipodial structure and inhibition of actin polymerization. Unlike Arp2/3 inhibitors, Benp selectively inhibited the migration of cancer cells but not normal cells.

Chemical Structure

Benproperine phosphate
Benproperine phosphate
CAS#3563-76-6

Theoretical Analysis

MedKoo Cat#: 592973

Name: Benproperine phosphate

CAS#: 3563-76-6

Chemical Formula: C21H30NO5P

Exact Mass: 407.1862

Molecular Weight: 407.45

Elemental Analysis: Chemical Formula: Exact Mass: Molecular Weight: Elemental Analysis: C, 61.91; H, 7.42; N, 3.44; O, 19.63; P, 7.60

Price and Availability

Size Price Availability Quantity
250mg USD 250.00 2 Weeks
500mg USD 400.00 2 Weeks
1g USD 650.00 2 Weeks
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Related CAS #
19428-14-9
Synonym
Benproperine phosphate; ASA 158-5; ASA158-5; ASA-158-5; BPP
IUPAC/Chemical Name
1-(1-(2-benzylphenoxy)propan-2-yl)piperidine phosphate
InChi Key
MCVUURBOSHQXMK-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H27NO.H3O4P/c1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19;1-5(2,3)4/h2,4-7,10-13,18H,3,8-9,14-17H2,1H3;(H3,1,2,3,4)
SMILES Code
O=P(O)(O)O.CC(COC1=CC=CC=C1CC2=CC=CC=C2)N3CCCCC3
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 407.45 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
1: Zhang H, Zhang Z, Huang Y, Qin S, Zhou L, Weng N, Liu J, Yang M, Zhang X, Lu Y, Ma L, Zheng S, Li Q. Repurposing antitussive benproperine phosphate against pancreatic cancer depends on autophagy arrest. Mol Oncol. 2021 Feb;15(2):725-738. doi: 10.1002/1878-0261.12854. Epub 2020 Dec 12. PMID: 33226737; PMCID: PMC7858282. 2: Jang HJ, Yoon YJ, Choi J, Lee YJ, Lee S, Cho W, Byun WG, Park SB, Han DC, Kwon BM. S-Benproperine, an Active Stereoisomer of Benproperine, Suppresses Cancer Migration and Tumor Metastasis by Targeting ARPC2. Pharmaceuticals (Basel). 2022 Nov 25;15(12):1462. doi: 10.3390/ph15121462. PMID: 36558913; PMCID: PMC9785746. 3: Yoon YJ, Han YM, Choi J, Lee YJ, Yun J, Lee SK, Lee CW, Kang JS, Chi SW, Moon JH, Lee S, Han DC, Kwon BM. Benproperine, an ARPC2 inhibitor, suppresses cancer cell migration and tumor metastasis. Biochem Pharmacol. 2019 May;163:46-59. doi: 10.1016/j.bcp.2019.01.017. Epub 2019 Jan 30. PMID: 30710516. 4: Wu D, Liu D, Zhang Y, Zhang Z, Li H. Unravelling the binding mechanism of benproperine with human serum albumin: A docking, fluorometric, and thermodynamic approach. Eur J Med Chem. 2018 Feb 25;146:245-250. doi: 10.1016/j.ejmech.2018.01.064. Epub 2018 Feb 4. PMID: 29407954. 5: Li Y, Zhong DF, Chen SW, Maeba I. Identification of some benproperine metabolites in humans and investigation of their antitussive effect. Acta Pharmacol Sin. 2005 Dec;26(12):1519-26. doi: 10.1111/j.1745-7254.2005.00212.x. PMID: 16297353. 6: Chen S, Min L, Li Y, Li W, Zhong D, Kong W. Anti-tussive activity of benproperine enantiomers on citric-acid-induced cough in conscious guinea-pigs. J Pharm Pharmacol. 2004 Feb;56(2):277-80. doi: 10.1211/0022357022719. PMID: 15005888. 7: Feng S, Liu J, Han X, Fan J. Resonance light scattering study on the interaction of benproperine phosphate with eriochrome blue black R in the presence of sodium dodecylbenzene sulphonate and its analytical application. Luminescence. 2009 Mar-Apr;24(2):67-72. doi: 10.1002/bio.1064. PMID: 18800357. 8: Li Y, Sun Y, Dong Y, Zhang Y, Zhong D. Identification and quantitative determination of benproperine metabolites in human plasma and urine by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jan 2;830(1):71-80. doi: 10.1016/j.jchromb.2005.10.011. Epub 2005 Nov 8. PMID: 16280263. 9: Du ZM, Huang HH, Chen XY, Zhong DF. [Study on hydroxylated metabolites of benproperine in human urine]. Yao Xue Xue Bao. 2000 Dec;35(12):916-20. Chinese. PMID: 12567915. 10: Du ZM, Zhong DF, Kang Y, Chen XY. [Enantioselective pharmacokinetics of benproperine in healthy volunteers]. Yao Xue Xue Bao. 2000 Dec;35(12):909-12. Chinese. PMID: 12567913. 11: Ida H. The nonnarcotic antitussive drug dimemorfan: a review. Clin Ther. 1997 Mar-Apr;19(2):215-31. doi: 10.1016/s0149-2918(97)80111-7. PMID: 9152562. 12: Yang XJ, Yang XY. [Determination of benproperine phosphate tablets by high performance liquid chromatography]. Se Pu. 2000 Nov;18(6):566-7. Chinese. PMID: 12541753. 13: O'Connor JJ. Argon laser treatment of radiation proctitis. Arch Surg. 1989 Jun;124(6):749. doi: 10.1001/archsurg.1989.01410060121027. PMID: 2730331. 14: Fang F, Qi Y, Lu F, Yang L. Highly sensitive on-site detection of drugs adulterated in botanical dietary supplements using thin layer chromatography combined with dynamic surface enhanced Raman spectroscopy. Talanta. 2016;146:351-7. doi: 10.1016/j.talanta.2015.08.067. Epub 2015 Sep 1. PMID: 26695274. 15: Liu MY, Meng Y, Ren YL, Zhang HQ. [Nondestructive quantitative analysis of Cofrel medicines by improved partial least squares-NIR spectroscopy]. Guang Pu Xue Yu Guang Pu Fen Xi. 2007 Jun;27(6):1098-101. Chinese. PMID: 17763766. 16: Huang NK, Lichtenstein AH, Matuszek G, Matthan NR. Comparison of Plasma Metabolome Response to Diets Enriched in Soybean and Partially-Hydrogenated Soybean Oil in Moderately Hypercholesterolemic Adults-A Pilot Study. Metabolites. 2023 Mar 26;13(4):474. doi: 10.3390/metabo13040474. PMID: 37110133; PMCID: PMC10140885. 17: Yanaura S, Kitagawa H, Hosokawa T, Misawa M. A new screening method for evaluating antitussives in conscious guinea pigs. J Pharmacobiodyn. 1982 Dec;5(12):965-71. doi: 10.1248/bpb1978.5.965. PMID: 7169609.

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