Lupeol

Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent androgen receptor (AR) inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC).

Product information

CAS Number: 545-47-1

Molecular Weight: 426.72

Formula: C30H50O

Synonym:

Clerodol

Monogynol B

Fagarasterol

Chemical Name: (1R, 3aR, 5aR, 5bR, 7aR, 9S, 11aR, 11bR, 13aR, 13bR)-3a, 5a, 5b, 8, 8, 11a-hexamethyl-1-(prop-1-en-2-yl)-icosahydro-1H-cyclopenta[a]chrysen-9-ol

Smiles: CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@H]2[C@H]3[C@@H](CC[C@]3(C)CC[C@@]12C)C(C)=C

InChiKey: MQYXUWHLBZFQQO-QGTGJCAVSA-N

InChi: InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 2 mg/mL (4.69 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Lupeol, an effective AR inhibitor, can be developed as a potential agent to treat human prostate cancer (CaP). Lupeol (10–50 μM) treatment for 48 h results in a dose-dependent growth inhibition of androgen-dependent phenotype (ADPC) cells viz., LAPC4 and LNCaP cells with an IC50 of 15.9 and 17.3 μM, respectively. Lupeol also inhibits the growth of 22Rν_1 with an IC50 of 19.1 μM. Further, Lupeol inhibits the growth of C4-2b cells with an IC50 of 25 μM. Lupeol has the potential to inhibit the growth of CaP cells of both ADPC and CRPC phenotype. Androgens by activating AR are known to drive the growth of CaP cells.

In Vivo:

Lupeol is an effective agent that has the potential to inhibit the tumorigenicity of CaP cells in vivo. At the conclusion of the study on day 56, the total circulating serum-PSA levels (secreted by the implanted tumor cells) are measured. At 56thday post-implantation, PSA levels are observed between 11.95-12.79 ng/mL in control animals with LNCaP-tumors and C4-2b-tumors, respectively. However, Lupeol-treated counterpart animals exhibits reduced serum-PSA levels in a range of 4.25-7.09 ng/mL. Tumor tissues of animals receiving Lupeol treatment exhibits reduced serum-PSA levels as compared to control.

References:

1. Siddique HR, et al. Lupeol, a novel androgen receptor inhibitor: implications in prostate cancer therapy. Clin Cancer Res. 2011 Aug 15;17(16):5379-91.

Products are for research use only. Not for human use.