Synonym
Lithocolic acid; Lithocholate;
IUPAC/Chemical Name
3alpha-Hydroxy-5beta-cholan-24-oic acid
InChi Key
SMEROWZSTRWXGI-HVATVPOCSA-N
InChi Code
InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1
SMILES Code
C[C@H](CCC(O)=O)[C@H]1CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
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
Biological target:
Lithocholic acid is a toxic secondary bile acid, causes intrahepatic cholestasis, has tumor-promoting activity.
In vitro activity:
Using this assay, this study found that LCA (lithocholic acid) exhibits a potent and selective anti-tumor effect in several lines of cultured human NB cells. In fact, this bile acid killed the NB cell lines BE(2)-m17, SK-n-SH, SK-n-MCIXC and Lan-1 if used at concentrations that were not cytotoxic or only mildly cytotoxic (as in case of Lan-1) to primary cultures of human neurons (Fig. (Fig.1A).
Reference: Oncotarget. 2011 Oct;2(10):761-82. https://pubmed.ncbi.nlm.nih.gov/21992775/
In vivo activity:
After LCA (lithocolic acid) exposure, the liver mass of Smad3-null mice was smaller than that of LCA-treated wild-type mice (Fig. 2A). In addition, LCA-increased serum ALP activities were significantly attenuated in the Smad3-null mice, although serum ALT activities were not changed (Fig. 2B, C). These results suggest that TGFβ-SMAD3 signaling is associated with the LCA-induced biliary injury and raise the possibility that TGFβ-SMAD3 signaling alters hepatic metabolism.
Reference: J Lipid Res. 2012 Dec;53(12):2698-707. https://pubmed.ncbi.nlm.nih.gov/23034213/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF:PBS (pH 7.2) (1:1) |
0.5 |
1.33 |
|
| DMSO |
20.0 |
53.11 |
|
| Ethanol |
20.0 |
53.11 |
|
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
376.58
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.
| 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. Goldberg AA, Beach A, Davies GF, Harkness TA, Leblanc A, Titorenko VI. Lithocholic bile acid selectively kills neuroblastoma cells, while sparing normal neuronal cells. Oncotarget. 2011 Oct;2(10):761-82. doi: 10.18632/oncotarget.338. PMID: 21992775; PMCID: PMC3248158.
2. Makishima M, Lu TT, Xie W, Whitfield GK, Domoto H, Evans RM, Haussler MR, Mangelsdorf DJ. Vitamin D receptor as an intestinal bile acid sensor. Science. 2002 May 17;296(5571):1313-6. doi: 10.1126/science.1070477. PMID: 12016314.
3. Matsubara T, Tanaka N, Sato M, Kang DW, Krausz KW, Flanders KC, Ikeda K, Luecke H, Wakefield LM, Gonzalez FJ. TGF-β-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury. J Lipid Res. 2012 Dec;53(12):2698-707. doi: 10.1194/jlr.M031773. Epub 2012 Oct 3. PMID: 23034213; PMCID: PMC3494264.
4. Kozoni V, Tsioulias G, Shiff S, Rigas B. The effect of lithocholic acid on proliferation and apoptosis during the early stages of colon carcinogenesis: differential effect on apoptosis in the presence of a colon carcinogen. Carcinogenesis. 2000 May;21(5):999-1005. doi: 10.1093/carcin/21.5.999. PMID: 10783324.
In vitro protocol:
1. Goldberg AA, Beach A, Davies GF, Harkness TA, Leblanc A, Titorenko VI. Lithocholic bile acid selectively kills neuroblastoma cells, while sparing normal neuronal cells. Oncotarget. 2011 Oct;2(10):761-82. doi: 10.18632/oncotarget.338. PMID: 21992775; PMCID: PMC3248158.
2. Makishima M, Lu TT, Xie W, Whitfield GK, Domoto H, Evans RM, Haussler MR, Mangelsdorf DJ. Vitamin D receptor as an intestinal bile acid sensor. Science. 2002 May 17;296(5571):1313-6. doi: 10.1126/science.1070477. PMID: 12016314.
In vivo protocol:
1. Matsubara T, Tanaka N, Sato M, Kang DW, Krausz KW, Flanders KC, Ikeda K, Luecke H, Wakefield LM, Gonzalez FJ. TGF-β-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury. J Lipid Res. 2012 Dec;53(12):2698-707. doi: 10.1194/jlr.M031773. Epub 2012 Oct 3. PMID: 23034213; PMCID: PMC3494264.
2. Kozoni V, Tsioulias G, Shiff S, Rigas B. The effect of lithocholic acid on proliferation and apoptosis during the early stages of colon carcinogenesis: differential effect on apoptosis in the presence of a colon carcinogen. Carcinogenesis. 2000 May;21(5):999-1005. doi: 10.1093/carcin/21.5.999. PMID: 10783324.
1: Shellman Z, Aldhahrani A, Verdon B, Mather M, Paleri V, Wilson J, Pearson J, Ward C, Powell J. Bile acids: a potential role in the pathogenesis of pharyngeal malignancy. Clin Otolaryngol. 2017 Oct;42(5):969-973. doi: 10.1111/coa.12822. Epub 2017 Jan 18. PubMed PMID: 28036160.
2: Epstein D, Mistry K, Whitelaw A, Watermeyer G, Pettengell KE. The effect of physiological concentrations of bile acids on in vitro growth of Mycobacterium tuberculosis. S Afr Med J. 2012 May 23;102(6):522-4. PubMed PMID: 22668954.
3: Maeshima H, Ohno K, Tanaka-Azuma Y, Nakano S, Yamada T. Identification of tumor promotion marker genes for predicting tumor promoting potential of chemicals in BALB/c 3T3 cells. Toxicol In Vitro. 2009 Feb;23(1):148-57. doi: 10.1016/j.tiv.2008.10.005. Epub 2008 Nov 1. PubMed PMID: 19000923.
4: Di Mauro S, Cesario E, Bartolo V, Maglitto D, Nucita R, Di Mauro L. [Nutritional habits and colon-rectal tumours]. Minerva Gastroenterol Dietol. 2004 Jun;50(2):135-41. Review. Italian. PubMed PMID: 15722983.
5: Thomas MG, Owen RW, Alexander B, Williamson RC. Effect of enteral feeding on intestinal epithelial proliferation and fecal bile acid profiles in the rat. JPEN J Parenter Enteral Nutr. 1993 May-Jun;17(3):210-3. PubMed PMID: 7685051.
6: Fujiwara S, Ku Y, Saitoh Y. Serum bile acid monitoring as an early indicator of allograft function in canine orthotopic liver transplantation. Kobe J Med Sci. 1992 Aug;38(4):217-31. PubMed PMID: 1469887.
7: MCLAREN DS. LITHOCOLIC ACID AND BILIARY DUCTULAR CELLULAR REACTION IN ANIMALS. Nutr Rev. 1964 Oct;22:305-7. PubMed PMID: 14221336.
