Leelamine free base | CAS#1446-61-3 | hepatic cytochrome P450 2B activity inducer

MedKoo Cat#: 561542 | Name: Leelamine free base

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Description:

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

Leelamine, also known as NSC-2955, is a selective and potent inducer of hepatic cytochrome P450 2B activity. It is also an inhibitor of intracellular cholesterol transport.

Chemical Structure

Leelamine free base

CAS#1446-61-3 (free base)

Theoretical Analysis

MedKoo Cat#: 561542

Name: Leelamine free base

CAS#: 1446-61-3 (free base)

Chemical Formula: C20H31N

Exact Mass: 285.2457

Molecular Weight: 285.48

Elemental Analysis: C, 84.15; H, 10.95; N, 4.91

Price and Availability

Size	Price	Availability	Quantity
25g	USD 350.00	2 Weeks

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Related CAS #

16496-99-4 (HCl) 1446-61-3 (free base)

Synonym

Dehydroabietylamine; Leelamine free base; Leelamine; NSC-2955; NSC 2955; NSC2955;

IUPAC/Chemical Name

((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methanamine

InChi Key

JVVXZOOGOGPDRZ-SLFFLAALSA-N

InChi Code

InChI=1S/C20H31N/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12,14,18H,5,7,9-11,13,21H2,1-4H3/t18-,19-,20+/m0/s1

SMILES Code

CC(C)C1=CC2=C([C@](CCC[C@]3(CN)C)(C)[C@H]3CC2)C=C1

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:

Leelamine is a weak agonist of cannabinoid receptors CB1 and CB2. Leelamine also inhibits pyruvate dehydrogenase kinases (PDKs).

In vitro activity:

LEE (leelamine) suppressed expression of CXCR7 and CXCR4 both at the protein and mRNA levels, and showed inhibitory effects on these chemokines even after stimulation by CXCL12 ligand. In addition, LEE also reduced the level of MnSOD and inhibited the EMT process to attenuate the invasion and migration of breast cancer cells. Reference: Int J Mol Sci. 2022 Aug 30;23(17):9848. https://pubmed.ncbi.nlm.nih.gov/36077241/

In vivo activity:

A trend for a decrease in expression level of cMyc protein was discernible in 22Rv1 xenografts from LLM (leelamine)-treated mice compared with control mice. The LLM treatment (10 mg/kg body weight, 5 times/week) was well-tolerated by Hi-Myc transgenic mice. Reference: J Cancer Metastasis Treat. 2021;7:16. https://pubmed.ncbi.nlm.nih.gov/34660908/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	105.09
	DMSO	65.0	227.69
	Ethanol	100.0	350.29
	Ethanol:PBS (pH 7.2) (1:3)	0.3	0.88

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 285.48 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. Jung YY, Um JY, Sethi G, Ahn KS. Potential Application of Leelamine as a Novel Regulator of Chemokine-Induced Epithelial-to-Mesenchymal Transition in Breast Cancer Cells. Int J Mol Sci. 2022 Aug 30;23(17):9848. doi: 10.3390/ijms23179848. PMID: 36077241; PMCID: PMC9456465. 2. Sin ZW, Mohan CD, Chinnathambi A, Govindasamy C, Rangappa S, Rangappa KS, Jung YY, Ahn KS. Leelamine Exerts Antineoplastic Effects in Association with Modulating Mitogen‑Activated Protein Kinase Signaling Cascade. Nutr Cancer. 2022;74(9):3375-3387. doi: 10.1080/01635581.2022.2059092. Epub 2022 May 17. PMID: 35579498. 3. Singh KB, Hahm ER, Singh SV. Leelamine suppresses cMyc expression in prostate cancer cells in vitro and inhibits prostate carcinogenesis in vivo. J Cancer Metastasis Treat. 2021;7:16. doi: 10.20517/2394-4722.2021.08. Epub 2021 Mar 26. PMID: 34660908; PMCID: PMC8513473. 4. Singh KB, Hahm ER, Pore SK, Singh SV. Leelamine Is a Novel Lipogenesis Inhibitor in Prostate Cancer Cells In Vitro and In Vivo. Mol Cancer Ther. 2019 Oct;18(10):1800-1810. doi: 10.1158/1535-7163.MCT-19-0046. Epub 2019 Aug 8. PMID: 31395683; PMCID: PMC6774899.

In vitro protocol:

In vivo protocol:

1. Singh KB, Hahm ER, Singh SV. Leelamine suppresses cMyc expression in prostate cancer cells in vitro and inhibits prostate carcinogenesis in vivo. J Cancer Metastasis Treat. 2021;7:16. doi: 10.20517/2394-4722.2021.08. Epub 2021 Mar 26. PMID: 34660908; PMCID: PMC8513473. 2. Singh KB, Hahm ER, Pore SK, Singh SV. Leelamine Is a Novel Lipogenesis Inhibitor in Prostate Cancer Cells In Vitro and In Vivo. Mol Cancer Ther. 2019 Oct;18(10):1800-1810. doi: 10.1158/1535-7163.MCT-19-0046. Epub 2019 Aug 8. PMID: 31395683; PMCID: PMC6774899.

1: Chen YC, Gowda R, Newswanger RK, Leibich P, Fell B, Rosenberg G, Robertson GP. Targeting cholesterol transport in circulating melanoma cells to inhibit metastasis. Pigment Cell Melanoma Res. 2017 Jan;30(6):541-552. doi: 10.1111/pcmr.12614. Epub 2017 Oct 15. PubMed PMID: 28685959. 2: Gowda R, Inamdar GS, Kuzu O, Dinavahi SS, Krzeminski J, Battu MB, Voleti SR, Amin S, Robertson GP. Identifying the structure-activity relationship of leelamine necessary for inhibiting intracellular cholesterol transport. Oncotarget. 2017 Apr 25;8(17):28260-28277. doi: 10.18632/oncotarget.16002. PubMed PMID: 28423677; PubMed Central PMCID: PMC5438648. 3: Kuzu OF, Toprak M, Noory MA, Robertson GP. Effect of lysosomotropic molecules on cellular homeostasis. Pharmacol Res. 2017 Mar;117:177-184. doi: 10.1016/j.phrs.2016.12.021. Epub 2016 Dec 23. Review. PubMed PMID: 28025106. 4: Sehrawat A, Kim SH, Hahm ER, Arlotti JA, Eiseman J, Shiva SS, Rigatti LH, Singh SV. Cancer-selective death of human breast cancer cells by leelamine is mediated by bax and bak activation. Mol Carcinog. 2017 Feb;56(2):337-348. doi: 10.1002/mc.22497. Epub 2016 May 5. PubMed PMID: 27149078; PubMed Central PMCID: PMC5097706. 5: Zhang Y, Tian D, Matsuyama H, Hamazaki T, Shiratsuchi T, Terada N, Hook DJ, Walters MA, Georg GI, Hawkinson JE. Human Adenine Nucleotide Translocase (ANT) Modulators Identified by High-Throughput Screening of Transgenic Yeast. J Biomol Screen. 2016 Apr;21(4):381-90. doi: 10.1177/1087057115624637. Epub 2016 Jan 8. PubMed PMID: 26746582. 6: Gowda R, Madhunapantula SV, Sharma A, Kuzu OF, Robertson GP. Nanolipolee-007, a novel nanoparticle-based drug containing leelamine for the treatment of melanoma. Mol Cancer Ther. 2014 Oct;13(10):2328-40. doi: 10.1158/1535-7163.MCT-14-0357. Epub 2014 Jul 31. PubMed PMID: 25082958; PubMed Central PMCID: PMC4377120. 7: Sim J, Nam W, Lee D, Lee S, O H, Joo J, Liu KH, Han JY, Ki SH, Jeong TC, Lee T, Lee S. Selective induction of hepatic cytochrome P450 2B activity by leelamine in vivo, as a potent novel inducer. Arch Pharm Res. 2015;38(5):725-33. doi: 10.1007/s12272-014-0443-0. Epub 2014 Jul 23. PubMed PMID: 25052955. 8: Kuzu OF, Gowda R, Sharma A, Robertson GP. Leelamine mediates cancer cell death through inhibition of intracellular cholesterol transport. Mol Cancer Ther. 2014 Jul;13(7):1690-703. doi: 10.1158/1535-7163.MCT-13-0868. Epub 2014 Mar 31. PubMed PMID: 24688051; PubMed Central PMCID: PMC4373557. 9: Gowda R, Madhunapantula SV, Kuzu OF, Sharma A, Robertson GP. Targeting multiple key signaling pathways in melanoma using leelamine. Mol Cancer Ther. 2014 Jul;13(7):1679-89. doi: 10.1158/1535-7163.MCT-13-0867. Epub 2014 Mar 31. PubMed PMID: 24688050; PubMed Central PMCID: PMC4377161. 10: Song M, Lee D, Lee T, Lee S. Determination of leelamine in mouse plasma by LC-MS/MS and its pharmacokinetics. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Jul 15;931:170-3. doi: 10.1016/j.jchromb.2013.05.018. Epub 2013 May 28. PubMed PMID: 23797112. 11: Cadoudal T, Distel E, Durant S, Fouque F, Blouin JM, Collinet M, Bortoli S, Forest C, Benelli C. Pyruvate dehydrogenase kinase 4: regulation by thiazolidinediones and implication in glyceroneogenesis in adipose tissue. Diabetes. 2008 Sep;57(9):2272-9. doi: 10.2337/db08-0477. Epub 2008 Jun 2. PubMed PMID: 18519799; PubMed Central PMCID: PMC2518477.