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16496-99-4

16496-99-4 Structure

16496-99-4 Structure
IdentificationBack Directory
[Name]

(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1-,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanamine hydrochloride
[CAS]

16496-99-4
[Synonyms]

Dehydroabietylamine Hydrochloride
DehydroabiethylaMine Hydrochloride
(+)-DehydroabiethylaMine Hydrochloride
13-Isopropyl-podocarpa-8,11,13-trien-15-aMine Hydrochloride
((1S,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methanamine hydrochloride
(1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1-,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenemethanamine hydrochloride
[Molecular Formula]

C20H32ClN
[MOL File]

16496-99-4.mol
[Molecular Weight]

321.928
Chemical PropertiesBack Directory
[storage temp. ]

-20°
[solubility ]

Soluble in DMSO (up to 40 mg/ml) or in Water (up to 9 mg/ml).
[form ]

solid
[color ]

Off-white or beige
[Stability:]

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.
Safety DataBack Directory
[Symbol(GHS) ]

GHS hazard pictograms
GHS07
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard InformationBack Directory
[Description]

Leelamine HCl (16496-99-4) is a lysosomotropic, intracellular cholesterol transport inhibitor with potential chemotherapeutic activity. Induces cholesterol accumulation in lysosomal/endosomal cell compartments via inhibition of autophagic flux.1?Induces apoptosis in breast cancer2, melanoma3?and prostate cancer cells4. A selective inducer of cytochrome P450 2B.5?Inhibits pyruvate dehydrogenase kinase (PDK), IC50=9.5 μM.6
[Uses]

Dehydroabiethylamine is a primary amine with high molecular weight; shows a strong antibiotic effect with a broad spectrum of activity against Staphylococcus p.a. (sic), Escherichia coli, Mycobacterium tuberculosis, and Candida albicans.
[IC 50]

CB1
[References]

[1] OMER F KUZU. Leelamine mediates cancer cell death through inhibition of intracellular cholesterol transport.[J]. Molecular Cancer Therapeutics, 2014, 13 7: 1690-1703. DOI:10.1158/1535-7163.mct-13-0868
[2] ANURADHA SEHRAWAT. Cancer-selective death of human breast cancer cells by leelamine is mediated by bax and bak activation.[J]. Molecular Carcinogenesis, 2017, 56 2: 337-348. DOI:10.1002/mc.22497
[3] YU-CHI CHEN. Targeting cholesterol transport in circulating melanoma cells to inhibit metastasis[J]. Pigment Cell & Melanoma Research, 2017, 30 6: 541-552. DOI:10.1111/pcmr.12614
[4] KRISHNA B SINGH  Shivendra V S  Xinhua Ji. Therapeutic Potential of Leelamine, a Novel Inhibitor of Androgen Receptor and Castration-Resistant Prostate Cancer.[J]. Molecular Cancer Therapeutics, 2018, 17 10: 2079-2090. DOI:10.1158/1535-7163.mct-18-0117
[5] JUHEE SIM. Selective induction of hepatic cytochrome P450 2B activity by leelamine in vivo, as a potent novel inducer[J]. Archives of Pharmacal Research, 2014, 38 5: 725-733. DOI:10.1007/s12272-014-0443-0
[6] THOMAS D. AICHER ∗. Triterpene and diterpene inhibitors of pyruvate dehydrogenase kinase (PDK)[J]. Bioorganic & Medicinal Chemistry Letters, 1999, 9 15: Pages 2223-2228. DOI:10.1016/s0960-894x(99)00380-7
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