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MedKoo Cat#: 527515 | Name: Trodusquemine free base

Description:

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

Trodusquemine, also known as MSI-1436 and MSI-1436C, is a protein tyrosine phosphatase PTP-1B inhibitor potentially for the treatment of type 2 diabetes. Trodusquemine significantly enhanced insulin-stimulated tyrosine phosphorylation of insulin receptor (IR) beta and STAT3, direct targets of PTP1B, in HepG2 cells in vitro and/or hypothalamic tissue in vivo.

Chemical Structure

Trodusquemine free base
Trodusquemine free base
CAS#186139-09-3 (free base)

Theoretical Analysis

MedKoo Cat#: 527515

Name: Trodusquemine free base

CAS#: 186139-09-3 (free base)

Chemical Formula: C37H72N4O5S

Exact Mass: 684.5223

Molecular Weight: 685.07

Elemental Analysis: C, 64.87; H, 10.59; N, 8.18; O, 11.68; S, 4.68

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Related CAS #
186139-09-3 (free base) 1309370-85-1 (phosphate) 1309370-86-2 (lactate)
Synonym
Trodusquemine; MSI-1436; MSI1436; MSI 1436; MSI-1436C; MSI1436C; MSI 1436C; Aminosterol 1436; Aminosterol1436; Aminosterol-1436
IUPAC/Chemical Name
(3R,6R)-6-((3S,5R,7R,8R,9S,10S,13R,14S,17R)-3-((3-((4-((3-aminopropyl)amino)butyl)amino)propyl)amino)-7-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methylheptan-3-yl hydrogen sulfate
InChi Key
WUJVPODXELZABP-FWJXURDUSA-N
InChi Code
InChI=1S/C37H72N4O5S/c1-26(2)34(46-47(43,44)45)13-10-27(3)30-11-12-31-35-32(15-17-37(30,31)5)36(4)16-14-29(24-28(36)25-33(35)42)41-23-9-22-40-20-7-6-19-39-21-8-18-38/h26-35,39-42H,6-25,38H2,1-5H3,(H,43,44,45)/t27-,28-,29+,30-,31+,32+,33-,34-,35+,36+,37-/m1/s1
SMILES Code
CC([C@H](OS(=O)(O)=O)CC[C@H]([C@H]1CC[C@H]2[C@@H]3[C@@H](C[C@H]4C[C@@H](NCCCNCCCCNCCCN)CC[C@@]4([C@H]3CC[C@]12C)C)O)C)C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 685.07 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: Lantz KA, Hart SG, Planey SL, Roitman MF, Ruiz-White IA, Wolfe HR, McLane MP. Inhibition of PTP1B by trodusquemine (MSI-1436) causes fat-specific weight loss in diet-induced obese mice. Obesity (Silver Spring). 2010 Aug;18(8):1516-23. doi: 10.1038/oby.2009.444. PubMed PMID: 20075852. 2: Qin Z, Pandey NR, Zhou X, Stewart CA, Hari A, Huang H, Stewart AF, Brunel JM, Chen HH. Functional properties of Claramine: a novel PTP1B inhibitor and insulin-mimetic compound. Biochem Biophys Res Commun. 2015 Feb 27;458(1):21-7. doi: 10.1016/j.bbrc.2015.01.040. PubMed PMID: 25623533. 3: Salmi C, Loncle C, Vidal N, Laget M, Letourneux Y, Brunel JM. Antimicrobial activities of 3-amino- and polyaminosterol analogues of squalamine and trodusquemine. J Enzyme Inhib Med Chem. 2008 Dec;23(6):860-5. doi: 10.1080/14756360701809910 . PubMed PMID: 19005944. 4: Djouhri-Bouktab L, Vidal N, Rolain JM, Brunel JM. Synthesis of new 3,20-bispolyaminosteroid squalamine analogues and evaluation of their antimicrobial activities. J Med Chem. 2011 Oct 27;54(20):7417-21. doi: 10.1021/jm200506x. PubMed PMID: 21905738. 5: Roitman MF, Wescott S, Cone JJ, McLane MP, Wolfe HR. MSI-1436 reduces acute food intake without affecting dopamine transporter activity. Pharmacol Biochem Behav. 2010 Nov;97(1):138-43. doi: 10.1016/j.pbb.2010.05.010. PubMed PMID: 20478327; PubMed Central PMCID: PMC2945616. 6: Salmi C, Loncle C, Vidal N, Letourneux Y, Brunel JM. New stereoselective titanium reductive amination synthesis of 3-amino and polyaminosterol derivatives possessing antimicrobial activities. Eur J Med Chem. 2008 Mar;43(3):540-7. PubMed PMID: 17566609. 7: Pandey NR, Zhou X, Zaman T, Cruz SA, Qin Z, Lu M, Keyhanian K, Brunel JM, Stewart AF, Chen HH. LMO4 is required to maintain hypothalamic insulin signaling. Biochem Biophys Res Commun. 2014 Jul 18;450(1):666-72. doi: 10.1016/j.bbrc.2014.06.026. PubMed PMID: 24937445. 8: Krishnan N, Tonks NK. Anxious moments for the protein tyrosine phosphatase PTP1B. Trends Neurosci. 2015 Aug;38(8):462-5. doi: 10.1016/j.tins.2015.06.006. PubMed PMID: 26166619; PubMed Central PMCID: PMC4530058. 9: Krishnan N, Koveal D, Miller DH, Xue B, Akshinthala SD, Kragelj J, Jensen MR, Gauss CM, Page R, Blackledge M, Muthuswamy SK, Peti W, Tonks NK. Targeting the disordered C terminus of PTP1B with an allosteric inhibitor. Nat Chem Biol. 2014 Jul;10(7):558-66. doi: 10.1038/nchembio.1528. PubMed PMID: 24845231; PubMed Central PMCID: PMC4062594. 10: Pandey NR, Zhou X, Qin Z, Zaman T, Gomez-Smith M, Keyhanian K, Anisman H, Brunel JM, Stewart AF, Chen HH. The LIM domain only 4 protein is a metabolic responsive inhibitor of protein tyrosine phosphatase 1B that controls hypothalamic leptin signaling. J Neurosci. 2013 Jul 31;33(31):12647-55. doi: 10.1523/JNEUROSCI.0746-13.2013. PubMed PMID: 23904601. 11: Fan G, Lin G, Lucito R, Tonks NK. Protein-tyrosine phosphatase 1B antagonized signaling by insulin-like growth factor-1 receptor and kinase BRK/PTK6 in ovarian cancer cells. J Biol Chem. 2013 Aug 23;288(34):24923-34. doi: 10.1074/jbc.M113.482737. PubMed PMID: 23814047; PubMed Central PMCID: PMC3750187. 12: Cho H. Protein tyrosine phosphatase 1B (PTP1B) and obesity. Vitam Horm. 2013;91:405-24. doi: 10.1016/B978-0-12-407766-9.00017-1. Review. PubMed PMID: 23374726. 13: Scott LM, Chen L, Daniel KG, Brooks WH, Guida WC, Lawrence HR, Sebti SM, Lawrence NJ, Wu J. Shp2 protein tyrosine phosphatase inhibitor activity of estramustine phosphate and its triterpenoid analogs. Bioorg Med Chem Lett. 2011 Jan 15;21(2):730-3. doi: 10.1016/j.bmcl.2010.11.117. PubMed PMID: 21193311; PubMed Central PMCID: PMC3034307. 14: Ahima RS, Patel HR, Takahashi N, Qi Y, Hileman SM, Zasloff MA. Appetite suppression and weight reduction by a centrally active aminosterol. Diabetes. 2002 Jul;51(7):2099-104. PubMed PMID: 12086938. 15: Shu Y, Jones SR, Kinney WA, Selinsky BS. The synthesis of spermine analogs of the shark aminosterol squalamine. Steroids. 2002 Mar;67(3-4):291-304. PubMed PMID: 11856553. 16: Zasloff M, Williams JI, Chen Q, Anderson M, Maeder T, Holroyd K, Jones S, Kinney W, Cheshire K, McLane M. A spermine-coupled cholesterol metabolite from the shark with potent appetite suppressant and antidiabetic properties. Int J Obes Relat Metab Disord. 2001 May;25(5):689-97. PubMed PMID: 11360152.

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