SML1908

Syrosingopine

• Synonym(s): (3β,16β,17α,18β,20α)-18-[[4-[(Ethoxycarbonyl)oxy]-3,5-dimethoxybenzoyl]oxy]-11,17-dimethoxy-yohimban-16-carboxylic acid methyl ester, Methyl reserpate ester of syringic acid ethyl carbonate
• Empirical Formula (Hill Notation): C₃₅H₄₂N₂O₁₁
• CAS Number: 84-36-6
• Molecular Weight: 666.71
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• form: powder
• Quality Level: 100
• color: white to light brown
• solubility: DMSO: 10 mg/mL, clear
• SMILES string: O=C(OC)[C@@H]1[C@]2([H])C[C@@]3([H])C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@]2([H])C[C@H](OC(C6=CC(OC)=C(OC(OCC)=O)C(OC)=C6)=O)[C@H]1OC
• InChI: 1S/C35H42N2O11/c1-7-46-35(40)48-31-26(42-3)12-18(13-27(31)43-4)33(38)47-28-14-19-17-37-11-10-22-21-9-8-20(41-2)15-24(21)36-30(22)25(37)16-23(19)29(32(28)44-5)34(39)45-6/h8-9,12-13,15,19,23,25,28-29,32,36H,7,10-11,14,16-17H2,1-6H3/t19-,23+,25-,28-,29+,32+/m1/s1
• InChI key: ZCDNRPPFBQDQHR-SSYATKPKSA-N

Description

Application

Syrosingopine has been used as a monocarboxylate transporter (MCT) inhibitor

• to study its effects on anti-CD147-induced metabolon disruption in human breast cancer cells
• to study its effects on Cryptosporidium parvum-infected HCT-8 cells
• in orthogonal linear separation analysis (OLSA)-derived decomposed analysis

Biochem/physiol Actions

Syrosingopine is a derivative of reserpine and inhibits monocarboxylate lactate transporters 1 and 4 (MCT1/4).

Syrosingopine is an antihypertensive agent related to reserpine that was found to potentiate the anticancer effects of the antidiabetic agent metformin and phenformin without harmful effects on normal cells. Syrosingopine was also found to potentiate the anticancer activity of mitochondrial electron transport chain (ETC) inhibitors. Its mechanism of action is currently unknown but may involve inhibition of glycolytic enzyme α-enolase rather than its known activity as an inhibitor of vesicular monoamine transporters VMAT1 and VMAT2.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable