All Photos(1)

SML1908

Sigma-Aldrich

Syrosingopine

≥95% (HPLC)

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:
Molecular Weight:
666.71
NACRES:
NA.77

Quality Level

assay

≥95% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 10 mg/mL, clear

storage temp.

room temp

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

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.

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Don Benjamin et al.
Science advances, 2(12), e1601756-e1601756 (2016-12-29)
We report that the anticancer activity of the widely used diabetic drug metformin is strongly potentiated by syrosingopine. Synthetic lethality elicited by combining the two drugs is synergistic and specific to transformed cells. This effect is unrelated to syrosingopine's known...
Shumpei Nemoto et al.
Journal of natural products, 84(4), 1283-1293 (2021-04-10)
It is difficult to understand the entire effect of a natural product because such products generally have multiple effects. We propose a strategy to understand these effects effectively by decomposing them with a profile data analysis method we developed. A...
Juan Vélez et al.
Biology, 10(1) (2021-01-21)
Cryptosporidium parvum is an apicomplexan zoonotic parasite recognized as the second leading-cause of diarrhoea-induced mortality in children. In contrast to other apicomplexans, C. ...
Samantha Ames et al.
Oncogene, 39(8), 1710-1723 (2019-11-15)
Tumor cells rely on glycolysis to meet their elevated demand for energy. Thereby they produce significant amounts of lactate and protons, which are exported via monocarboxylate transporters (MCTs), supporting the formation of an acidic microenvironment. The present study demonstrates that...

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