Skip to Content
MilliporeSigma
All Photos(1)

Documents

SML1908

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C35H42N2O11
CAS Number:
84-36-6
Molecular Weight:
666.71
UNSPSC Code:
12352200
NACRES:
NA.77

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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 8

1 of 8

5-(N,N-Hexamethylene)amiloride

Sigma-Aldrich

A9561

5-(N,N-Hexamethylene)amiloride

α-Cyano-4-hydroxycinnamic acid ≥98% (TLC), powder

Sigma-Aldrich

C2020

α-Cyano-4-hydroxycinnamic acid

1,1-Dimethylbiguanide hydrochloride 97%

Sigma-Aldrich

D150959

1,1-Dimethylbiguanide hydrochloride

Methylcyclopentane 97%

Sigma-Aldrich

M39407

Methylcyclopentane

3,5-Dihydroxybenzoic acid 97%

Sigma-Aldrich

D110000

3,5-Dihydroxybenzoic acid

(+)-Etomoxir sodium salt hydrate ≥98% (HPLC), powder

Sigma-Aldrich

E1905

(+)-Etomoxir sodium salt hydrate

2-Deoxy-D-glucose ≥98% (GC), crystalline

Sigma-Aldrich

D8375

2-Deoxy-D-glucose

Metformin hydrochloride Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1084

Metformin hydrochloride

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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service