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Merck

SML1908

Syrosingopine

monocarboxylate lactate transporters 1 and 4 inhibitor, powder

Sinónimos:

(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

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Fórmula empírica (notación de Hill):
C35H42N2O11
Número CAS:
Peso molecular:
666.71
UNSPSC Code:
12352200
NACRES:
NA.77
Form:
powder
Servicio técnico
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Nombre del producto

Syrosingopine,

form

powder

Quality Segment

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 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.


Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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