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Merck

SML1908

Sigma-Aldrich

Syrosingopine

别名:

(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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About This Item

经验公式(希尔记法):
C35H42N2O11
CAS号:
分子量:
666.71
分類程式碼代碼:
12352200
NACRES:
NA.77

形狀

powder

品質等級

顏色

white to light brown

溶解度

DMSO: 10 mg/mL, clear

SMILES 字串

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 密鑰

ZCDNRPPFBQDQHR-SSYATKPKSA-N

應用

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

生化/生理作用

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.

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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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

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