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D0817

Sigma-Aldrich

(−)-Deguelin

>98% (HPLC), powder

Sinônimo(s):

(7aS,13aS)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6′,5′-e]pyran-7(7aH)-one

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About This Item

Fórmula empírica (Notação de Hill):
C23H22O6
Número CAS:
522-17-8
Peso molecular:
394.42
Número MDL:
MFCD01740600
Código UNSPSC:
12352200
ID de substância PubChem:
329798641
NACRES:
NA.77

Ensaio

>98% (HPLC)

Formulário

powder

atividade óptica

[α]/D -70 to -80°, c = 0.2 in methanol

cor

white to beige

pf

85-87 °C (lit.)

solubilidade

DMSO: 10 mg/mL, clear

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

COc1cc2OC[C@H]3Oc4c(ccc5OC(C)(C)C=Cc45)C(=O)[C@H]3c2cc1OC

InChI

1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1

chave InChI

ORDAZKGHSNRHTD-UXHICEINSA-N

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Aplicação

(−)-Deguelin has been used as:
  • a nicotinamide adenine dinucleotide hydrogen (NADH) dehydrogenase (Complex I) inhibitor to study its effects on mitochondrial respiratory inhibition in human hepatocarcinoma cells (HepG2) and human renal proximal tubule epithelial cells (RPTECs)
  • an antiviral compound to study inhibitory effects on human cytomegalovirus (HCMV)-infected human foreskin fibroblast (HFF) cells
  • an analytical standard in high-performance liquid chromatography (HPLC)

Ações bioquímicas/fisiológicas

Deguelin is a natural rotenoid compound present abundantly in barks, leaves, seeds, and roots of the plants belonging to the Leguminosae family. Deguelin has been studied as a therapeutic agent against the skin, lung cancer, and mammary tumorigenesis.
Inhibitor of activated Akt. Does not affect MAPK, ERK1/2, or JNK. Anticancer, chemoprotective agent.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

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Certificados de análise (COA)

Lot/Batch Number
026M4755V
076M4742V
045M4736V
014M4713V
100M4603V

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Rahel Sarah Varughese et al.
Cancer, 125(11), 1789-1798 (2019-04-02)
Deguelin is a rotenoid compound that exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants. An analysis of evidence from both in vitro and in vivo studies suggests that deguelin displays potent anticancer
Bin-Chuan Ji et al.
Oncology reports, 27(4), 959-964 (2012-01-10)
It has been shown that deguelin, one of the compounds of rotenoids from flavonoid family, induced cytotoxic effects through induction of cell cycle arrest and apoptosis in many types of human cancer cell lines, but deguelin-affected DNA damage and repair
Zhao-hui Chu et al.
Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine, 9(5), 533-538 (2011-05-14)
To study the effects of deguelin on proliferation and apoptosis of human breast cancer cell line MCF-7 and on phosphatidylinositol 3-kinase/protein kinase B (PI3K/Akt) signaling pathway. After treatment with 0, 1, 5, 10, 15 and 20 μmol/L of deguelin for
Dong-Jo Chang et al.
Journal of medicinal chemistry, 55(24), 10863-10884 (2012-11-29)
Deguelin exhibits potent apoptotic and antiangiogenic activities in a variety of transformed cells and cancer cells. Deguelin also exhibits potent tumor suppressive effects in xenograft tumor models for many human cancers. Our initial studies confirmed that deguelin disrupts ATP binding
Vijayalakshmi Thamilselvan et al.
International journal of cancer, 129(12), 2916-2927 (2011-04-08)
Activation of survival pathways has been associated with chemoresistance and progression of androgen independence which places a major obstacle to successful treatment of metastatic prostate cancer. Deguelin, a rotenoid isolated from Mundulea sericea, has an anticancer effect against several types
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