CAS 153-18-4 Rutin - ADC / BOC Sciences

Rutin - CAS 153-18-4 Catalog number: BADC-00316

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Rutin is colored brown by tobacco enzyme under experimental conditions. In medicine, it has been used as an auxiliary drug and nutritional supplement for the treatment of cardiovascular system diseases. Because it is not toxic to the human body, it can also be used as an antioxidant and natural edible yellow pigment in the food industry.

Category

ADCs Cytotoxin

Product Name

Rutin

CAS

153-18-4

Catalog Number

BADC-00316

Molecular Formula

C27H30O16

Molecular Weight

610.53

Ordering Information

Catalog Number	Size	Price	Stock	Quantity
BADC-00316	1 kg	$289	In stock

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Products Information
Reference Reading

Description

Synonyms

Rutoside; Phytomelin; Quercetin 3-rutinoside

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

Canonical SMILES

CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O

InChI

InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1

InChIKey

IKGXIBQEEMLURG-NVPNHPEKSA-N

Density

1.82 g/cm3

Solubility

DMSO (slightly, heated), methanol (slightly)

Melting Point

189-191°C

LogP

-2.02

In Vitro

The astrocyte primary cultures and astrocyte/microglia mixed primary cell cultures derived from newborn rat cortical brain was used. The cultures were treated for 24 h with rutin (50 or 100 micromol/L) or vehicle (0.5% dimethyl sulfoxide). Mitochondrial function on glial cells was not evidenced by the MTT test. However, an increased lactate dehydrogenase activity was detected in the culture medium of both culture systems when treated with 100 micromol/L rutin, suggesting loss of cell membrane integrity. Astrocytes exposed to 50 micromol/L rutin became reactive as revealed by glial fibrillary acidic protein (GFAP) overexpression and showed a star-like phenotype revealed by Rosenfeld's staining. The number of activated microglia expressing OX-42 increased in the presence of rutin. A significant increase of nitric oxide (NO) was observed only in mixed cultures exposed to 100 micromol/L rutin. Enhanced TNFalpha release was observed in astrocyte primary cultures treated with 100 micromol/L rutin and in mixed primary cultures treated with 50 and 100 micromol/L, suggesting different sensitivity of both activated cell types.

In Vivo

The intraperitoneal injection of rutin at 30 mg/kg, 3X/week, significantly reduced the growth of the TNBC MDA-MB-231/GFP orthotopic xenograft in nude mouse model. These results clearly designate the functional dietary flavonoid rutin as a potential lead for the prevention and control of c-Met-dependent breast malignancies.

Clinical Trial Information

NCT Number	Condition Or Disease	Phase	Start Date	Sponsor	Status
NCT04161872	Hyperuricemia	Phase 4	2020-11-10	University of Pavia	Completed
NCT04955145	End Stage Renal Disease	Phase 3	2021-07-19	Ain Shams University	Recruiting
NCT03437902	Type 2 Diabetes Mellitus	Phase 2, Phase 3	2018-05-16	Ain Shams University	Completed
NCT04669977	Chemotherapy-induced Peripheral Neuropathy	Not Applicable	2020-12-17	Taipei Medical University	Recruiting
NCT05038410	Osteoarthritis	Not Applicable	2021-09-09	Mucos Pharma GmbH & Co. KG	Recruiting

Application

ADCs Cytotoxin

Appearance

Pale-Yellow Solid

Purity

>95% (HPLC)

Shipping

Room temperature

Storage

Dark, dry and cool place

Pictograms

Irritant

Signal Word

Warning

1.Therapeutic effect of ozone and rutin on adriamycin-induced testicular toxicity in an experimental rat model.

Salem EA1, Salem NA2, Hellstrom WJ3. Andrologia. 2016 May 2. doi: 10.1111/and.12603. [Epub ahead of print]

To evaluate the cytoprotective effects of rutin, ozone and their combination on adriamycin (ADR)-induced testicular toxicity, 50 male albino rats were classified into five groups of ten animals each as follows: placebo group; ADR group; ADR + rutin group; ADR + ozone group and ADR + rutin + ozone group. Sperm functions, testosterone (T), luteinising hormone (LH), follicle stimulating hormone (FSH), testicular enzymes, oxidant/antioxidant status, C-reactive protein, monocyte chemoattractant proteins-1 and leukotriene B4 were determined. After ADR injection, a decline in sperm functions was observed. FSH and LH levels were increased, T level and testicular enzymes were decreased, significant enhancement in oxidative stress with subsequent depletion in antioxidants was detected and inflammatory markers were significantly elevated. Treatment with rutin and/or ozone, however, improved the aforementioned parameters. Ozone therapy alone almost completely reversed the toxic effects of ADR and restored all parameters to normal levels.

2.Effects of rutin on the redox reactions of hemoglobin.

Lu N1, Ding Y2, Yang Z3, Gao P4. Int J Biol Macromol. 2016 Apr 25;89:175-180. doi: 10.1016/j.ijbiomac.2016.04.066. [Epub ahead of print]

Flavonoids are widely used to attenuate oxidative damage in vitro and in vivo. In this study, we investigated the influence of rutin (quercetin-3-rhamnosylglucoside) on hemoglobin (Hb)- dependent redox reactions, i.e. oxidative stability of Hb and its cytotoxic ferryl intermediate. It was found that rutin induced generation of H2O2, which in turn oxidized Hb rapidly. Meanwhile, rutin exhibited anti-oxidant effect by effectively reducing ferryl intermediate back to ferric Hb at physiological pH. In comparison with quercetin, rutin had stronger capability on reducing ferryl species while lesser pro-oxidant effect on H2O2 generation, thus it exhibited more protective effect on H2O2-induced Hb oxidation. Circular dichroism spectrum showed no significant change in the secondary structure of Hb after flavonoid addition, while molecular docking revealed different binding modes of quercetin and rutin with Hb. These results might provide new insights into the potential nutritional and physiological implications of rutin and quercetin with redox active heme proteins regarding their ani- and pro-oxidant effects.

3.Sensitive electrochemical detection of rutin and isoquercitrin based on SH-β-cyclodextrin functionalized graphene-palladium nanoparticles.

Liu Z1, Xue Q1, Guo Y2. Biosens Bioelectron. 2016 Apr 22. pii: S0956-5663(16)30330-X. doi: 10.1016/j.bios.2016.04.056. [Epub ahead of print]

In this study, a sensitive electrochemical method based on thio-β-cyclodextrin functionalized graphene/palladium nanoparticles (SH-β-CD-Gr/PdNPs) was developed to detect rutin and isoquercitrin, respectively. The obtained SH-β-CD-Gr/PdNPs were characterized by UV-vis spectroscopy, Fourier transform infrared spectroscopy, transmission electron microscopy and X-ray photoelectron spectroscopy. The results confirm that SH-β-CD and PdNPs were successfully deposited on the surface of graphene nanosheets (GNs). The peak currents of rutin and isoquercitrin on the SH-β-CD-Gr/PdNPs modified glassy carbon electrode (GCE) are dramatically increased compared with that on the bare GCE and SH-β-CD-Gr/GCE. It indicated that the nanocomposite integrated the excellent electric conductivity and electrocatalytic activity of graphene and PdNPs, as well as the host-guest recognition and enrichment ability of SH-β-CD. Under optimum conditions, differential pulse voltammetry (DPV) was used to measure the peak currents of the two drugs.

4.Rutin ameliorates cisplatin-induced reproductive damage via suppression of oxidative stress and apoptosis in adult male rats.

Aksu EH1, Kandemir FM2, Özkaraca M3, Ömür AD1, Küçükler S2, Çomaklı S3. Andrologia. 2016 Apr 23. doi: 10.1111/and.12593. [Epub ahead of print]

Cisplatin (CP) treatment causes damage in the male reproductive system. Rutin (RUT) is a naturally occurring flavonoid glycoside that has antioxidant and anti-inflammatory properties. This study aimed to investigate effects of RUT against cisplatin-induced reproductive toxicity in male rats. Twenty-one adult male Sprague Dawley rats were used. The control group received physiological saline with oral gavage during 14 days, and physiological saline was injected intraperitoneally (IP) in 10th days of study. CP Group received physiological saline during 14 days, and 10 mg kg-1 CP was injected IP in 10th day. RUT + CP group received RUT (150 mg kg-1 ) during 14 days, and 10 mg kg-1 CP was injected IP in 10th day. Spermatological parameters (including motility, cauda epididymal sperm density, dead sperm percentage and morphological sperm abnormalities), biochemical (MDA, GSH, GSH-px, SOD and CAT), histological (H&E dye) and immunochemistry evaluations of testicles were evaluated.