Cytotoxicity of Hydrazones of Morpholine Bearing Mannich Bases .

Hydrazone kháng T47D

From Wikipedia, the free encyclopedia

Structure of the hydrazone functional group

Hydrazones are a class of organic compounds with the structure R
1R
2C=NNH
2.^[1] They are related to ketones and aldehydes by the replacement of the oxygen with the NNH
2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.^[2][3]

Contents

  [hide] 

• 1Uses
• 2Reactions
• 3N,N′-dialkylhydrazones
• 4Gallery
• 5See also
• 6References

Uses[edit]

The formation of aromatic hydrazone derivatives is used to measure the concentration of low molecular weight aldehydes and ketones, e.g. in gas streams. For example, dinitrophenylhydrazine coated onto a silica sorbent is the basis of an adsorption cartridge. The hydrazones are then eluted and analyzed by HPLC using a UVdetector.

The compound carbonyl cyanide-p-trifluoromethoxyphenylhydrazone (abbreviated as FCCP) is used to uncouple ATP synthesis and reduction of oxygen in oxidative phosphorylation in molecular biology. Phenylhydrazine reacts with glucose to form an osazone.

Hydrazone-based coupling methods are used in medical biotechnology to couple drugs to targeted antibodies (see ADC), e.g. antibodies against a certain type of cancer cell. The hydrazone-based bond is stable at neutral pH (in the blood), but is rapidly destroyed in the acidic environment of lysosomes of the cell. The drug is thereby released in the cell, where it exerts its function.^[4]

In aqueous solution, aliphatic hydrazones are 10²- to 10³-fold more sensitive to hydrolysis than analogous oximes.^[5]

Reactions[edit]

Hydrazones are reactants in hydrazone iodination, the Shapiro reaction and the Bamford-Stevens reaction to vinyl compounds. A hydrazone is an intermediate in the Wolff–Kishner reduction. Hydrazones can also be synthesized by the Japp–Klingemann reaction via β-keto-acids or β-keto-esters and aryl diazonium salts. The mechanochemical process was used recently as a green one to synthesize pharmaceutically attractive phenol hydrazones.^[6] Hydrazones are converted to azines when used in the preparation of 3,5-disubstituted 1H-pyrazoles,^[7] a reaction also well known using hydrazine hydrate.^[8][9]

N,N′-dialkylhydrazones[edit]

Main article: Enders SAMP/RAMP hydrazone alkylation reaction

In N,N′-dialkylhydrazones^[10] the C=N bond can be hydrolysed, oxidised and reduced, the N-N bond can be reduced to the free amine. The carbon atom if the C=N bond can react with organometallic nucleophiles. The alpha-hydrogen atom is more acidic by 10 orders of magnitude compared to the ketone and therefore more nucleophilic. Deprotonation with for instance LDA gives an azaenolate which can be alkylated by alkyl halides, a reaction pioneered by E.J. Corey and Dieter Enders in 1978.^[11][12] In asymmetric synthesis SAMP and RAMP are two chiral hydrazines that act as chiral auxiliary with a chiral hydrazone intermediate.^[13][14][15]

Gallery[edit]

• Hydrazones
• 

  Benzophenone hydrazone, an illustrative hydrazone
 
• 

  Carbonyl cyanide m-chlorophenyl hydrazone
 
• 

  Gyromitrin(Acetaldehyde methylformylhydrazone), a toxin
 
• 

  Dihydralazine, an antihypertensive drug

See also[edit]

• Azo compound
• Imine
• Nitrosamine
• Hydrogenation of carbon–nitrogen double bonds

Ethylacetate Extract of Zanthoxylum acanthopodium DC. Fruit Agains

Andaliman-Zanthoxylum acanthopodium kháng T47D

From Wikipedia, the free encyclopedia

  (Redirected from Zanthoxylum acanthopodium)

This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (December 2014) (Learn how and when to remove this template message)

Zanthoxylum acanthopodium
Habitus
Scientific classification
Kingdom:	Plantae
(unranked):	Angiosperms
(unranked):	Eudicots
(unranked):	Rosids
Order:	Sapindales
Family:	Rutaceae
Genus:	Zanthoxylum
Species:	Z. acanthopodium
Binomial name
Zanthoxylum acanthopodium DC.[1]

Seeds

Andaliman (Zanthoxylum acanthopodium) is a species of flowering plant in the citrus family, Rutaceae. Its range includes southern China (western Guangxi Guizhou, Sichuan, Tibet Autonomous Region, and Yunnan), Bangladesh, Bhutan, northern India(Arunachal Pradesh, Assam, Manipur, Meghalaya, Mizoram, Nagaland, Sikkim, Uttar Pradesh, and West Bengal), Nepal, Laos, Burma, northern Thailand Vietnam, Indonesia (northern Sumatran highlands), and Peninsular Malaysia.^[1]

Much like the closely related Sichuan pepper (Z. piperitum), the seed pericarps are used as spices in cooking and have a similar tongue-numbing characteristic. However, in cooking, the flavour of andaliman has lemon-like notes (similar to those of lemon-grass) as well as a hint of the aromatic pandan leaf.

Phytoestrogens and breast cancer: Effects of fisetin on T47D cells

Fisetin kháng T47D

From Wikipedia, the free encyclopedia

Fisetin

Names
IUPAC name 2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one
Other names Cotinin (not to be confused with Cotinine) 5-Deoxyquercetin Superfustel Fisetholz Fietin Fustel Fustet Viset Junger fustik
Identifiers
CAS Number	528-48-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:42567
ChemSpider	4444933
DrugBank	DB07795
ECHA InfoCard	100.007.669
IUPHAR/BPS	5182
KEGG	C10041
PubChem CID	5281614
InChI[show]
SMILES[show]
Properties
Chemical formula	C15H10O6
Molar mass	286.2363 g/mol
Density	1.688 g/mL
Melting point	330 °C (626 °F; 603 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

Fisetin (7,3′,4′-flavon-3-ol), is a plant polyphenol from the flavonoid group. It can be found in many plants, where it serves as a colouring agent. It is also found in many fruits and vegetables, such as strawberries, apples, persimmons, onions and cucumbers.^[1] Its chemical formula was first described by Austrian chemist Josef Herzig in 1891.^[2]

The biological activity of fisetin has been studied in many laboratory assays; like other polyphenols it has many activities.

Contents

  [hide] 

• 1Biological sources
  • 1.1Biosynthesis
• 2Research
• 3References

Biological sources[edit]

Fisetin can be found in a wide variety of plants. It is found in Eudicotyledons, such as trees and shrubs in the family Fabaceae, such as the acacias Acacia greggii^[3] and Acacia berlandieri,^[3] the parrot tree (Butea frondosa), the honey locust (Gleditsia triacanthos), members of the family Anacardiaceae such as the Quebracho colorado and species of the genus Rhus, which contains the sumacs.^[4] Along with myricetin, fisetin provides the color of the traditional yellow dye young fustic, which was extracted from the Eurasian smoketree (Rhus cotinus). Many fruits and vegetables also contain fisetin,^[5] including strawberries^[6][7] apples,^[7] and grapes.^[7][8] Fisetin can be extracted from fruit and herbal sources in juices, wines,^[9] and infusions such as teas.^[8] It is also found in Monocotyledons such as onions.^[7] It is also present in Pinophyta species such as the yellow cypress (Callitropsis nootkatensis).

Biosynthesis[edit]

Fisetin is a polyphenol, which is a flavonoid subgroup. Flavonoid synthesis begins with the phenylpropanoid pathway, in which phenylalanine, an amino acid, is transformed into 4-coumaroyl-CoA. This is the compound that enters the flavonoid biosynthesis pathway. Chalcone synthase, the first enzyme of this pathway, produces chalcone from 4-coumaroyl-CoA. All flavonoids are derived from this chalcone backbone (this family being the so-called chalconoids). The activity of different enzymes, including isomerases and hydroxylases, alter the backbone depending on the subclass of the flavonoid being produced. Transferases help control changes in the flavonoid’s solubility and reactivity by catalyzing the addition of things such as methyl groups and sugars. This allows for controlled fluctuations in physiological activities.^[10]

Flavonoid biosynthesis gene regulation occurs through the interaction of different transcription factors. Depending on the combination of transcription factor interactions, the structural genes involved in flavonoid biosynthesis are expressed in specific locations of the plant and at specific times. Many myeloblastosis (MYB) transcription factors have been identified in a variety of fruits and plants, including strawberries, maize, and arabidopsis, as being important in the regulation of flavonoid biosynthesis and accumulation. These transcription factors continue to be studied in plant model organisms such as maize and Arabidopsis.^[10]

The environment of the plant has also been shown to affect the flavonoid biosynthesis pathway. Shorter wavelengths of light, ranging from blue to UV light, allow for higher production and accumulation of flavonoids in fruits. These wavelengths activate enzymes that are involved in the phenylpropanoid and flavonoid biosynthesis pathways, stimulating the production of flavonoids. The level of stimulation can vary between individual fruits.^[11]

Research[edit]

Fisetin, like other polyphenols such as resveratrol, is a sirtuin-activating compound and has been shown in laboratory studies to extend the life of simple organisms like yeast, worms, and flies.^[12] Like the other compounds, it has also been shown to be reactive in many different assays of biological activities, raising the possibility that any drug generated from fisetin would have too many side effects to be useful.^[12][13]

Fisetin has shown anti-cancer activity in studies on cells and model animals conducted in laboratories, and appears to block the PI3K/AKT/mTOR pathway.^[14] In lab studies it also has been shown to be an anti-proliferative agent, interfering with the cell cycle in several ways.^[15] Fisetin, like some other flavonoids, has been found in lab studies to be a topoisomerase inhibitor, which may turn out to be a carcinogenic activity or an anti-cancer activity - further research is needed.^[16]

In studies conducted on cells in a laboratory, fisetin inhibits the activity of several pro-inflammatory cytokines, including tumor necrosis factor alpha, interleukin 6, and Nuclear factor kappa B.^[15] It has also been shown in lab studies to upregulate glutathione, an endogenous antioxidant.^[15][17] Fisetin also has direct activity as a reducing agent, chemically reacting with reactive oxygen species to neutralize them.^[17] Based on lab studies, it appears that fisetin lodges in cell membranes and prevents oxidative damage to lipids in the cell membrane.^[17] Fisetin, like other flavonoids, has a planar structure, with multiple carbon rings. Fisetin is able to scavenge free radicals as a result of its electron donating capacity, which is due to the presence of two hydroxyl groups on one ring and a hydroxyl group on another ring.^[17]

In vitro screening has identified fisetin as an antimitotic compound.^[18]