Fatty Acid.

Transcript

1 Address:800 S Wineville Avenue, Ontario, CA 91761,USA Website: USA: tech@aladdin-e.com EU: eutech@aladdin-e.com Asia Pacific: cntech@aladdin-e.com Fatty Acid Proliferatively active cells require fatty acids for functions such as membrane generation, protein modification, and bioenergetic requirements. These fatty acids are derived either from dietary sources or are synthesized by the cell. While most non-transformed cells rely on dietary-derived fatty acids to meet their biosynthetic and bioenergetic needs, many cancer cells exhibit a lipogenic phenotype with the upregulation of many of the proteins involved in de novo fatty acid synthesis. In particular, overexpression of the multi-enzyme complex fatty acid synthase (FASN) is common to many tumor cells and is often associated with poor prognosis. 1 In addition to increased FASN activity, oncogenic progression is often associated with the increased activity and expression of many enzymes involved in fatty acid synthesis such as acetyl-coa carboxylase (ACC) and ATP citrate lyase (ACL). 1,2 Fatty acid synthesis requires acetyl-coa generated from citrate produced by the TCA cycle or from cytoplasmic α-ketoglutarate. Excess pyruvate generated by enhanced glycolysis is converted to acetyl-coa in the mitochondria through the activity of pyruvate dehydrogenase and shuttled to the cytoplasm as citrate via the citrate shuttle. 1 Glutamine metabolism can produce citrate either through the TCA cycle or by the reductive carboxylation of cytoplasmic α-ketoglutarate to citrate by isocitrate dehydrogenase-1 (IDH1).The latter pathway is favored by cells with defects in mitochondrial oxidation, cells growing in hypoxic conditions, or those exhibiting pseudohypoxia due to activated HIF signaling. 3,4 Citrate is converted back to acetyl-coa and oxaloacetate in a reaction catalyzed by ACL. Cytoplasmic acetyl-coa is then carboxylated to malonyl-coa through ACC, the rate-limiting step for long-chain fatty acid synthesis. Malonlyl-CoA and acetyl- CoA are converted to palmitate by FASN. 1,2 Oncogenic signaling contributes both directly and indirectly to the upregulation of fatty acid synthesis pathways. The increased expression and activity of ACL, ACC, and FASN in multiple cancer types suggests this pathway may contribute to increased survival and proliferation of tumor cells. Both PI3K/AKT and MAPK signaling contributes to the increased expression of FASN and other lipogenic proteins, and ACL is a direct target of AKT phosphorylation. 1 Inhibition of ACL activity in glycolytically-active tumor cells resulted in their decreased proliferation and survival. 5 Similarly, the RNAimediated knockdown of ACC resulted in decreased proliferation and survival of certain tumor cells. 1,6 Accumulating evidence suggests 1

2 that FASN, in addition to its role in fatty acid synthesis, is a metabolic oncogene. Ectopic expression of FASN in non-transformed prostrate cells protected the cells from apoptosis, and the injection of transgenic FASN-expressing prostrate cells in a xenograft model resulted in increased neoplasia when compared to controls. Small molecule inhibitors of FASN, such as Cerulenin and C75, preferentially promote apoptosis of cancer cells compared to normal cells. In addition, many naturally occurring dietary compounds and polyphenols such as catechin, epigallocatechin, and luteolin are being investigated as potential fatty acid synthesis inhibitors. 6 References: 1. Menedez, J. A. and Lupu, R. Fatty Acid Synthase and the Lipogenic Phenotype in Cancer Pathogenesis. Nature Rev. Cancer, 7, (2007). 2. Mashima, T. et al. De Novo Fatty-Acid Synthesis and Related Pathways as Molecular Targets for Cancer Therapy. Br. J. Cancer, 100, (2009). 3. Metallo, C. M. et al. Reductive Glutamine Metabolism by IDH1 Mediates Lipogenesis Under Hypoxia. Nature. 481, (2012). 4. Mullen, A. R. et al. Reductive Carboxylation Supports Growth in Tumour Cells With Defective Mitochondria. Nature. 481, (2012). 5. Hatzivassiliour, G. et al. ATP Citrate Lyase Inhibition Can Suppress Tumor Cell Growth. Cancer Cell. 8, (2005). 6. Flavin, R. et al. Fatty Acid Synthase as a Potential Therapeutic Target in Cancer. Future Oncol. 6, (2010). For more information and a complete list of the related products, please click: Aladdin The related products Item No. Product Name Specification CAS Pkg. A (+)-Abscisic acid 98% (HPLC) mg, 1g A (+)-Abscisic acid 95% (HPLC) mg, 1g A (+)-Abscisic acid 90% (HPLC) g A Allantoin 98% g, 100g, 500g, 1kg A Acetophenone AR, 98.0% (GC) ml A Acetophenone CP,98% ml A Acetophenone GR, 99.0% (GC) ml, 2.5L, 10L A γ-aminobutyric acid 99% g, 25g, 100g, 500g A N-Acetyl-L-Cysteine 99% g, 100g, 500g A N-Acetyl-L-Cysteine USP, EP, 98.5% kg A N-Acetyl-L-Cysteine For cell culture, 99.0% g, 100g A Apigenin 98.0% (HPLC) mg, 100mg, 1g A trans-β-apo-8 -carotenal 96% mg, 1g A Arbutin 99% g, 25g, 100g A Amygdalin 97% g, 5g, 25g A Aloin 97% mg A Anthracene 96% g, 100g, 500g, 2.5kg A Anthracene 99.0% (GC) g, 100g, 500g A Anthracene 98% g, 100g, 500g, 2.5kg, 5kg A Adenine 98% g, 25g, 100g, 500g A Adenine 99.5% (HPLC) g, 25g, 100g, 500g A Acacia USP g, 2.5kg, 25kg A Acacia g, 2.5kg, 25kg 2

3 A (-)-Anabasine 94% mg, 500mg A Acetoin 97% g, 100g, 500g A Acetoin Analytical Standards g A ( )-Arctigenin 98% (HPLC) mg A Angoroside C 98% mg A Artemisinin 98% g, 25g A Arachidic acid 99% g, 5g, 25g A Arachidic acid 80% g, 500g A Alginic acid from brown algae CP g, 500g, 2.5kg A Alginic acid from brown algae USP g A Alliin Analytical Standards,98.5% mg, 25mg A Alliin 90% mg, 100mg, 1g A Aloe-emodin 95% mg, 100mg A Ammothamnine 98% mg A Asiatic acid 98% g, 5g, 25g A (+)-Anabasine hydrochloride 96% mg B Benzyl benzoate CP,98.0% ml B Benzyl benzoate >99.0%(GC) ml, 500ml, 2.5L, B D-Biotin 98% g, 5g, 25g B Betaine monohydrate 99% g, 500g B Baicalin 98% mg, 500mg B Benzyl acetate 99% g, 1kg B Baicalin 90% g, 5g, 25g B Baicalin 95% g, 5g B Butyl benzoate 98% ml, 500ml B Butyl oleate ~70% ml, 500ml B bees wax USP 250g B bees wax C 250g B bees wax C 250g B Betaine Hydrochloride 99% g, 500g, 2.5kg B Benzaldehyde propylene glycol acetal 98% ml, 500ml B (-)-Bilobalide from Ginkgo biloba leaves 98% mg, 100mg C Crotaline 95% mg, 250mg, 1g C Cryptotanshinone 98% mg, 250mg C Crotonic acid 98% g, 500g, 2.5kg C L(-)-Carnitine 98% g, 25g, 100g C L(-)-Carnitine Analytical Standards,99% mg C Creatine monohydrate BR g, 100g, 500g C Creatine 98% g, 100g, 500g C (±)-Catechin hydrate 96% mg, 500mg C Celastrol 98% mg C (+)-Catechin Hydrate 98% g, 5g C Chondroitin sulfate sodium salt from shark cartilage 95% mg, 1g, 5g, 25g C Cytisine 98% mg, 100mg, 500mg C (S)-(+)-Carvone 97% ml, 100ml C Caffeic acid 98% g, 25g C Caffeic acid 99% g, 25g C trans-cinnamic acid CP,98% g, 500g C trans-cinnamic acid AR,99% g, 100g, 500g C p-coumaric acid 98% g, 25g, 100g, 500g C p-coumaric acid Analytical Standards, 99% mg C Citrate AR, 99.5% (T) g, 1kg, 20kg 3

4 C Citrate CP, 99.0% (T) g C Citrate For cell culture,97.0% g, 500g C Citrate ACS, 99.5% (T) g C Chlorophyll a 85.0% (HPLC) mg, 5mg C Chlorogenic acid 95% g, 5g C Chlorogenic acid 98% g, 5g C Chondroitin 4-sulfate sodium salt 85% g, 100g, 500g C Chondroitin 4-sulfate sodium salt lyophilized powder,for cell culture, 85% g, 25g C Cynaroside 98.0% (HPLC) mg, 100mg C (±)-Citronellal 96% ml, 100ml, 500ml C Catalpol 97% (HPLC) mg C Natrualβ-Carotene 96% g, 5g, 25g C D-calcium pantothenate USP g, 100g, 500g C D-calcium pantothenate 98% g, 100g, 500g C Curcumin AR g C Curcumin 98% g, 5g, 25g, 100g C (±)-Camphor 96% g, 500g, 25kg C Cyelohexanecarboxylic acid 98%,Kosher kg, 5kg, 25kg C (S)-(+)-Camptothecin 97% mg, 500mg, 1g C Carvomenthenol 98% g, 100g C Chlorophyll b 95% mg C L(-)-Carvone 99% g, 100g, 500g C Cryptochlorogenic acid 98%(HPLC) mg, 1g C Candelilla wax g, 1kg D ,8-Dihydroxy-3-methylanthraquinone 97% mg, 250mg, 1g D Diosgenine 90% g, 25g, 100g D Diosgenine 95% g, 5g D Dihydrolinalool 95% ml, 100ml, 500ml D Dopamine hydrochloride 98% g, 25g, 100g D Decanal 97% ml, 500ml D Decanoic acid AR,99% ml D Decanoic acid CP,98% ml D Dihydrocapsaicin 90% mg, 100mg D Diheptyl phthalate 98+% g D ,7-Dihydroxycoumarin 98% g, 5g E (-)-Epigallocatechin 98%(HPLC) mg, 50mg, 250mg E Ethyl 3-hydroxybutyrate 98% g, 100g, 500g E Ethyl palmitate 98% g, 100ml, 500ml E Ergosterol 95% g, 25g, 100g E Ergosterol 97% g, 25g E Esculin hydrate 99% g, 25g, 100g E Ethyl 3-Phenylpropionate 98% g, 100g, 500g E Ethyl oleate 75%(GC) ml, 500ml, 2.5L E Ethyl oleate 98% ml, 25ml E Eugenol 99% g, 100g, 500g E Eucalyptol 99% ml, 500ml E Eucalyptol >99.5%(GC) ml E Erucic acid 80% g, 250g, 1kg, 5kg E Erucic acid 99%(GC) g, 5g E Ethylphenol 97% g, 100g, 500g, 1kg E Ethyl maltol 99% g, 100g E Epigoitrin 98% mg, 50mg 4

5 E Eriocitrin 98.0%(HPLC) mg F Ferulic acid 99% g, 50g, 250g, 1kg, 5kg F Folinic acid calcium salt hydrate 98% g, 5g F Fisetin 98% mg, 500mg, 5g F trans-ferulic Acid 99% g, 25g, 100g, 500g F FLAG Peptide Peptide 0.5mg, 1mg, 2.5mg G D(+)-Glucosamine hydrochloride 99% g, 100g, 500g G [10]-Gingerol 95% mg G Guanine 99% g, 100g, 500g G L-Glutamine 99% g, 100g, 500g G L-Glutathione reduced 98% g, 5g, 10g, 25g, 50g, 100g, 250g G L-Glutathione reduced For cell culture,98% g, 25g, 100g G L-Glutathione oxidized g, 5g, 25g G Gibberellic acid >90%(HPLC) g, 5g, 25g G Gibberellic acid 96%(HPLC) g, 5g, 25g G Gibberellic acid Analytical Standards mg G Gibberellic acid For plant cell culture, 96%(HPLC) g, 5g G Gum tragacanth powder USP grade g, 250g, 500g G Geraniol 98% ml, 100ml, 500ml G Gramine 98% g, 100g, 500g G alpha-Glycyrrhetinic acid 95% mg G Glycyrrhizic acid 93% g, 5g, 25g G Guaiacol >99.0%(GC) g, 500g, 5kg G Guaiacol CP,98.0% g, 500g G Genistin Analytical Standards, 98% mg G Ginkgolic Acids(C13:0,C15:1, C17:2,C15:0,C17:1) 90% 10mg G Geranyl Acetone 97% ml, 100ml G Glucosyl-vitexin 98% mg, 50mg H trans-2-hexen-1-ol 97% ml, 100ml, 500ml H (4S)-4-Hydroxy-L-isoleucine 95% mg, 50mg H Hesperidin 97% g, 100g, 500g H (-)-Huperzine A 98% mg H Hydroxytyrosol 98% mg, 500mg, 1g H Hesperitin 97% g, 5g, 25g H Hydroxyecdysone 93% (HPLC) powder mg, 100mg H Hydroxyecdysone 95% (HPLC) powder mg, 100mg H Hypericin 96% mg, 250mg H Honokiol 98% (HPLC) mg, 250mg, 1g I Isopropyl benzoate 99% ml, 100ml I Inosine 98% g, 100g, 500g I Indole-3-carbinol 96% g, 5g, 25g I Inositol 99% g, 100g, 500g I Isorhamnetin 90% mg I Isorhamnetin >98%(HPLC) mg, 1g I Isopropyl ether >99.0% (GC)(Containing 100 PPM BHT stabilizer) ml, 2.5L I Inulin from dahlia tubers BC g, 50g, 250g I Isoliquiritigenin 98% mg, 1g, 5g I Isophytol 95% ml, 100ml, 500ml I Isonaline % ml, 100ml, 500ml I Isobornyl propionate 95% Kg 5

6 J cis-jasmon 98% ml, 25ml, 1kg, 5kg L Linoleic acid 99.0% (GC) g, 5g, 25g, 100g, 500g, 1kg L Linoleic acid >95.0%(GC) g, 100g, 500ml L Linoleic acid >97.0%(GC) g, 25g, 100g L Linalyl Acetate 96% ml, 100ml, 500ml L Lycorine hydrochloride 96%(HPLC) g, 5g L Linolenic acid 99% mg, 1g, 5g L Linolenic acid ~70%(GC) ml, 25ml L Linolenic acid 97.0%(GC) ml, 5ml, 25ml L Linalool 98% ml, 100ml, 500ml L Luteolin 98%(HPLC) mg, 1g, 5g L Loganin 98% mg, 50mg L Locust bean gum from Ceratonia siliqua seeds g, 1kg, 5kg M Methylacrylic acid >99.0%(GC),250ppm MEHQ stabilized ml, 2.5L, 10L M Methylacrylic acid CP,98% ml M Mogroside V 98% g M Methyl cedryl ketone kg, 5kg M Malonate AR,99.5% g, 500g, 2.5kg M Malonate CP,98% g M Methyl isopropyl ketone 99% ml, 250ml, 1L M Methyl sulfide 99% ml, 1L M Methyl γ-linolenate 99% mg M DL-Menthol 99% ml, 100ml, 500ml M DL-Menthol Analytical Standards mg M L-(-)-Malic acid 98% g, 100g, 500g M L-(-)-Malic acid CP g, 100g M Methyl cinnamate 99% g, 500g M Mucic acid 98% g, 100g, 500g M Madecassoside 98% mg M Methyl myristate 98% kg, 25kg M Methyl myristate 98% ml, 500ml M Methyl behenate 85% g, 100g M Methylbutyric acid 98% ml, 100ml, 500ml M Maltol 99% g, 100g, 500g M Methyl Dihydrojasmonate 96% ml, 100ml M Myristic acid 98% g, 2.5kg M Myristic acid 98%,FCC, g, 1kg, 10kg, 25kg M Myristic acid 99%(GC) g, 500g M Methyl benzoate AR,98% ml M Methyl benzoate 99% ml, 5L M Maleic acid AR, 99.0%(HPLC) g, 100g, 500g, 5kg, 25kg M Maleic acid CP,99% g M Maleic acid USP,EP,USP g M Methylglyoxal 40% solution g, 1kg, 10kg M Methylglyoxal 32% solution g, 1L M Matrine 98% mg, 1g, 5g M Methyl salicylate AR,99% ml M Methyl salicylate CP,98% ml M Methyl salicylate USP,99% ml M Methyl oleate CP, 60.0%(GC) ml, 500ml, 25L, 20kg M Methyl oleate 99% g, 5g, 25g 6

7 M Methyl oleate 96% g, 25g M Magnolol 98%(HPLC) mg, 250mg M Myricitrin 98% mg M Melatonin 98% mg, 1g, 5g M Monensin decyl ester mg M Methyl behenate 99% g M L-(-)-Malic acid For cell and insect cell culture g, 100g, 500g N Nerolidol (cis and trans) Mixture of cis and trans ml, 100ml, 500ml N Nerol 97% ml, 100ml, 500ml N Nicotinic acid 99% g, 100g, 500g N Nicotinamide 99% g, 500g N Naringin 95% g, 50g N Nicotinamide 99.5%(HPLC) g, 500g N Nicotinamide For cell and insect cell culture, 99.5%(HPLC) g, 500g N Neochlorogenic acid 99% mg, 50mg N DL-Norephedrine hydrochloride 99+% g, 100g N FMP 100g N Neryl acetate 95% ml, 100ml N Nicotinic acid For cell and insect cell culture, 99% g, 500g N Nicotinic acid For plant cell culture, 99% g O Osthole 99% g, 5g O n-octanoic acid CP,98% ml O n-octanoic acid AR,99% ml, 2.5L, 10L O Orotic Acid Monohydrate 98% g, 100g, 500g O Oleic acid CP ml O Oleic acid AR ml O Oleic acid 99% ml, 5ml, 25ml O Oleic acid 85% ml, 500ml, 5L O Oleic acid USP ml O Oleanolic acid 97% mg, 500mg, 1g, 5g O Oridonin 98% mg O Ocimene 90% ml, 500ml P Phytin Ca: 20.0 ~ 24.0 % g, 250g P Palmitic acid AR g, 25kg P Palmitic acid 97% g, 2.5kg, 25kg P Palmitic acid 99% g, 25g, 100g P Paeoniflorin 98%(HPLC) mg, 500mg, 5g P Pyrogallic AR,98% g, 500g P Pyrogallic >99.0%(GC) g, 500g P Paclitaxel 98% mg, 50mg, 250mg P Pseudolaric Acid B 98% mg, 500mg P Phytic acid solution 50%solution g, 500g P Phytic acid solution For molecular biology,90% g, 25g, 100g, 500g P Phytic acid Analytical Standards mg P Phytic acid solution 70%solution g, 500g P L-Proline 99% g, 100g, 500g, 1kg P Polydatin 95% (HPLC) g, 5g, 25g P Protopine 98% mg, 100mg, 500mg P Propionic acid AR, 99.5% (GC) ml P Propionic acid CP, 99% (GC) ml P Propionic acid ACS reagent, 99.5% ml, 500ml P Propionic acid for insect cell culture, 99.5% L 7

8 P Picrolonic acid AR g, 5g P Palmitoleic acid 98.50% mg, 500mg P Puerarin 98% g, 5g P Palmatine 97% g, 25g P Pentagalloylglucose 96% mg, 25mg P Phloridzin dihydrate 98% g, 5g P Pentadecanoic Acid 98% g, 50g, 250g P Picroside II 98%(HPLC) mg, 50mg Q Quercetin 3-β-D-glucoside 90%(HPLC) mg, 50mg Q Quercetin 97% g, 50g R Riboflavine 98% g, 100g, 500g R Rutin hydrate 98% g, 25g, 100g, 500g R Rutaecarpine 98% mg, 1g R Rutin trihydrate 97% g, 100g, 500g R Rosmarinic acid 97% g, 5g R Rhein 98% mg, 50mg S Sodium alginate CP,viscosity: 200±20mpa.s g, 1kg S Sodium alginate BC g, 100g S Sodium alginate AR,90% g, 100g S Scopoletin 98% mg, 250mg S Sanguinarine chloride hydrate 98% (HPLC) mg S Syringic acid 98% g, 25g, 100g, 500g S Salicylic acid AR,99.5% g, 1kg S Salicylic acid CP,99.0% g S Salicylic acid ACS, 99.0% g, 1kg S Sodium salicylate AR,99.5% g, 1kg S Sodium salicylate CP,99.5% g S Sodium salicylate USP grade g, 1kg S Sinomenine 97% g, 5g S Sinapic acid 98% g, 5g, 25g S SAM p-toluenesulfonate salt 80% mg, 500mg S (-)-Scopolamine hydrobromide trihydrate 98% g, 5g, 25g S Stevioside hydrate 80% g, 100g S Stearic acid 40%, melting point: g S Stearic acid 98%,melting point:69-72 C g, 5kg, 25kg S Sodium stearate USP grade g, 250g, 500g, 1kg S Sodium stearate 96% g, 25g, 100g, 500g S Silibinin 98% g, 5g S Sodium Danshensu 98% mg, 1g S Stachydrine hydrochloride 98% g S DL-Sulforaphane 97.00% mg, 250mg, 1g S Sennoside C 99% mg, 100mg, 1g S Sinensetin 90% mg S Salicylic acid For plant cell culture, 99% g T Tryptamine 98% g, 25g T Ethylene brassylate 98% ml, 100ml T Tetrahydropalmatine 97% g T Taurine 99% g, 100g, 500g T Taurine USP grade g, 100g, 500g T Thymol AR,98% g, 100g, 500g T Thymol >99.0%(GC) g, 100g, 500g T DL-α-Tocopherol 96% g, 100g, 500g 8

9 T DL-Thioctic acid 99% g, 25g, 100g T Theobromine 99% g, 100g, 500g T (+)-δ-tocopherol 90% g T Polydatin 97% g, 5g T Tetrahydrogeraniol 98% ml, 100ml T Tryptamine hydrochloride 98+% g, 5g, 100g T Tanshinone I 97% mg, 500mg U Ursolic acid 93% mg, 1g U (+)-Usnic acid from Usnea dasypoga 98% g, 25g U γ-undecanolactone 98% ml, 100ml, 500ml U Undecanone 99% ml, 100ml, 500ml V Vindoline 98.0%(HPLC) mg V Vitamin B12 98% g, 5g, 25g V Vitamin B₁₂ For cell and insect cell culture mg, 1g V Vitamin K1 98% g, 5g, 25g V Vanillic acid 98% g, 100g, 500g V Vitamin E acetate 96%(HPLC) g, 25g, 100g, 500g V Vanillylacetone 98% g, 5g, 25g W Wilforlide A 98% mg, 250mg X Xylitol 99% g, 100g, 500g X D-(+)-Xylose 98% g, 500g X D-(+)-Xylose Analytical Standards, 99% mg X D-(+)-Xylose UP, 99% g, 100g, 500g X Xanthophyll 75% mg, 25mg 9