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Nuclear Receptors Product Listing | Edition 2

Kudzu Pueraria lobata A source of Daidzein

Nuclear Products by Group: • Receptor Group • Thyroid -like Group • X Receptor-like Group • Steroidogenic Factor-like Group Tocris Product Listing Series Contents This listing contains over 150 products from Tocris, including a wide range of agonists and antagonists available for each nuclear receptor group. Related products are also listed, alongside a selection of relevant scientific literature available from www.tocris.com.

Introduction...... 3 -like Group (continued)

Pregnane X Receptor (PXR)...... 9 Receptor Group...... 5

Retinoic Acid Receptors (RAR)...... 10 Receptor (AR)...... 5 Rev-Erb Receptors...... 11 Receptors (ER)...... 5 Thyroid Hormone Receptors (TR)...... 11

Estrogen-related Receptors (ERR)...... 7 Receptor (VDR)...... 11

...... Receptor (GR) 7 -like Group...... 12

Mineralocorticoid Receptor (MR)...... 7 Hepatocyte Nuclear Factor-4 (HNF-4) Receptors...... 12

Retinoid X Receptors (RXR)...... 12 Receptor (PR)...... 7

Steroidogenic Factor-like Group...... 13 Thyroid Hormone Receptor-like Group...... 8

Liver Receptor Homolog-1 (LRH-1)...... 13 Constitutive Androstane Receptor (CAR)...... 8 Steroidogenic Factor-1 (SF-1)...... 13

Farnesoid X Receptors (FXR)...... 8 Related Products...... 14

Liver X Receptors (LXR)...... 8 (CYP19)...... 14

Peroxisome Proliferator-activated Receptors (PPAR)...... 8 Aryl Hydrocarbon Receptor (AhR)...... 14

2 | NUCLEAR RECEPTORS Introduction Nuclear receptors, also referred to as nuclear hormone receptors, are a subset of ligand-activated factors that can bind to specific sites on DNA and recruit transcription machinery, influencing expression. The 48 known nuclear receptors have been broadly classified into six main groups according to their sequence, with an additional, non-DNA binding group of receptors – DAX-like receptors (group 0) – also described (Figure 1).

Figure 1 | Classification of Nuclear Receptors

Group 1: Group 2: Group 3: Group 4: Group 5: Group 6: Thyroid Hormone Retinoid X Steroid Hormone Nerve Growth Steroidogenic Germ Cell Nuclear Receptor-like Receptor-like Receptors Factor IB-like Factor-like Factor Receptors

Constitutive Nerve Growth COUP-TF-like Androgen Liver Receptor Androstane Factor IB Germ Cell Nuclear Receptors Receptor Homolog 1 Receptor Receptor Factor

Hepatocyte Farnesoid X Estrogen Neuron-derived Steroidogenic Nuclear Factor-4 Receptors Receptors Orphan Receptor 1 Factor 1 Receptors

Liver X Retinoid X Estrogen-related Nuclear Receptors Receptors Receptors Receptor-related 1

Glucocorticoid PPAR Tailless-like Receptors Receptor

Pregnane X Testicular Receptor Receptors Receptor

RAR-related Progesterone Orphan Receptors Receptor Miscellaneous group

Retinoic Acid Group 0: Receptors DAX-like Receptors

Rev-Erb Receptors

DAX1 Thyroid Hormone Receptor Receptors

SHP Receptor

www.tocris.com | 3 Tocris Product Listing Series Introduction – continued

All nuclear receptors comprise five major domains: an N-terminal regulatory domain, a DNA-binding domain, a hinge region, a ligand-binding domain and a C-terminal domain (Figure 2). Some of these domains, such as the DNA-binding domain, are highly conserved between nuclear receptors whereas others, for example the N-terminal regulatory domain, are more variable. In addition to the phylogenetic classification of nuclear receptors (as described by the Nuclear Receptor Nomenclature Committee), nuclear receptors can also be separated into distinct types according to their functional characteristics. The principal difference between the types is in the location of the unbound nuclear receptor; prior to ligand binding, some nuclear receptors are located in the in a complex with heat shock , whereas others exist in the nucleus where they bind to DNA in a complex with transcriptional corepressors. The involvement of nuclear receptors in almost every cellular process, coupled with their innate ability to bind ligands and influence transcription, has led to significant drug discovery programs targeted at these receptors. Indeed, synthetic ligands for nuclear receptors such as estrogen receptors, glucocorticoid receptors and peroxisome proliferator-activated receptors, are currently used in the treatment of cancer, inflammatory disorders and metabolic disorders respectively. Further research into the physiological functions of these receptors may identify additional therapeutic targets within the nuclear receptor family.

Figure 2 | Canonical Nuclear Receptor Structure

N-terminal Domain DNA-binding Domain Ligand-binding Domain C-terminal Domain Hinge Region

A/B C E F D

Key Functions Key Functions Key Functions • Highly variable structure • Activation function-1 (AF-1) • DNA binding • Activation function-2 (AF-2) • Function unknown • Ligand-independent • Dimerization • Ligand binding transactivation • Transactivation • Dimerization • Nuclear localization • Coregulator binding

For further information on nuclear receptor structure and function, please refer to Gronemeyer et al (2004) Nat Rev Drug Discov 3 950

Tocris has a unique collection of products for nuclear receptors, from established biochemical standards to novel and exclusive licensed compounds. The information listed within is correct at the time of printing. For the latest information, and to request free scientific literature, please visit www.tocris.com.

4 | NUCLEAR RECEPTORS Group Steroid and their receptors are involved in a vast range of biological processes, from development to cholesterol regulation. Certain members of this family, such as estrogen receptors and androgen receptors, are also important targets for cancer research due to their involvement in tumor cell proliferation.

Category Cat. No. Product Name Description Unit Size (AR) Agonists 3812 Cl-4AS-1 Steroidal androgen receptor agonist 10 mg 50 mg 2822 Endogenous androgen receptor agonist 50 mg Antagonists 3389 Non-steroidal androgen receptor antagonist 10 mg 50 mg 4094 Flutamide Non-steroidal androgen receptor antagonist 50 mg 1759 Nilutamide Androgen receptor antagonist. Orally active 100 mg 3923 PF 998425 Non-steroidal androgen receptor antagonist 10 mg Modulators 3813 TFM-4AS-1 Selective androgen (SARM) 10 mg 50 mg Other 4626 Andrographolide Inhibits NF-κB; blocks AR expression 50 mg 3293 Finasteride Type II 5α-reductase inhibitor; antiandrogen 50 mg 4396 Piperlongumine Induces apoptosis; depletes androgen receptors in prostate 10 mg cancer cells 50 mg Estrogen Receptors (ER) Agonists 1417 Daidzein ER agonist. Also induces cell cycle arrest 50 mg 1494 DPN Highly potent ERβ agonist 10 mg 50 mg 4276 ERB 041 Potent ERβ agonist 10 mg 50 mg 2823 α- Endogenous ER agonist 50 mg 2824 β-Estradiol Endogenous ER agonist 100 mg 3523 FERb 033 Potent and selective ERβ agonist 10 mg 50 mg 3819 Liquiritigenin Selective ERβ agonist 10 mg 1426 PPT Subtype-selective ERα agonist 10 mg 50 mg 1990 (R,R)-THC Potent subtype-selective ligand; ERα agonist/ERβ antagonist 10 mg 3366 WAY 200070 Selective ERβ agonist 10 mg 50 mg

Key products for Estrogen Receptors

CF3 H H OH OH CF3 O O F F Me Me F F N N CFC3F3 HS S OH CF3 O O FO Me F F F NO2 O2 CF3 S O OH OH H H O O F O2 N HO HO N OH H HO HO O O O N H HH H NN N N S S H HO HO HOO O NN NH HO H H O OH OH N N S ERB 041 N HHOO H ERB 041 HO O OH ERB 041 (4276) ICI 182,780 (1047) LiquiritigeninLiquiritigeninLiquiritigenin (3819) ERB 041 ICI 182,780ICI 182,780 (1047) (1047) HO Potent ERβ agonist ER antagonist LiquiritigeninSelective ERβ agonist GSK 4716 ICI 182,780 (1047) GSK 4716 GSK 4716 F F F CF3 CF3 GSK 9027 GSK 9027 O CF3 HO2C N O O GSK 9027 HO2C N O S N O O O CO2H N S NH O S CO H O N N O HO2C N O 2 O O Ph O NH S O O Ph S O CO H OEt N OS N O O N O O 2 N S O NH O S O OEt O O O N N H O Ph H O O O O O NH O H S H N Et OEt Cl O O HN NH N O N N Et O Tesaglitazar Cl H O O HN H O NH Pioglitazone Tesaglitazar N Et Cl O HN O Pioglitazone Tesaglitazar GSK 3787 (3961)www.tocris.com | 5 O O2N Pioglitazone GSK 3787 (3961) F3C O2N F3C GSK 3787 (3961) O2N F3C SR 1664 (4409) GW 6471 (4618) SR 1664 (4409) GW 6471 (4618) SR 1664 (4409) GW 6471 (4618) CO2H N CO2H CO Et 2 N CO2H NO CO2Et N 2 S S HO O CO2H N O N S NO CO2Et O N 2 S S HO O CO2H N O O NO N O S 2 S S HO GC 1 (4554)O CO2H N O S CO2H O MM 11253 (3822) O S GC 1 (4554) S CO2H SMe O MM 11253 (3822) S GC 1 (4554) CO H BI 6015 MM 11253 (3822) 2 SMe BI 6015 SR 8278SM (4463)e HO2C BMS 453 (3409) BI 6015 SR 8278 (4463) HO2C BMS 453 (3409) SR 8278 (4463) HO2C O OEt BMS 453 (3409) N O O N N N O OEt O N O O O N CN O OEt N N N HO N N N NO2 O O O N N O HN N CN N N N HO O NC CN NO O N N N CN 2 AC 45594 N CN N HO HN O NO N 2 NC CN N HX 531 NHON AC 45594 CN Letrozole Cl O Anastrazole NC CN Cl N AC 45594 CN HX 531 OSID 7969543O Cl Letrozole HX 531 Cl O Anastrazole N Letrozole Cl AnastrazoleS Cl OH SID 7969543 O H N HO N N OMe N N O SID 7969543 N H S N N OH H O N H O N N HO O N N S OMe N O OH O H N N N HO HHO N N N H N Me N O N Cl Me H OMe N O N N H N O H S N N Cl N N H N O HO H N O N ITE (1803) N CH 223191 (3858) N Cl Me Me H Liarazole N CITCO HO CalcipotriolH N Cl N S N Cl Me Me H ITE (1803) Cl S N CH 223191 (3858) Liarazole CITCO Calcipotriol ITE (1803) CH 223191 (3858) Liarazole CITCO Calcipotriol Tocris Product Listing Series

Category Cat. No. Product Name Description Unit Size Antagonists 0743 DPPE Antiestrogen; displays antiproliferative activity in vitro 10 mg 50 mg 3705 Endoxifen Potent antiestrogen; ERα ligand 10 mg 50 mg 1047 ICI 182,780 ER antagonist 1 mg 10 mg 50 mg 1991 MPP Highly selective ERα antagonist 10 mg 50 mg 2662 PHTPP Selective ERβ antagonist 10 mg 50 mg 3224 RU 58668 Pure antiestrogen 10 mg 0999 Tamoxifen Antiestrogen; ER partial agonist/antagonist 100 mg 1990 (R,R)-THC Potent subtype-selective ligand; ERα agonist/ERβ antagonist 10 mg 2183 ZK 164015 Potent ER antagonist 10 mg 50 mg Ligands 1110 Genistein ER ligand. Also tyrosine kinase inhibitor 10 mg 50 mg 3975 Zearalenone ER ligand; mycotoxin 10 mg 50 mg Modulators 3999 Cyclofenil Selective ER modulator 10 mg 50 mg 2280 Raloxifene Selective ER modulator 50 mg 2676 Y 134 Selective ERα modulator 10 mg 50 mg

Selective ERRβ and ERRγ Agonist Agonist GSK 4716 Cat. No. 3075 GSK 9027 Cat. No. 4116

H OH CF3 O N CF F Me F 3 H S OH CF3 O N CF O F O2 F Me F 3 H O S OH O F O2 H O HO N HO O OH N H H N N S N HO O N HO N H H H HO O OH N N S N H ERB 041 HO HO O OH Liquiritigenin HO ICI 182,780 (1047) ERB 041 Liquiritigenin GSK 4716 is ICIa selective 182,780 (1047) GSKagonist 4716 at estrogen-related receptors GSK 4716 F ERRβ and ERRγ. The compound displays selectivity for ERRβ and ERRγ over ERRα and the classical estrogen receptors. F CF3 GSK 9027 CF3 O GSK 9027 HO2C GSK 9027 is a glucocorticoid receptor agonist (pIC50 = 8). The N O O HO C S N O compound inhibits production of the proinflammatory mediator 2 O CO2H N N O NH S O IL-6 . O Ph S N in vivo O O O O CO2H N O S NH S O OEt O N O Ph O O N O O (Sold for research purposes under agreement from GlaxoSmithKline) O H O OEt S N H NH N O O N Et O H O Cl O HN H NH Tesaglitazar N Et O Cl O HN Pioglitazone Tesaglitazar O Pioglitazone GSK 3787 (3961) O N F C 2 3 GSK 3787 (3961) O2N F3C

SR 1664 (4409) GW 6471 (4618) SR 1664 (4409) GW 6471 (4618)

CO2H CO2H N CO2Et N NO CO Et HO O CO H N 2 2 S S 2 N6 | O S N NO2 S S HO O O CO2H N O O O S GC 1 (4554) S O CO2H MM 11253 (3822) GC 1 (4554) S CO2H MM 11253 (3822) SMe BI 6015 SMe BI 6015 SR 8278 (4463) HO2C BMS 453 (3409) SR 8278 (4463) HO2C BMS 453 (3409)

O OEt N O O N O OEt N N O O N O N N CN O N N O N HO N O N CN NO2 N N HN HO N NO2 N NC CN N HN AC 45594 CN NC CN O N AC 45594 CN HX 531 O O Letrozole Cl HX 531 Anastrazole O Cl Letrozole Cl Anastrazole SID 7969543 Cl SID 7969543 N S OH N O H N HO N S N O OMe ONH O H N N HO N H N O OMe N N N H N O N H O N N N O N H O N HO H N N N Cl Me Me H N HO H N N Me H Cl S N Cl Me Cl ITE (1803) S N CH 223191 (3858) Liarazole CITCO Calcipotriol ITE (1803) CH 223191 (3858) Liarazole CITCO Calcipotriol NUCLEAR RECEPTORS Steroid Hormone Receptor Group – continued

Category Cat. No. Product Name Description Unit Size Estrogen-related Receptors (ERR) Agonists 2266 DY131 Selective ERRβ and ERRγ agonist 10 mg 50 mg 3075 GSK 4716 Selective ERRβ and ERRγ agonist 10 mg 50 mg Antagonists 3928 XCT 790 Selective ERRα antagonist/inverse agonist 10 mg 50 mg Glucocorticoid Receptor (GR) Agonists 2671 Budesonide Synthetic glucocorticoid; anti-inflammatory and 50 mg chemopreventive agent 3685 Endogenous glucocorticoid 50 mg 1126 Dexamethasone Anti-inflammatory glucocorticoid 100 mg 2007 Fluticasone Selective, high affinity glucocorticoid agonist 10 mg 50 mg 4116 GSK 9027 Glucocorticoid receptor agonist 10 mg 50 mg 4093 Hydrocortisone Adrenal glucocorticoid; immunosuppressant 50 mg 4115 Mometasone Synthetic corticosteroid; anti-inflammatory agent 50 mg Antagonists 1479 Glucocorticoid and antagonist 100 mg Mineralocorticoid Receptor (MR) Agonists 3685 Corticosterone Endogenous glucocorticoid and mineralocorticoid 50 mg receptor agonist Antagonists 3934 Benidipine Mineralocorticoid receptor antagonist. Also blocks Ca2+ 10 mg channels 50 mg 3281 Canrenone Mineralocorticoid receptor antagonist 50 mg 2397 Eplerenone Selective mineralocorticoid receptor antagonist 10 mg 50 mg 2970 RU 26752 Mineralocorticoid receptor antagonist 10 mg 1672 RU 28313 Potent, selective mineralocorticoid receptor antagonist 10 mg 50 mg 2968 Spironolactone Mineralocorticoid receptor antagonist 50 mg Progesterone Receptor (PR) Agonists 4833 Levonorgestrel Synthetic progesterone analog 50 mg 4115 Mometasone Synthetic corticosteroid; progesterone receptor agonist 50 mg 2835 Progesterone Endogenous progesterone receptor agonist 100 mg Antagonists 1479 Mifepristone Progesterone and glucocorticoid receptor antagonist 100 mg

www.tocris.com | 7 Tocris Product Listing Series Thyroid Hormone Receptor-like Group Members of the thyroid hormone receptor-like group are involved in a wide range of cellular processes, including embryogenesis and cellular differentiation (retinoic acid receptors), bone homeostasis (vitamin D receptors) and the detection and clearance of foreign toxic substances (pregnane X receptors).

Category Cat. No. Product Name Description Unit Size Constitutive Androstane Receptor (CAR) Agonists 3683 CITCO Selective CAR agonist 10 mg 50 mg 1225 TCPOBOP CAR agonist 10 mg 50 mg Farnesoid X Receptors (FXR) Agonists 2563 Fexaramine Potent, selective agonist 10 mg 50 mg 2473 GW 4064 Selective farnesoid X receptor agonist 10 mg 50 mg Liver X Receptors (LXR) Agonists 2474 GW 3965 Orally active agonist 1 mg 10 mg 2373 T 0901317 Potent liver X receptor agonist 10 mg 50 mg Peroxisome Proliferator-activated Receptors (PPAR) Agonists 1307 Ciglitazone Selective PPARγ agonist 10 mg 50 mg 4190 CP 775146 Selective, high affinity PPARα agonist 10 mg 50 mg 4113 Fenofibrate PPARα agonist 50 mg 2229 GW 0742 Highly selective, potent PPARδ agonist 10 mg 50 mg 1664 GW 1929 Selective PPARγ agonist; orally active 10 mg 50 mg 1677 GW 7647 Highly selective, potent PPARα agonist; orally active 10 mg 50 mg 1856 L-165,041 Potent PPARδ agonist 10 mg 50 mg 3831 LG 100754 RXR:PPAR agonist; sensitizes PPARγ 10 mg 50 mg 2150 nTZDpa Potent, selective PPARγ partial agonist 10 mg 50 mg 1484 Oleylethanolamide PPARα agonist. Also GPR55 agonist 10 mg 50 mg 0879 Palmitoylethanolamide Endogenous with PPARα agonist activity 10 mg 50 mg 4124 Pioglitazone Selective PPARγ agonist; antidiabetic agent 10 mg 50 mg 12,14 2306 15-deoxy-∆- -Prostaglandin J2 Endogenous PPARγ agonist 1 mg 3690 S26948 Selective PPARγ agonist; antidiabetic agent 10 mg 50 mg 3965 Tesaglitazar PPARα/γ agonist 10 mg 50 mg 3114 Troglitazone Selective PPARγ agonist; antidiabetic agent 10 mg 50 mg 1312 WY 14643 Selective PPARα agonist 10 mg 50 mg

8 | NUCLEAR RECEPTORS Thyroid Hormone Receptor-like Group – continued

Category Cat. No. Product Name Description Unit Size

Antagonists 1326 BADGE PPARγ antagonist 10 mg 50 mg 4344 FH 535 PPARγ/δ antagonist. Also inhibits Wnt/β-catenin signaling 10 mg 50 mg 3433 GSK 0660 Selective PPARδ antagonist 10 mg 50 mg 3961 GSK 3787 Potent and selective PPARδ antagonist 10 mg 50 mg 4618 GW 6471 PPARα antagonist 10 mg 50 mg 1508 GW 9662 Selective PPARγ antagonist 10 mg 50 mg 1311 MK 886 PPARα antagonist. Also inhibits FLAP 10 mg 50 mg 2022 SR 202 Selective PPARγ antagonist; antidiabetic and antiobesity agent 10 mg 50 mg 2301 T 0070907 Highly potent and selective PPARγ antagonist 10 mg 50 mg Ligands 1110 Genistein PPARγ ligand. Also ligand and EGFR 10 mg inhibitor H OH CF3 O 50 mg F Me F HN CF3 4409 SR 1664 High affinity PPAROH γ ligand; blocksC FCdk5-dependent3 PPARγ phosphorylationO 10 mg S HN CF O F Me OH F CF3 O O 3 F Me F F S 2N CF3 H 50 mg O O OH F SO2 O F O OH H 2 O Pregnane X ReceptorHO (PXR) N H HO O O N OH H H N HO N HO O N N Agonists 4245 NMeclizine PregnaneH HX receptor agonist. Also H1 antagonistS 50 mg H HO HO O HO O N N N N H H S OH N NH 4121 Rifampicin agonist; antibioticS 50 mg N ERB 041 HO O OH N HO H HO O OH 2969 ERB 041SR 12813 Pregnane X receptor agonist Liquiritigenin 10 mg HO ICI 182,780 (1047) HO ERB 041 Liquiritigenin 50 mg ICI 182,780 (1047) Liquiritigenin GSK 4716 ICI 182,780 (1047) GSK 4716 F GSK 4716 H OH CF3 O F F Me F Key Products for PPAR N CF3 S H F OH CF3 O CF3 O F Me F O N CF3 F 2 CF GSK 9027 H S O 3 O OH OO CF3 GSK 9027 F 2 GSK 9027 HO2C H N O O HO N OH HO O O N HO2C H H S O N N O O N CO2H N N O HO2C HO N S HO O N O S NH S N H N O N HO H H O O CO2H O Ph N O OH S O N N O N O O S NH S OO CO2H H S Ph N HO O NH S N HO OEt O O O O N ERB 041 OH O O O N S O Ph O O OEt H O O O N Liquiritigenin O HO N S H NH ERB 041 ICI 182,780 (1047) O O OEt O O N Et N NH H Liquiritigenin O O Cl H O O HN NH ICI 182,780 (1047) GSK 4716 HN Et NH Tesaglitazar Cl O HN N Et Pioglitazone (4124) TesaglitazarTesaglitazar (3965) GSKCl 4716 GSK 3787 (3961) O HN O Pioglitazone F Tesaglitazar O Pioglitazone O Selective PPARγ agonist; antidiabetic agent PPARα/γ agonist Potent and selectiveGSK 3787 PPAR(3961)δ antagonist Pioglitazone F O2N F3C CF3 GSK 3787 (3961) O N GSK 9027 GSK 3787 (3961) 2 F3C O2N CF3 F3C O GSK 9027 HO2C N O SR 1664 (4409) O HO C GW 6471 (4618) S O CO H N N O 2 SR 1664 (4409) N O 2 O GW 6471 (4618) SR 1664 (4409) NH S Ph S O CO H ON N O O GW 6471 (4618) O O 2 O S NH S OEt OPh N N O CO2H O O O O O H O S OEt O CO H H NH N N 2 N Et N O O H O CO2H Cl O HN H NH CO2Et N Tesaglitazar N Et CO Et N Cl O HN 2 N NO2 O HO O CO H CO2Et Pioglitazone Tesaglitazar S S 2 N O NO N S 2 S S OHO O CO2H N O ON NO2 Pioglitazone GSK 3787 (3961) S S HO O CO2H O2N N O S F C O S O GSK 3787 (3961) 3 O GCO 12 N(4554) S O F3C CO2H O MM 11253 (3822) GC 1 (4554) S GW 6471 (4618) SR 1664 (4409) CO2H S MM 11253 (3822) GC 1 (4554) SR 1664 (4409) CO H MM 11253 (3822)PPARGWα antagonist 6471 (4618) High affinity PPARγ ligand 2 SMe SR 1664 (4409) SMe BI 6015 GW 6471 (4618) SMe BI 6015 BI 6015 CO2H SR 8278 (4463) HO2C BMS 453 (3409) N SR 8278 (4463) CO2H HO2C BMS 453 (3409) SR 8278 (4463) HO C CO Et 2 2 N BMS 453 (3409) CO Et NO HO O CO H 2 N 2 S S 2 N O O OEt N S N NO2 S S HO O CO2H O O O OEt O N N O N N SO OEt O N O O O O N N O O N GC 1 (4554) N S O O www.tocris.com | 9 N CN N CO2H O N N MM 11253 (3822) N HO S O O N CN GC 1 (4554) NO N NN CN 2 CO2H HO O N MM 11253 (3822) N NO SMe HN N 2 HO N N NO2 SMe BI 6015 HN NC CN N N HN AC 45594 CN NC CN BI 6015 N O AC 45594 CN NC CN SR 8278 (4463) N O CN HO2C BMS 453HX (3409) 531 AC 45594 O O SRC 8278l (4463) Letrozole HO2C HXBMS 531 453 (3409) O Anastrazole HX 531 Cl Cl O Letrozole Anastrazole Letrozole Cl Cl SID 7969543 Anastrazole Cl N O OEt SID 7969543 ON SID 7969543 O O OEt N N S N O N O H N O N O OH N S N N CN HO O S N O N N O OHN OMe H NN N O OH HO O N HN N HO O N H N N O CN HO OMe N N NO2 N N N N OMe N N O H N O N HO HN H N N O N NO2 HN N H N O N N N NC CN O N O N HN N HO H H N O N AC 45594 N CN Me H N O N Cl NC HO CN MHe N N N HO H Me NH AC 45594 S N N CN Cl Me HX 531 O Cl O N Cl Me Me H Cl Cl S N Letrozole ITE (1803) HX 531 Cl O AnastrazoleS N CH 223191 (3858) Cl Letrozole ITE (1803) Cl Liarazole AnastrazoleCITCO Calcipotriol CH 223191 (3858) Cl SID 7969543 ITE (1803) CH 223191 (3858) Liarazole CITCO Calcipotriol Liarazole CITCO Calcipotriol N SID 7969543 S N OH O H N HO S N N O OH O OMe H N N HO N N N H OMe N N N O H N N O H O N N N H N O N HO H N O N N Cl Me Me H N HO H N N Me H Cl S N Cl Me Cl S N ITE (1803) CH 223191 (3858) Liarazole CITCO Calcipotriol ITE (1803) CH 223191 (3858) Liarazole CITCO Calcipotriol Tocris Product Listing Series

Category Cat. No. Product Name Description Unit Size Retinoic Acid Receptors (RAR) Agonists 4046 AC 261066 RARβ2 agonist 10 mg 50 mg 2436 AC 55649 Selective RARβ2 agonist 10 mg 50 mg 2852 RARβ and RARγ agonist 10 mg 50 mg 0760 AM 580 Retinoic acid analog; RARα agonist 10 mg 50 mg 3507 AM 80 RARα agonist; anticancer 10 mg 50 mg 3409 BMS 453 Synthetic retinoid. RARβ agonist; also RARα and RARγ 10 mg antagonist 3505 BMS 753 RARα-selective agonist 10 mg 50 mg 3410 BMS 961 Selective RARγ agonist 10 mg 50 mg 2554 CD 1530 Potent and selective RARγ agonist 10 mg 50 mg 1549 CD 437 RARγ-selective agonist 10 mg 50 mg 2020 Ch 55 Potent RAR agonist 10 mg 50 mg 0695 Retinoic acid Endogenous agonist 50 mg 0761 TTNPB Retinoic acid analog; RAR agonist 10 mg 50 mg Antagonists 3660 BMS 195614 Selective RARα antagonist 10 mg 50 mg 3409 BMS 453 Synthetic retinoid. RARβ agonist; also RARα and RARγ 10 mg antagonist 3509 BMS 493 Pan-RAR inverse agonist 10 mg 50 mg 3800 CD 2665 Selective RARβ/γ antagonist 10 mg 50 mg 3823 ER 50891 Selective RARα antagonist 10 mg 50 mg 2021 LE 135 Selective RARβ antagonist 10 mg 50 mg 3822 MM 11253 RARγ-selective antagonist 10 mg 50 mg Other 4011 EC 23 Synthetic retinoid; induces differentiation of stem cells 10 mg 50 mg 1396 Synthetic retinoid; potent anticancer agent 10 mg 50 mg 3997 Receptor-selective retinoid; binds RARβ and RARγ 10 mg 50 mg

10 | H OH CF3 O F Me F N CF3 S O F O2 OH H O HO N HO O N H H N N S N H HO O OH ERB 041 HO Liquiritigenin ICI 182,780 (1047) GSK 4716

F

CF3 GSK 9027

O HO2C N O NUCLEAR RECEPTORS S N O CO2H N O NH S O Thyroid Hormone Receptor-like Group – continued O Ph O O O OEt S N N O O O H O H H NH OH CF3 O N Et F Me F N CF3 Cl O HN S Tesaglitazar O Category Cat. No. F Product Name Description O2 Unit Size O OH H Pioglitazone O GSK 3787 (3961) HO N Rev-Erb Receptors HO O N O2N H H N N F3C Agonists 3663 GSKS 4112 Selective Rev-Erbα agonist N 10 mg H HO O OH 50 mg ERB 041 HO SR 1664 (4409) H GW 6471 (4618) Antagonists 4463 SR 8278 LiquiritigeninRev-Erbα antagonist OH CF3 O 10 mg ICI 182,780 (1047) F Me F N CF3 50 mg S O F GSK 4716 O2 Thyroid Hormone Receptors (TR) H O OH CO2H CF3 O H F OH Agonists 4554 HOGC 1 N N High affinityCF TRα and TRβ agonist; thyromimetic HO O 10 mg N N F Me F 3 H H N S 50 mg N CO2Et H S N H O OH CF3 F O O2 CHFO3 O F Me F N CF3 GSK 9027 OH N NO2 H Vitamin D Receptor (VDR) S S O HO O CO2H OH ERB S041 HO N O O O O HO2C S F Agonists 2551 2 Active metabolite of vitamin D3; VDR agonist Liquiritigenin50 µg O HO N H N O HO O O N OH H H ICI 182,780 (1047) O S O 3206 DoxercalciferolCO H NVitamin D analog; VDRN agonistN O N 1 mg S 2 O 2 H GSK 4716 S HO N NH HO S O Ph N N GC 1 (4554) HO H H O 3993 EBOH 1089 VDR agonistO 1 mg O CO2H O O N MM 11253 (3822) N S OEt S N ERB 041 N N O HOH F HO OO O 3970OH Ercalcitriol ActiveO metabolite of vitamin D2; VDR agonist 1 mg SMe Liquiritigenin H H HO NH ERB 041 ICI 182,780 (1047) Other 4159 Alfacalcidol Prodrug of vitamin D3 (Cat. No. 4156) N Et 1 mg BI 6015 Cl CF3 Liquiritigenin O HN GSK 9027 ICI 182,780 (1047) Tesaglitazar4036 Calcifediol Prohormone of calcitriol (Cat. No. 2551). Major circulatingGSK 4716 1 mg O O HO SRC 8278 (4463) Pioglitazone form of vitamin DHO2C GSK 4716 BMS 453 (3409) 2 N O F 2700 Calcipotriol S Vitamin D analog 10 mgN O GSK 3787 (3961) 3O CO2H O N N NH F S F C 2O 3 50 mg O Ph O CF3 O O S GSK 9027 OEt O O OEt N N 4146 Ercalcidiol Metabolite of vitamin D2 O N 1 mg CF3 O H O O O GSK 9027 HOOC SR 1664 (4409) H NH N 4160 22-Oxacalcitriol Non-calcemic vitamin D3 (Cat. No. 4156)GW 6471 analog (4618) 2 1 mg N Et N O N Cl O HN O N O HO2C S O CO H 4157N Tacalcitol N O Synthetic vitamin D3 (Cat.Tesaglitazar No. 4156) analog 1 mg O N CN N O 2 O O N S NH S N HO O CO H 4156 O VitaminN PioglitazoneDPh3 O Precursor of calcifediol (Cat. No. 4036). Naturally 50 mg N O 2 CO H O NO2 O NH S O 2 SPh occurring form of vitaminN D HN OEt O O O N GSK 3787 (3961) H O N O O O S N OH CF3 O N 2 O OEt H O O F Me N F F3C N CF3 NC CN N H NH CO2Et N O O O AC 45594 S CN H O H N Et O O Cl O HN NH F N NO2 2 S S HO O CO2H N Et H O Tesaglitazar Cl Key Products for Thyroid Hormone Receptor-likeO HN Group OH HX 531 N O O SR 1664 (4409) Tesaglitazar O O S GW 6471 (4618) Letrozole Pioglitazone HO N Cl HO O Anastrazole N O H H Cl O N N Pioglitazone S H GSK 3787GC 1(3961) (4554) HO OS SID 7969543 N O2NCO H OH GSK 3787 (3961) F C CO H 2 MM 11253 (3822) 3 2 O2N HO F3C ERB 041 N SMe Liquiritigenin N S ICI 182,780 (1047) OH CO2Et O H N BI 6015 HO N N SR 1664O (4409) N ONOMGSK2e 4716 N S S GW 6471 (4618) HO SR 1664 (4409)O CO H N GW 6471 (4618) H 2 N O N S HO C N SR 8278 (4463) H F O N O 2 BMS 453 (3409) O N O N HO H S N CO2H MM 11253 (3822) GCN 1 (4554) CF3 Me CO2H Cl CO2H Me GSK 9027 H RARMMγ -selective11253 (3822) antagonist N O OEt O N S N N Cl CO2Et SMe HO2C O N O OCO2Et N ITEBI (1803) 6015 CH 223191 (3858) S N NO2 N O HO O CO H O N NO2 CO2H N N S S S S HO N O CO H 2 NHLiarazoleO SN O CITCO (3683)CITCO O Calcipotriol 2 N O N CN O Ph O O N S O O O S SelectiveO CAR agonist S SR 8278 (4463) HO HO2C OEt BMS 453 (3409) O N NO N N 2 O O O O H O N HN H NH GC 1 (4554)GC 1 (4554) S S N Et CO H CO2H Cl NC CN O HN MM 11253MM (3822) 11253 (3822) 2 N AC 45594 Tesaglitazar CN O O OEt O N SMe Pioglitazone SMe O O HX 531 O N BI 6015 BI 6015 GSKLetrozole 3787 (3961) N Cl N Anastrazole O O2N Cl BMS 453 (3409) SR 8278 (4463) N F3C CN O N RARβ agonist; RARα and RARγ antagonist SID 7969543 SR 8278HO (4463)Rev-ErbSRα 8278 antagonist (4463) N HO2C HO2C BMS 453 (3409)BMS 453 (3409) NO2 N HN N SR 1664 (4409) S GW 6471 (4618) NC CN OH O N H N CN HO AC 45594 O N N O OEt O N N OMe N O OEt HX 531 N O H O O CO2H O O N N Cl N N N O Letrozole H O Anastrazole N N O Cl N N N N O N CN CO2Et N O O HO N N H CN N SID 7969543 N N Me H N NO2 HO Cl N S MeS HO O CO H NO2 HO N N 2 N O N NO2 S N Cl S N HN S O HN OH O H N NC ITE (1803) CN HCHO 223191 (3858) N O N N Calcipotriol (2700) NC GC 1 (4554) CN OMe AC 45594 N CN O S N Liarazole CITCO O Calcipotriol CN GC 1 (4554) N CO H AC 45594 O HVitamin D3 analog High affinity TRα and TRβ agonist; thyromimetic 2 N MM 11253 (3822) N H N O HX 531 O O N HX 531 Cl O Letrozole SMe Anastrazole HOLetrozole H N Cl Cl AnastrazoleN BI 6015 Cl N Cl Me Me H SID 7969543 SID 7969543 Cl S N SR 8278 (4463) N HO2C BMS 453 (3409) S ITE (1803) CH 223191 (3858) N O H OH Liarazole S CITCO N Calcipotriol | HO O N www.tocris.comH 11 N O OH OMe N N HO N N N N H O OMe ON OEt N N N O O N H H O O N N N N O N H N O O N HO H N N N CN N O N N Cl HO Me Me H N H N HO N N Me H NO2 Cl S N Cl Me N HN S N ITE (1803) NC CN Cl CH 223191 (3858) N AC 45594 CN Liarazole CITCO Calcipotriol ITE (1803) CH 223191 (3858) O Liarazole CITCO Calcipotriol HX 531 O Cl Letrozole Cl Anastrazole SID 7969543

N S OH O H N HO N N OMe N O N H N N H N O O N N HO H N N Cl Me Me H Cl S N ITE (1803) CH 223191 (3858) Liarazole CITCO Calcipotriol Tocris Product Listing Series

H OH CF3 O Retinoid X Receptor-like Group F Me F N CF3 S O F O2 This group of nuclear receptors is involved in diverse biological processes, including development, OHmetabolism and H O stem cell differentiation. Members of this family have also been linked to diseases:HO retinoidN X receptor agonists exhibit HO O N H H N N S H anticancer activity, whilst mutations in hepatocyte nuclear factor-4 have been associated with type II diabetes mellitus.HO O N H OH OH CF3 O HO F Me F N CF3 ERB 041 S Liquiritigenin ICI 182,780 (1047) O F O2 Category Cat. No. Product Name Description Unit Size H O GSK 4716 OH Hepatocyte Nuclear Factor-4 (HNF-4) Receptors N N HO HO O 4641 BI 6015 Hepatocyte nuclear factor-4 receptor antagonist 10 mg F H H N Antagonists N α S N H 50 mg HO O OH CF3 Retinoid X Receptors (RXR) GSK 9027 ERB 041 HO O Agonists 3302 CD 3254 Potent and selective RXRα agonist 10 mg HO2C Liquiritigenin N O ICI 182,780 (1047) S N 50 mg O CO2H N O GSK 4716 NH S O 3687 RXR agonist 100 mg O Ph O O O OEt S N 4064 Fluorobexarotene RXR agonist 10 mg N O F O O H O H NH 3831 LG 100754 RXR:PPAR agonist 10 mg N Et Cl O HN CF3 50 mg Tesaglitazar GSK 9027 O 3411 SR 11237 Pan RXR agonist Pioglitazone 10 mg O HO C 2 50mg GSK 3787 (3961) N O O2N S N F3C O CO2H N O Antagonists 3912 HX 531 RXR antagonist 10 mg NH S O O Ph O 50 mg O O OEt S N SR 1664 (4409) N O 3303 UVI 3003 RXR antagonist 10 mg GW 6471 (4618) O O H O H NH 50 mg N Et Cl O HN Modulators 3508 LG 101506 Selective RXR modulator 10 mg Tesaglitazar CO2H O 50 mg N Pioglitazone Other 3913 HX 630 RXR synergist 10 mg CO2Et GSK 3787 (3961) N NO2 O2N S S 50 mg HO O CO2H F3C N O O S O S Hepatocyte Nuclear Factor-4SR 1664 α(4409) Receptor Antagonist Retinoid X Receptor Antagonist GC 1 (4554) CO H GW 6471 (4618) MM 11253 (3822) 2 BI 6015 Cat. No. 4641 HX 531 Cat. No. 3912 SMe BI 6015 CO2H SR 8278 (4463) N HO2C BMS 453 (3409) CO2Et

N NO2 S S HO O CO2H N O O OEt N O S O O N O N O N GC 1 (4554) S O N CN CO2H N MM 11253 (3822) HO N NO2 N BI 6015SMe is a hepatocyte nuclear factor-4α (HNF-4α) antagonist HN NC CN that represses expression of knownBI 6015 HNF-4 target . The N AC 45594 CN compound decreases HNF-4α-DNA binding and exhibits O HX 531 SR 8278 (4463)cytotoxicity in a range of human tumor cell lines, including human HX 531 is a potent RXR antagonist (IC50 = 18 nM). The O HO2C BMS 453 (3409) Cl Letrozole hepatocellular carcinoma. compound suppresses docosahexaenoic acid-induced adipose Cl Anastrazole differentiation-related (ADRP) expression in BeWo cells. SID 7969543

N (Sold under license) O OEt N S O OH O H N O N HO N N O OMe N N O N N N CN H O N N N H N O O N HO N NO2 HO N N H N HN N Cl Me Me H NC CN N Cl S N AC 45594 CN O ITE (1803) CH 223191 (3858) HX 531 O Liarazole CITCO Calcipotriol Cl Letrozole Cl Anastrazole SID 7969543

N S OH O H N HO N N OMe N O N H 12 | N N H N O O N N HO H N N Cl Me Me H Cl S N ITE (1803) CH 223191 (3858) Liarazole CITCO Calcipotriol H OH CF3 O N CF F Me F 3 H OH CF3 O S F Me F N CF3 O F O2 S H O OH O F O2 H O HO N OH HO O N H H N N N S HO O N HO H H N H HO O OH N N S N H ERB 041 HO O OH HO Liquiritigenin HO ERB 041 ICI 182,780 (1047) Liquiritigenin ICI 182,780 (1047) GSK 4716 GSK 4716 F F

CF3 GSK 9027 CF3 GSK 9027 O HO2C N O O HO2C S O CO H N N O N O 2 O NUCLEAR RECEPTORS NH S S Ph N O CO2H O N O O O O NH S S O OEt O O Ph N O O O O N O OHEt O S N N O H NH O O H O N Et Cl O HN H NH SteroidogenicTesaglitazar Factor-like Group N Et Cl O O HN Pioglitazone Tesaglitazar O SteroidogenicPioglitazone factor-like receptors regulate the differentiationGSK 3787 and (3961) function of endocrine glands. They are classed O2N F3C as ‘orphan receptors’ because no endogenous ligands for these receptors have beenGSK 3787identified. (3961) Details of their O N F C 2 transcriptional activity and how these receptors are regulated also remain unclear. 3 SR 1664 (4409) GW 6471 (4618) SR 1664 (4409) GW 6471 (4618) Category Cat. No. Product Name Description Unit Size Liver CReceptorO2H Homolog-1 (LRH-1) CO2H N Agonists 4378 DLPC Selective LRH-1 agonist 50 mg CO2Et N Steroidogenic Factor-1 (SF-1) N CO2Et NO2 S S HO O CO2H N O NO Antagonists 3043 AC 45594 SF-1 inverse agonist 10 mg S N 2 S S HO O CO2H ON O 50 mg O O S 3440 SID 7969543GC 1 (4554) Selective steroidogenic factor-1 (SF-1, NR5A1) antagonist 10 mg S O CO2H MM 11253 (3822) GC 1 (4554) S 50 mg CO2H MM 11253 (3822) SMe BI 6015SMe Steroidogenic Factor-1 Inverse Agonist Selective Steroidogenic Factor-1 Antagonist BI 6015 SR 8278 (4463) HO2C BMS 453 (3409) SR 8278 (4463) ACH 45594O2C Cat. No. 3043 SID 7969543 BMS 453 Cat.(3409) No. 3440

O OEt N O OO OEt N N O N O O N N N CN N O N O N HO O N N CN NO2 N N HO HN N NO2 N HN NC CN AC 45594 is a selective inverse agonist at the orphan nuclear N CN AC 45594 O NC CN receptor steroidogenic factor-1 (SF-1) (IC = 50 - 100 nM). The N CN 50 AC 45594 O HX 531 compound displays no activity at estrogen, LRH-1, ROR, ERR or O Letrozole HX 531 Cl O Anastrazole Nurr receptors. AC 45594Cl inhibits SFRE-mediated transcription. Letrozole Cl Anastrazole Cl SID 7969543 SID 7969543 N SID 7969543 is a selective steroidogenic factor-1 (SF-1, NR5A1) antagonist (IC values are 0.76, >33 and >33 µM atS SF-1, RORα N OH 50 O H N and VP16 receptorsHO respectively). The compound inhibits S N N O OH OMe O N H N HO N N H N O SF-1-dependent luciferase expression in HEK293T cells in vitro OMe N N N H N N O H (IC50 = 30 nM). O N N N O N H O N HO H N N N Me Me H Cl N HO H N N Me Me H Cl S N Cl Cl S N ITE (1803) CH 223191 (3858) Liarazole CITCO Calcipotriol ITE (1803) CH 223191 (3858) Liarazole CITCO Calcipotriol

www.tocris.com | 13 H OH CF3 O F Me F N CF3 S CF3 O O H H F O2 OH OH CF3 O N CF3 F F Me Me F F OH N H CF3 O S S O F N O2 O HO O N O F HO 2 O OH H H H H O N N OH S H N HO O N HO N HO HO O O N N OH HO H H N N H H S ERB 041 N N HO S N H H HO HO O O OH N Liquiritigenin OH ICI 182,780 (1047) ERB 041 HO HO ERB 041 GSK 4716 LiquiritigeninLiquiritigenin ICI 182,780ICI 182,780 (1047) (1047) F GSK GSK4716 4716 F F CF3 GSK 9027

CF3 O HO2C CF3 Tocris ProductN ListingO Series GSK GSK9027 9027 S N O O O CO2H HO C N O NH S O 2 HO C N O O 2 Ph N O O O S N N OO S S O O CO2HCO H N N O OEt O N NH S 2 O O O N NH S O POh Ph O H O O O O O H NH O O OEt S S N N Et OEt RelatedN ProductsO O Cl N O O N O O HN O O H H O TesaglitazarH H NH NH N N Et Et O NuclearCl Cl receptorPioglitazone function is also modulated by OotherHN receptors and enzymes that affect steroid hormone Tesaglitazar O HN Tesaglitazar O GSK 3787 (3961) , such as aromatase and retinoic acid 4-hydrolase. TheO aryl hydrocarbon receptor also influences the O2N PioglitazonePioglitazone F3C functionGSK of steroid 3787 (3961) hormone receptors (e.g. estrogen receptors) through a number of different mechanisms. GSK 3787 (3961) O2N O N F3C F C 2 3 SR 1664 (4409) GW 6471 (4618) Category Cat. No. Product Name Description Unit Size SR 1664 (4409) GW 6471 (4618) SR 1664 (4409) Aromatase (CYP19) GW 6471 (4618) CO2H Inhibitors 3388 Anastrozole Potent aromatase inhibitor 10 mg N CO2H CO2Et CO2H 50 mg N N NO2 4382 S LetrozoleS Potent,HO reversible non-steroidal aromataseO CO inhibitorH N 10 mg CO2Et 2 N O CO2Et 50 mg O S N NO2 S S HO O CO2H N NO2 S S HO O CO2H 2705 Liarozole Aromatase inhibitor. AlsoN blocksO retinoic acid metabolism 10 mg O N O S GC 1 (4554) O S S O 50 mg CO2H MM 11253 (3822) O O GC 1 (4554) 3278 YM 511 Potent aromatase inhibitor S S 10 mg GC 1 (4554) CO2H SMe CO2H MM 11253MM 11253 (3822) (3822) 50 mg BI 6015 Aryl Hydrocarbon Receptor (AhR) SMe SMe BI 6015BI 6015 SR 8278 (4463) Agonists 1803HO2C ITE AhR endogenous agonist BMS10 453 mg (3409) Antagonists 3858 CH 223191 AhR antagonist SR 8278 (4463) 10 mg HO2C BMS 453 (3409) SR 8278 (4463) HO2C BMS 453 (3409) 50mg N 3859 6,2ʹ,4ʹ-Trimethoxyflavone AhR antagonist O OEt 10 mg O O N N 50mg O O OEt OEt N N O N O Ligands 4393 L-KynurenineO Tryptophan catabolite; endogenous AhR ligand O 50 mg N CN O O N N N N O HO N N N Modulators 4628 DiMNF NO2 O Selective AhR modulator N 10 mg O N N N CN CN O N N HN 50 mg HO N NO2 HO N NC CN N NO2 N CN N HN HN AC 45594 O NC NC CN CN HXN 531 O AC 45594 Key Nuclear ReceptorN Related Products CN CN AC 45594 O O Cl Letrozole Cl Anastrazole HX 531 O HX 531 O Letrozole Cl Cl Anastrazole LetrozoleSID 7969543 Cl Cl Anastrazole N SID 7969543SID 7969543 S OH O H N N HO N N N O S OMe N O S H N OH OH H O H N HO N N N N O N N HO OMe H N N O N O O N OMe N N H N N H N H N HO N H O N N N H N O N Me O H Cl O N N Me N HO HO H S N N N N Cl MHe N N Cl Me Me H H Cl Me ITE (1803) CH 223191 (3858) S N Cl Cl S N LiarazoleLiarazole (2705) CITCOITE (1803) CHCalcipotriol 223191 (3858) ITE (1803) CH 223191 (3858) Aromatase inhibitor. Also blocks Aryl hydrocarbon receptorITE endogenous (1803) agonist Potent aryl hydrocarbonCH 223191 (3858)receptor antagonist LiarazoleLiarazole CITCOCITCO retinoicCalcipotriol acidCalcipotriol metabolism

14 | NUCLEAR RECEPTORS

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