![6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthalenecarboxylicacid structure, CAS 125316-60-1](/structures/100000/89748_1_125316_60_1.png)
CAS Number125316-60-1
Synonyms6-[3-(Adamantan-1-yl)-4-hydroxyphenyl]-2-naphthoic acid; O-Desmethyl Adapalene; 6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid AHPN; AHPN; 6-[4-hydroxy-3-(tricyclo[3.3.1.1]dec-1-yl)phenyl]naphthalene-2-carboxylic acid; Cd 437; CD437
Molecular FormulaC27H26O3
Molecular Weight398.49
Purity≥98 (HPLC)%
Density1.3±0.1 g/cm3
Boiling Point595.0±50.0 °C at 760 mmHg
Melting Point271.6-276 °C
Appearancesolid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 125316-60-1 |
| Catalog No. | 2A-9089748 |
| Chinese Name | CD 437 |
| Synonyms | 6-[3-(Adamantan-1-yl)-4-hydroxyphenyl]-2-naphthoic acid; O-Desmethyl Adapalene; 6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid AHPN; AHPN; 6-[4-hydroxy-3-(tricyclo[3.3.1.1]dec-1-yl)phenyl]naphthalene-2-carboxylic acid; Cd 437; CD437 |
| Molecular Formula | C27H26O3 |
| Molecular Weight | 398.49 |
| Purity | ≥98 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 595.0±50.0 °C at 760 mmHg |
| Melting Point | 271.6-276 °C |
| Appearance | solid |
| Storage Condition | -20°C |
| Application | CD437 is a selective retinoic acid receptor γ (RARγ) agonist. |
| PubChem ID | 24724445 |
| MDL Number | MFCD03106506 |
| SMILES | OC(=O)c1ccc2cc(ccc2c1)-c3ccc(O)c(c3)C45CC6CC(CC(C6)C4)C5 |
| InChI | 1S/C27H26O3/c28-25-6-5-22(20-1-2-21-11-23(26(29)30)4-3-19(21)10-20)12-24(25)27-13-16-7-17(14-27)9-18(8-16)15-27/h1-6,10-12,16-18,28H,7-9,13-15H2,(H,29,30) |
| InChI Key | LDGIHZJOIQSHPB-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/89748_1_125316_60_1.pdf |
| Bioactivity | CD437 is a selective Retinoic Acid Receptor γ (RARγ) agonist. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> RAR/RXR Research Areas >> Cancer Target Retinoic Acid Receptor γ (RARγ)[1] In Vitro CD437 is a selective RARγ agonist. Growth inhibition by CD437 in these lung cancer cell lines is apparent after 2 days of treatment with 10 μM CD437. Dose-response experiments demonstrate that CD437 reduces the numbers of H460, SK-MES-1, A549, and H292 cells with 50% inhibitory values of approximately 0.5, 0.4, 3, and 0.85 μM, respectively[1]. Treatment for 72 h with CD437 causes a strong dose-dependent growth inhibition in all melanoma cell lines. At a concentration of 5 μM CD437, only about 5 to 25% of the cells remain viable after 3 d. The concentrations of CD437 required for 50% growth inhibition (IC50) range from 10 μM for MeWo to 0.1 μM for SK-Mel-23 showing the highest sensitivity[2]. In Vivo Tumors in CD437-treated mice stop growing, an effect that becomes already statistically significant (P<0.01) at day 13, 3 d after first administration of CD437, and is maintained for more than 3 wk after discontinuation of treatment. Further histologic analysis demonstrates marked c-fos mRNA levels at the tumor-stroma edge in CD437-treated tumors[2]. Cell Assay For morphological analysis, cells are treated with 10 μM CD437, trypsinized, washed with phosphate-buffered saline (PBS), fixed with 3.7% paraformaldehyde, and stained with 50 μg of 4,6-diamidino-2-phenylindole (DAPI) per mL containing 100 μg of DNase-free RNase A per mL to visualize the nuclei. Stained cells are examined by fluorescence microscopy. For the terminal deoxynucleotidyl transferase (TdT) assay, cells are treated with or without 10 μM CD437. After treatment, cells are trypsinized, washed with PBS, fixed in 1% formaldehyde in PBS, washed with PBS, resuspended in 70% ice-cold ethanol, and immediately stored at -20°C overnight. Cells are then labeled with biotin-16-dUTP by terminal transferase and stained with avidin-FITC (fluorescein isothiocyanate). The labeled cells are analyzed with a flow cytometer[1]. Animal Admin Male Swiss-nu/nu mice weighing 20 to 25 g are used in this study. Mice are kept under sterile conditions at 24 to 26°C room temperature, 50% relative humidity, and 12 h light-dark rhythm in laminar flow shelves and are supplied with autoclaved food and bedding. For treatment of melanoma xenografts, previously established MeWo melanoma tumors of 1 to 2 mm in diameter are implanted into the right flank of animals. After tumor growth for 10 d, groups of mice (n=8) are either treated with saline p.o. or are injected intratumorally for 3 wk or are fed with various concentrations of CD437 (10 mg/kg/body weight and 30 mg/kg/body weight). In addition, tumors of a fifth group are injected with CD437 (10 mg/kg/body weight) each day. Mice are visited daily and growing tumors are measured twice weekly with a caliperlike instrument[2]. References [1]. Li Y, et al. Molecular determinants of AHPN (CD437)-induced growth arrest and apoptosis in human lung cancer cell lines. Mol Cell Biol. 1998 Aug;18(8):4719-31. [2]. Schadendorf D, et al. Treatment of melanoma cells with the synthetic retinoid CD437 induces apoptosis via activation of AP-1 in vitro, and causes growth inhibition in xenografts in vivo. J Cell Biol. 1996 Dec;135(6 Pt 2):1889-98. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 595.0±50.0 °C at 760 mmHg Melting Point 271.6-276ºC Molecular Formula C27H26O3 Molecular Weight 398.493 Flash Point 327.7±26.6 °C Exact Mass 398.188202 PSA 57.53000 LogP 7.45 Vapour Pressure 0.0±1.8 mmHg at 25°C Index of Refraction 1.689 InChIKey LDGIHZJOIQSHPB-UHFFFAOYSA-N SMILES O=C(O)c1ccc2cc(-c3ccc(O)c(C45CC6CC(CC(C6)C4)C5)c3)ccc2c1 Storage condition -20°C |
| Use of | CD437 is a selective Retinoic Acid Receptor γ (RARγ) agonist. Properties Name 6-[3-(1-adamantyl)-4-hydroxyphenyl]naphthalene-2-carboxylic acid Synonym More Synonyms CD437 Biological Activity Description CD437 is a selective Retinoic Acid Receptor γ (RARγ) agonist. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> RAR/RXR Research Areas >> Cancer Retinoic Acid Receptor γ (RARγ)[1] In Vivo Tumors in CD437-treated mice stop growing, an effect that becomes already statistically significant (P<0.01) at day 13, 3 d after first administration of CD437, and is maintained for more than 3 wk after discontinuation of treatment. Further histologic analysis demonstrates marked c-fos mRNA levels at the tumor-stroma edge in CD437-treated tumors[2]. References [1]. Li Y, et al. Molecular determinants of AHPN (CD437)-induced growth arrest and apoptosis in human lung cancer cell lines. Mol Cell Biol. 1998 Aug;18(8):4719-31. [2]. Schadendorf D, et al. Treatment of melanoma cells with the synthetic retinoid CD437 induces apoptosis via activation of AP-1 in vitro, and causes growth inhibition in xenografts in vivo. J Cell Biol. 1996 Dec;135(6 Pt 2):1889-98. Chemical & Physical Properties Molecular Formula C27H26O3 Exact Mass 398.188202 PSA 57.53000 Index of Refraction 1.689 InChIKey LDGIHZJOIQSHPB-UHFFFAOYSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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