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  • Product Name: CD437
  • Price: $600.0/100mg $1100.0/250mg $2100.0/1g
  • Purity: 98.0%
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125316-60-1

125316-60-1 structure
125316-60-1 structure
  • Name: CD437
  • Chemical Name: 6-[3-(1-adamantyl)-4-hydroxyphenyl]naphthalene-2-carboxylic acid
  • CAS Number: 125316-60-1
  • Molecular Formula: C27H26O3
  • Molecular Weight: 398.493
  • Catalog: Signaling Pathways Metabolic Enzyme/Protease RAR/RXR
  • Create Date: 2016-09-22 14:17:47
  • Modify Date: 2024-01-12 16:19:15
  • CD437 is a selective Retinoic Acid Receptor γ (RARγ) agonist.
Name 6-[3-(1-adamantyl)-4-hydroxyphenyl]naphthalene-2-carboxylic acid
Synonyms 6-[3-(Adamantan-1-yl)-4-hydroxyphenyl]-2-naphthoic acid
O-Desmethyl Adapalene
2-Naphthalenecarboxylic acid, 6-(4-hydroxy-3-tricyclo[3.3.1.1]dec-1-ylphenyl)-
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
Description CD437 is a selective Retinoic Acid Receptor γ (RARγ) agonist.
Related Catalog
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.
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
Storage condition -20°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QJ1975900
CHEMICAL NAME :
2-Naphthalenecarboxylic acid, 6-(4-hydroxy-3-tricyclo(3.3.1.1(3,7))dec-1-ylphenyl)-
CAS REGISTRY NUMBER :
125316-60-1
LAST UPDATED :
199806
DATA ITEMS CITED :
2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
15 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 53,158,1996
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
15 mg/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 53,158,1996
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Safety Phrases S22
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS QJ1975900
106685-43-2 structure

106685-43-2

~76%

125316-60-1 structure

125316-60-1
Literature: Charpentier; Bernardon; Eustache; Millois; Martin; Michel; Shroot Journal of Medicinal Chemistry, 1995 , vol. 38, # 26 p. 4993 - 5006
106-41-2 structure

106-41-2

~%

125316-60-1 structure

125316-60-1
Literature: Journal of Medicinal Chemistry, , vol. 38, # 26 p. 4993 - 5006
768-95-6 structure

768-95-6

~%

125316-60-1 structure

125316-60-1
Literature: Journal of Medicinal Chemistry, , vol. 38, # 26 p. 4993 - 5006
104224-68-2 structure

104224-68-2

~%

125316-60-1 structure

125316-60-1
Literature: Journal of Medicinal Chemistry, , vol. 38, # 26 p. 4993 - 5006
104224-85-3 structure

104224-85-3

~%

125316-60-1 structure

125316-60-1
Literature: Journal of Medicinal Chemistry, , vol. 38, # 26 p. 4993 - 5006
106685-42-1 structure

106685-42-1

~%

125316-60-1 structure

125316-60-1
Literature: Journal of Medicinal Chemistry, , vol. 38, # 26 p. 4993 - 5006

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