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71441-28-6

71441-28-6 structure
71441-28-6 structure
  • Name: TTNPB
  • Chemical Name: arotinoid acid
  • CAS Number: 71441-28-6
  • Molecular Formula: C24H28O2
  • Molecular Weight: 348.478
  • Catalog: Biochemical Inhibitor Metabolism Retinoid Receptor Inhibitor
  • Create Date: 2018-03-09 08:00:00
  • Modify Date: 2024-01-06 11:01:14
  • TTNPB is a highly potent RAR agonist. Competitive binding assays using human RARs yield IC50s of α=5.1 nM, β= 4.5 nM, and γ=9.3 nM, respectively.
Name arotinoid acid
Synonyms Ro 13-7410
Arotinoid Acid
MFCD00673917
4-[(1E)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-propen-1yl]benzoic acid
TTNPB
Tocris-0761
Arotinoic acid
TTNPB (Arotinoid Acid)
4-[(1E)-2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-1-propen-1-yl]benzoic acid
(E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid
4-[(1E)-2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-en-1-yl]benzoic acid
Lopac-T-3757
4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)propen-1-yl] benzoic acid
4-[(E)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]benzoic acid
Benzoic acid, 4-[(1E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propen-1-yl]-
Description TTNPB is a highly potent RAR agonist. Competitive binding assays using human RARs yield IC50s of α=5.1 nM, β= 4.5 nM, and γ=9.3 nM, respectively.
Related Catalog
Target

IC50: 5.1 nM (RARα), 4.5 nM (RARβ), 9.3 nM (RARγ)[1]

In Vitro TTNPB inhibits binding of [3H]tRA with IC50s of 3.8 nM, 4 nM, and 4.5 nM for human RARα, β, and γ, respectively. TTNPB competes for [3H]tRA binding to CRABPI with IC50s of 1800 nM[1].
Kinase Assay Labeled and unlabeled retinoids are added to nucleosol or cytosolic fractions in ethanol so that the total amount of ethanol added is constant in all tubes and did not exceed 2% of the incubation volume. The receptor preparations are incubated with retinoids at 47°C for 4-6 hr. Sephadex PD-10 desalting columns are used to separate bound radioligand from free radioligand after equilibrium is achieved. For competitive binding assays, varying concentrations of unlabeled competing ligand are incubated with the appropriate nucleosol or cytosol in the presence of a fixed concentration of [3H]tRA (sp act. 49.3 Ci/mmol) or [3H]9-cis RA (sp. act. 24.0 Ci/mmol). Final concentrations of [3H] tRA and [3H]9-cis RA for nuclear receptor binding assays are 5nM. Final concentrations of [3H]tRA for CRABP binding assays is 30 nM. The IC50s are calculated. For saturation kinetics, increasing concentrations of radiolabeled ligand ([3H]tRA sp. act. 49.3 Ci/mmol, [3H]TTNPB sp. act. 5.5 Ci/mmol) are added to the nucleosol of the appropriate receptor subtype in the presence (nonspecific binding) or absence (total binding) of a 100-fold molar excess of the corresponding unlabeled retinoid. Specific binding is defined as the total binding minus nonspecific binding. Saturation kinetics are calculated[1].
References

[1]. Pignatello MA, et al. Multiple factors contribute to the toxicity of the aromatic retinoid, TTNPB (Ro 13-7410): binding affinities and disposition. Toxicol Appl Pharmacol. 1997 Feb;142(2):319-27.
Density 1.1±0.1 g/cm3
Boiling Point 486.8±44.0 °C at 760 mmHg
Molecular Formula C24H28O2
Molecular Weight 348.478
Flash Point 228.6±23.1 °C
Exact Mass 348.208923
PSA 37.30000
LogP 8.62
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.579
Storage condition −20°C
Water Solubility chloroform/methanol: soluble9.80 - 10.20 mg/mL, clear, colorless to light yellow

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DH6834900
CHEMICAL NAME :
Benzoic acid, 4-(2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphth alenyl)-1-propenyl)-, (E)-
CAS REGISTRY NUMBER :
71441-28-6
LAST UPDATED :
199806
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C24-H28-O2
MOLECULAR WEIGHT :
348.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1040 ug/kg/4D-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 138,169,1996
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1250 ug/kg/25D-I
TOXIC EFFECTS :
Musculoskeletal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 40,3567,1997
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
125 ug/kg/5D-I
TOXIC EFFECTS :
Endocrine - changes in spleen weight Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 138,169,1996
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
392 ug/kg/14D-I
TOXIC EFFECTS :
Musculoskeletal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 34,91,1996 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
30 ug/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 64,43,1990
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 ug/kg
SEX/DURATION :
female 9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 64,43,1990
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
37 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
JJIND8 JNCI, Journal of the National Cancer Institute. (Washington, DC) V.61-79, 1978-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 78,533,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
75 ug/kg
SEX/DURATION :
female 8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System
REFERENCE :
JJIND8 JNCI, Journal of the National Cancer Institute. (Washington, DC) V.61-79, 1978-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 78,533,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
290 ug/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)
REFERENCE :
JJIND8 JNCI, Journal of the National Cancer Institute. (Washington, DC) V.61-79, 1978-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 78,533,1987
Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Danger
Hazard Statements H315-H319-H335-H360
Precautionary Statements P201-P261-P305 + P351 + P338-P308 + P313
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T: Toxic;
Risk Phrases R60
Safety Phrases 53-26-36/37/39-45
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS DH6834900

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