Aroclor 1254
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Basic Info
| Common Name | Aroclor 1254(F03277) |
| 2D Structure | |
| Description | Aroclor 1254 is a commercial mixture of PCBs with an average chlorine content of 54%. It is composed of mainly pentachlorobiphenyls (71.44%) and hexachlorobuphenyls (21.97%) and also includes mono-, bi-, tri, tetra-, hexa, and nonachlorinated homologs. Polychlorinated biphenyls (PCBs) are a group of 209 synthetic organic compounds with 1-10 chlorine atoms attached to biphenyl. PCBs were manufactured as commercial mixtures but banned in the 1970's because they were found to bioaccumulate in the environment and cause harmful health effects. However, PCBs do not break down readily and are still found in the environment. (L4) |
| FRCD ID | F03277 |
| CAS Number | 11097-69-1 |
| PubChem CID | 40470 |
| Formula | C12H5Cl5 |
| IUPAC Name | 1,2,3-trichloro-4-(2,3-dichlorophenyl)benzene |
| InChI Key | AUGNBQPSMWGAJE-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H5Cl5/c13-8-3-1-2-6(10(8)15)7-4-5-9(14)12(17)11(7)16/h1-5H |
| Canonical SMILES | C1=CC(=C(C(=C1)Cl)Cl)C2=C(C(=C(C=C2)Cl)Cl)Cl |
| Isomeric SMILES | C1=CC(=C(C(=C1)Cl)Cl)C2=C(C(=C(C=C2)Cl)Cl)Cl |
| Wikipedia | Aroclor 1254 |
| Synonyms |
AROCLOR 1254
52663-62-4
Chlorodiphenyl (54% Cl)
11097-69-1
UNII-88Z0CKE07W
CCRIS 900
1,1'-Biphenyl, 2,2',3,3',4-pentachloro-
PCB 82
HSDB 6357
2,2',3,3',4-pentachlorobiphenyl
|
| Classifies |
Illegal Additives
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Biphenyls and derivatives |
| Intermediate Tree Nodes | Chlorinated biphenyls |
| Direct Parent | Polychlorinated biphenyls |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Polychlorinated biphenyl - 1,2-dichlorobenzene - Halobenzene - Chlorobenzene - Aryl halide - Aryl chloride - Hydrocarbon derivative - Organochloride - Organohalogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as polychlorinated biphenyls. These are organic compounds containing at least two chlorine atoms attached to either benzene ring of the biphenyl moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 326.422 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 1 |
| Complexity | 259 |
| Monoisotopic Mass | 323.883 |
| Exact Mass | 325.88 |
| XLogP | 6.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 17 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9891 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8639 |
| P-glycoprotein Substrate | Non-substrate | 0.8147 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8786 |
| Non-inhibitor | 0.9683 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8266 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8869 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7864 |
| CYP450 2D6 Substrate | Non-substrate | 0.8237 |
| CYP450 3A4 Substrate | Non-substrate | 0.6835 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9474 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.7594 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9473 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8619 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9253 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8200 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9499 |
| Non-inhibitor | 0.8371 | |
| AMES Toxicity | Non AMES toxic | 0.9594 |
| Carcinogens | Non-carcinogens | 0.5226 |
| Fish Toxicity | High FHMT | 0.9937 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9996 |
| Honey Bee Toxicity | High HBT | 0.6475 |
| Biodegradation | Not ready biodegradable | 0.9727 |
| Acute Oral Toxicity | III | 0.8273 |
| Carcinogenicity (Three-class) | Non-required | 0.6630 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -7.3272 | LogS |
| Caco-2 Permeability | 2.0325 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7831 | LD50, mol/kg |
| Fish Toxicity | -0.3132 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.8338 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Gestational and lactational exposure to the polychlorinated biphenyl mixture Aroclor 1254 modulates retinoid homeostasis in rat offspring. | Toxicol Lett | 2014 Aug 17 | 24887809 |
| Organochlorine detection in the shed skins of snakes. | Ecotoxicol Environ Saf | 2005 Mar | 15590005 |
| Aroclor 1254 exposure reduces disease resistance and innate immune responses infasted Arctic charr. | Environ Toxicol Chem | 2005 Jan | 15683174 |
| Evaluation of beta-myrcene, alpha-terpinene and (+)- and (-)-alpha-pinene in the Salmonella/microsome assay. | Food Chem Toxicol | 2005 Feb | 15621337 |
| Effects of vitamin supplementation on PCB (Aroclor 1254)-induced changes inventral prostatic androgen and estrogen receptors. | Endocr Res | 2004 Aug | 15554362 |
| Evaluation of brominated diphenyl ether-99 toxicity with Raphidocelis subcapitata and Daphnia magna. | Environ Toxicol Chem | 2003 Sep | 12959546 |
| Studies on the metabolism of the thiofurans furfuryl mercaptan and2-methyl-3-furanthiol in rat liver. | Food Chem Toxicol | 2003 Dec | 14563401 |
| [Spore rec-assay by dry sheet medium culture plate for bacterial counts]. | Shokuhin Eiseigaku Zasshi | 2002 Feb | 11998319 |
| Developmental exposure of rats to a reconstituted PCB mixture or aroclor 1254: effects on long-term potentiation and [3H]MK-801 binding in occipital cortex and hippocampus. | Toxicol Sci | 2001 Jun | 11353141 |
| Polychlorinated biphenyls are selectively neurotoxic in the developing Spisula solidissima embryo. | J Toxicol Environ Health A | 2000 Dec 29 | 11132696 |
| Delayed effects of pre- and early-life time exposure to polychlorinated biphenyls on tadpoles of two amphibian species (Xenopus laevis and Rana temporaria). | Environ Toxicol Pharmacol | 1999 Dec | 21781936 |
| Lack of genotoxic effects of sucrose acetate isobutyrate (SAIB). | Food Chem Toxicol | 1998 Feb | 9519851 |
| Mutagenicity testing (+/-)-camphor, 1,8-cineole, citral, citronellal, (-)-menthol and terpineol with the Salmonella/microsome assay. | Mutat Res | 1998 Aug 7 | 9725999 |
| Fate and risk evaluation of persistent organic contaminants and related compounds in Victoria Harbour, Hong Kong. | Chemosphere | 1998 Apr | 9532729 |
| Michigan's fisheater cohorts: a prospective history of exposure. | Toxicol Ind Health | 1996 May-Aug | 8843566 |
| Effect of dietary casein levels on activation of promutagens in the spiral Salmonella mutagenicity assay. II. Studies with induced rat liver S9. | Mutat Res | 1996 Jun 10 | 8649465 |
| The metabolism and DNA binding of the cooked-food mutagen,2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in precision-cut rat liverslices. | Chem Biol Interact | 1995 May 19 | 7728907 |
| Uptake and depuration of PCB 77, PCB 169, and hexachlorobenzene by zebra mussels (Dreissena polymorpha). | Ecotoxicol Environ Saf | 1993 Oct | 7504612 |
| Effects of aging and caloric restriction on the genotoxicity of four carcinogens in the in vitro rat hepatocyte/DNA repair assay. | Mutat Res | 1993 Jan | 7677926 |
| Evidence that DNA repair may not be modified by age or chronic caloric restriction. | Mutat Res | 1993 Apr | 7680761 |
Targets
- General Function:
- Pyridoxal phosphate binding
- Specific Function:
- Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
- Gene Name:
- DDC
- Uniprot ID:
- P20711
- Molecular Weight:
- 53925.815 Da
- Mechanism of Action:
- PCB inhibition of aromatic-L-amino-acid decarboxylase is believed to cause decreased dopamine synthesis.
References
- ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for polychlorinated biphenyls. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp17.html
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
- Gene Name:
- SULT1E1
- Uniprot ID:
- P49888
- Molecular Weight:
- 35126.185 Da
- Mechanism of Action:
- PCBs can cause endocrine disurption by binding to estrogen sulfotransferase, which can stimulate the growth of certain cancer cells and produce other estrogenic effects, such as reproductive dysfunction.
References
- Aoki Y: Polychlorinated biphenyls, polychlorinated dibenzo-p-dioxins, and polychlorinated dibenzofurans as endocrine disrupters--what we have learned from Yusho disease. Environ Res. 2001 May;86(1):2-11. [11386736 ]
- General Function:
- Metal ion binding
- Specific Function:
- ATP-citrate synthase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Has a central role in de novo lipid synthesis. In nervous tissue it may be involved in the biosynthesis of acetylcholine.
- Gene Name:
- ACLY
- Uniprot ID:
- P53396
- Molecular Weight:
- 120838.27 Da
- Mechanism of Action:
- Aroclor 1254 inhibits ATP-citrate synthase, causing a decrease in fatty acid synthesis.
References
- Kling D, Kunkle J, Roller AS, Gamble W: Polychlorinated biphenyls: in vivo and in vitro modifications of cholesterol and fatty acid biosynthesis. J Environ Pathol Toxicol. 1978 Jul-Aug;1(6):813-28. [32219 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
- Mechanism of Action:
- Dioxin-like PCBs bind to the aryl hydrocarbon receptor, which disrupts cell function by altering the transcription of genes, mainly be inducing the expression of hepatic Phase I and Phase II enzymes, especially of the cytochrome P450 family.
References
- Safe S, Bandiera S, Sawyer T, Robertson L, Safe L, Parkinson A, Thomas PE, Ryan DE, Reik LM, Levin W, et al.: PCBs: structure-function relationships and mechanism of action. Environ Health Perspect. 1985 May;60:47-56. [2992927 ]
- General Function:
- Tyrosine 3-monooxygenase activity
- Specific Function:
- Plays an important role in the physiology of adrenergic neurons.
- Gene Name:
- TH
- Uniprot ID:
- P07101
- Molecular Weight:
- 58599.545 Da
- Mechanism of Action:
- PCB inhibition of tyrosine 3-monooxygenase is believed to cause decreased dopamine synthesis.
References
- ATSDR - Agency for Toxic Substances and Disease Registry (2000). Toxicological profile for polychlorinated biphenyls. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp17.html
- General Function:
- Polychlorinated biphenyl binding
- Specific Function:
- Binds phosphatidylcholine, phosphatidylinositol, polychlorinated biphenyls (PCB) and weakly progesterone, potent inhibitor of phospholipase A2.
- Gene Name:
- SCGB1A1
- Uniprot ID:
- P11684
- Molecular Weight:
- 9993.6 Da
- Mechanism of Action:
- PCBs will bioaccumulate by binding to receptor proteins such as uteroglobin.
References
- Troisi GM, Haraguchi K, Kaydoo DS, Nyman M, Aguilar A, Borrell A, Siebert U, Mason CF: Bioaccumulation of polychlorinated biphenyls (PCBs) and dichlorodiphenylethane (DDE) methyl sulfones in tissues of seal and dolphin morbillivirus epizootic victims. J Toxicol Environ Health A. 2001 Jan 12;62(1):1-8. [11205532 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]