MedKoo Cat#: 581256 | Name: Dibenzo(a,i)pyrene

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dibenzo[a,i]pyrene is a polycyclic aromatic hydrocarbon (PAH) with potent carcinogenic activity. Dibenzo[a,i]pyrene was shown to induce DNA adduction, tumorigenicity as well as Ki-ras oncogene mutations in strain A/J mouse lung. Dibenzo[a,i]pyrene has been shown to be present in cigarette smoke condensate and in automobile exhaust gas in small quantities.

Chemical Structure

Dibenzo(a,i)pyrene
CAS#189-55-9

Theoretical Analysis

MedKoo Cat#: 581256

Name: Dibenzo(a,i)pyrene

CAS#: 189-55-9

Chemical Formula: C24H14

Exact Mass: 302.1096

Molecular Weight: 302.38

Elemental Analysis: C, 95.33; H, 4.67

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Synonym
Dibenzo(a,i)pyrene; DB(a,i)p; Benzo(rst)pentaphene; NSC 87521; NSC87521; NSC-87521
IUPAC/Chemical Name
Benzo(rst)pentaphene
InChi Key
TUGYIJVAYAHHHM-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H14/c1-3-7-19-15(5-1)13-17-9-10-18-14-16-6-2-4-8-20(16)22-12-11-21(19)23(17)24(18)22/h1-14H
SMILES Code
C12=CC3=CC=C4C(C5=C6C(C=CC=C6)=C4)=C3C(C=C5)=C1C=CC=C2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 302.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Masala S, Bergvall C, Westerholm R. Determination of benzo[a]pyrene and dibenzopyrenes in a Chinese coal fly ash certified reference material. Sci Total Environ. 2012 Aug 15;432:97-102. doi: 10.1016/j.scitotenv.2012.05.081. Epub 2012 Jun 20. PubMed PMID: 22728296. 2: National Toxicology Program. Polycyclic aromatic hydrocarbons: 15 Listings - benz[a]anthracene, benzo[b]fluoranthene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, dibenz[a,h]acridine, dibenz[a,j]acridine, dibenz[a,h]anthracene, 7H-dibenzo[c,g]carbazole, dibenzo[a,e]pyrene, dibenzo[a,h]pyrene, dibenzo[a,i]pyrene, dibenzo[a,l]pyrene, indeno[1,2,3-cd]pyrene, 5-methylchrysene. Rep Carcinog. 2011;12:353-61. PubMed PMID: 21863085. 3: Russell GK, Gupta RC, Vadhanam MV. Effect of phytochemical intervention on dibenzo[a,l]pyrene-induced DNA adduct formation. Mutat Res. 2015 Apr;774:25-32. doi: 10.1016/j.mrfmmm.2015.02.003. Epub 2015 Feb 25. PubMed PMID: 25794985; PubMed Central PMCID: PMC4402140. 4: Al-Anati L, Kadekar S, Högberg J, Stenius U. PCB153, TCDD and estradiol compromise the benzo[a]pyrene-induced p53-response via FoxO3a. Chem Biol Interact. 2014 Aug 5;219:159-67. doi: 10.1016/j.cbi.2014.06.007. Epub 2014 Jun 19. Erratum in: Chem Biol Interact. 2017 Apr 25;268:148. PubMed PMID: 24954032. 5: Crowell SR, Hanson-Drury S, Williams DE, Corley RA. In vitro metabolism of benzo[a]pyrene and dibenzo[def,p]chrysene in rodent and human hepatic microsomes. Toxicol Lett. 2014 Jul 3;228(1):48-55. doi: 10.1016/j.toxlet.2014.04.004. Epub 2014 Apr 21. PubMed PMID: 24769260; PubMed Central PMCID: PMC4274170. 6: Guttenplan JB, Kosinska W, Zhao ZL, Chen KM, Aliaga C, DelTondo J, Cooper T, Sun YW, Zhang SM, Jiang K, Bruggeman R, Sharma AK, Amin S, Ahn K, El-Bayoumy K. Mutagenesis and carcinogenesis induced by dibenzo[a,l]pyrene in the mouse oral cavity: a potential new model for oral cancer. Int J Cancer. 2012 Jun 15;130(12):2783-90. doi: 10.1002/ijc.26344. Epub 2011 Nov 19. PubMed PMID: 21815141; PubMed Central PMCID: PMC3596885. 7: Chen KM, Guttenplan JB, Zhang SM, Aliaga C, Cooper TK, Sun YW, DelTondo J, Kosinska W, Sharma AK, Jiang K, Bruggeman R, Ahn K, Amin S, El-Bayoumy K. Mechanisms of oral carcinogenesis induced by dibenzo[a,l]pyrene: an environmental pollutant and a tobacco smoke constituent. Int J Cancer. 2013 Sep 15;133(6):1300-9. doi: 10.1002/ijc.28152. Epub 2013 Apr 22. PubMed PMID: 23483552; PubMed Central PMCID: PMC3707976. 8: Yu S, Campiglia AD. Laser-excited time-resolved Shpol'skii spectroscopy for the direct analysis of dibenzopyrene isomers in liquid chromatography fractions. Appl Spectrosc. 2004 Dec;58(12):1385-93. PubMed PMID: 15606949. 9: Crowell SR, Amin SG, Anderson KA, Krishnegowda G, Sharma AK, Soelberg JJ, Williams DE, Corley RA. Preliminary physiologically based pharmacokinetic models for benzo[a]pyrene and dibenzo[def,p]chrysene in rodents. Toxicol Appl Pharmacol. 2011 Dec 15;257(3):365-76. doi: 10.1016/j.taap.2011.09.020. Epub 2011 Sep 29. PubMed PMID: 22001385; PubMed Central PMCID: PMC3226888. 10: Siddens LK, Larkin A, Krueger SK, Bradfield CA, Waters KM, Tilton SC, Pereira CB, Löhr CV, Arlt VM, Phillips DH, Williams DE, Baird WM. Polycyclic aromatic hydrocarbons as skin carcinogens: comparison of benzo[a]pyrene, dibenzo[def,p]chrysene and three environmental mixtures in the FVB/N mouse. Toxicol Appl Pharmacol. 2012 Nov 1;264(3):377-86. doi: 10.1016/j.taap.2012.08.014. Epub 2012 Aug 23. PubMed PMID: 22935520; PubMed Central PMCID: PMC3483092. 11: Niziolek-Kierecka M, Dreij K, Lundstedt S, Stenius U. γH2AX, pChk1, and Wip1 as potential markers of persistent DNA damage derived from dibenzo[a,l]pyrene and PAH-containing extracts from contaminated soils. Chem Res Toxicol. 2012 Apr 16;25(4):862-72. doi: 10.1021/tx200436n. Epub 2012 Mar 22. PubMed PMID: 22409540. 12: Durant JL, Lafleur AL, Busby WF Jr, Donhoffner LL, Penman BW, Crespi CL. Mutagenicity of C24H14 PAH in human cells expressing CYP1A1. Mutat Res. 1999 Oct 29;446(1):1-14. PubMed PMID: 10613181. 13: Rodríguez FA, Liu Z, Lin CH, Ding S, Cai Y, Kolbanovskiy A, Kolbanovskiy M, Amin S, Broyde S, Geacintov NE. Nuclear magnetic resonance studies of an N2-guanine adduct derived from the tumorigen dibenzo[a,l]pyrene in DNA: impact of adduct stereochemistry, size, and local DNA sequence on solution conformations. Biochemistry. 2014 Mar 25;53(11):1827-41. doi: 10.1021/bi4017044. Epub 2014 Mar 11. PubMed PMID: 24617538; PubMed Central PMCID: PMC3985812. 14: Zhang SM, Chen KM, Sun YW, Aliaga C, Lin JM, Sharma AK, Amin S, El-Bayoumy K. Simultaneous detection of deoxyadenosine and deoxyguanosine adducts in the tongue and other oral tissues of mice treated with Dibenzo[a,l]pyrene. Chem Res Toxicol. 2014 Jul 21;27(7):1199-206. doi: 10.1021/tx5001078. Epub 2014 Jun 17. PubMed PMID: 24911113; PubMed Central PMCID: PMC4106691. 15: Moore AF, Goicoechea HC, Barbosa F Jr, Campiglia AD. Parallel Factor Analysis of 4.2 K Excitation-Emission Matrices for the Direct Determination of Dibenzopyrene Isomers in Coal-Tar Samples with a Cryogenic Fiber-Optic Probe Coupled to a Commercial Spectrofluorimeter. Anal Chem. 2015;87(10):5232-9. PubMed PMID: 25902285. 16: Kropachev K, Kolbanovskiy M, Liu Z, Cai Y, Zhang L, Schwaid AG, Kolbanovskiy A, Ding S, Amin S, Broyde S, Geacintov NE. Adenine-DNA adducts derived from the highly tumorigenic Dibenzo[a,l]pyrene are resistant to nucleotide excision repair while guanine adducts are not. Chem Res Toxicol. 2013 May 20;26(5):783-93. doi: 10.1021/tx400080k. Epub 2013 Apr 24. PubMed PMID: 23570232; PubMed Central PMCID: PMC3676272. 17: Luckert C, Ehlers A, Buhrke T, Seidel A, Lampen A, Hessel S. Polycyclic aromatic hydrocarbons stimulate human CYP3A4 promoter activity via PXR. Toxicol Lett. 2013 Oct 24;222(2):180-8. doi: 10.1016/j.toxlet.2013.06.243. Epub 2013 Jul 8. PubMed PMID: 23845848. 18: Moore AF, Barbosa F Jr, Campiglia AD. Combining cryogenic fiber optic probes with commercial spectrofluorimeters for the synchronous fluorescence Shpol'skii spectroscopy of high molecular weight polycyclic aromatic hydrocarbons. Appl Spectrosc. 2014;68(1):14-25. doi: 10.1366/13-07124. PubMed PMID: 24405949. 19: Gábelová A, Poláková V, Prochazka G, Kretová M, Poloncová K, Regendová E, Luciaková K, Segerbäck D. Sustained induction of cytochrome P4501A1 in human hepatoma cells by co-exposure to benzo[a]pyrene and 7H-dibenzo[c,g]carbazole underlies the synergistic effects on DNA adduct formation. Toxicol Appl Pharmacol. 2013 Aug 15;271(1):1-12. doi: 10.1016/j.taap.2013.04.016. Epub 2013 Apr 29. PubMed PMID: 23639521. 20: DeMarini DM, Hanley NM, Warren SH, Adams LD, King LC. Association between mutation spectra and stable and unstable DNA adduct profiles in Salmonella for benzo[a]pyrene and dibenzo[a,l]pyrene. Mutat Res. 2011 Sep 1;714(1-2):17-25. doi: 10.1016/j.mrfmmm.2011.06.003. Epub 2011 Jun 13. PubMed PMID: 21689667.