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MedKoo Cat#: 563233 | Name: PhIP
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Description:

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

PhIP is a mutagen generated from high temperature cooked meats.

Chemical Structure

PhIP
PhIP
CAS#105650-23-5

Theoretical Analysis

MedKoo Cat#: 563233

Name: PhIP

CAS#: 105650-23-5

Chemical Formula: C13H12N4

Exact Mass: 224.1062

Molecular Weight: 224.27

Elemental Analysis: C, 69.62; H, 5.39; N, 24.98

Price and Availability

Size Price Availability Quantity
5mg USD 280.00
10mg USD 470.00
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Related CAS #
No Data
Synonym
PhIP;
IUPAC/Chemical Name
1-Methyl-6-phenylimidazo[4,5-b]pyridin-2-amine
InChi Key
UQVKZNNCIHJZLS-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H12N4/c1-17-11-7-10(9-5-3-2-4-6-9)8-15-12(11)16-13(17)14/h2-8H,1H3,(H2,14,15,16)
SMILES Code
NC1=NC2=NC=C(C3=CC=CC=C3)C=C2N1C
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
>3 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
2933999701
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#T9R05C08
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
PhIP (2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) is the most abundant of generation of heterocyclic amines (HCA), resulted in the cooking of meat. DNA damaging and mutagenic activities.
In vitro activity:
Notably, 2-hydroxy-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (HONH-PhIP), but not other HONH-HAAs, induced cytotoxicity. Moreover, PhIP-DNA adduct formation was 20-fold greater than adducts formed with other HONH-HAAs. Pretreatment of LNCaP cells with mefenamic acid, a specific inhibitor of sulfotransferase (SULT1A1), decreased PhIP-DNA adducts by 25%, whereas (Z)-5-(2'-hydroxybenzylidene)-2-thioxothiazolidin-4-one and pentachlorophenol, inhibitors of SULTs and N-acetyltransferases (NATs), decreased the PhIP-DNA adduct levels by 75%. Reference: Toxicol Sci. 2018 Jun 1;163(2):543-556. https://pubmed.ncbi.nlm.nih.gov/29596660/
In vivo activity:
The results showed that rats given PhIP were found to have a statistically significant (p < 0.001) reduction in the activities of CYP1A1, CYP1A2, and CYP2E1 in comparison with the control group. However, treatment with OLE enhanced their activities but not to a normal level compared with untreated groups. Administration of PhIP decreased the activities of phase II enzymes (glutathione S-transferase, UDP-glucuronyltransferase, or sulphotransferase) (p < 0.01) in comparison with the control group. The administration of OLE improved the phase II enzyme activities in animals injected with PhIP. Reference: Environ Sci Pollut Res Int. 2023 Feb;30(6):16346-16354. https://pubmed.ncbi.nlm.nih.gov/36181589/
Solvent mg/mL mM comments
Solubility
DMF 10.0 44.59
DMSO 17.5 78.03
Ethanol 15.0 66.88
Ethanol:PBS (pH 7.2) (1:3) 0.3 1.11
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 224.27 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
Formulation protocol:
1. Bellamri M, Xiao S, Murugan P, Weight CJ, Turesky RJ. Metabolic Activation of the Cooked Meat Carcinogen 2-Amino-1-Methyl-6-Phenylimidazo[4,5-b]Pyridine in Human Prostate. Toxicol Sci. 2018 Jun 1;163(2):543-556. doi: 10.1093/toxsci/kfy060. PMID: 29596660; PMCID: PMC5974788. 2. Papaioannou MD, Koufaris C, Gooderham NJ. The cooked meat-derived mammary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) elicits estrogenic-like microRNA responses in breast cancer cells. Toxicol Lett. 2014 Aug 17;229(1):9-16. doi: 10.1016/j.toxlet.2014.05.021. Epub 2014 May 28. PMID: 24877718. 3. Abulnaja K, Bakkar A, Kannan K, Al-Manzlawi AM, Kumosani T, Qari M, Moselhy S. Olive leaf (Olea europaea L. folium) extract influences liver microsomal detoxifying enzymes in rats orally exposed to 2-amino-l-methyI-6-phenyI-imidazo pyridine (PhIP). Environ Sci Pollut Res Int. 2023 Feb;30(6):16346-16354. doi: 10.1007/s11356-022-23341-w. Epub 2022 Oct 1. PMID: 36181589. 4. Zhao X, Shao Z, Zhou X, Lin Y, Guo J, Guo J, Zhang Y, Wang S. Sub-chronic exposure to PhIP induces oxidative damage and DNA damage, and disrupts the amino acid metabolism in the colons of Wistar rats. Food Chem Toxicol. 2021 Jul;153:112249. doi: 10.1016/j.fct.2021.112249. Epub 2021 May 1. PMID: 33945839.
In vitro protocol:
1. Bellamri M, Xiao S, Murugan P, Weight CJ, Turesky RJ. Metabolic Activation of the Cooked Meat Carcinogen 2-Amino-1-Methyl-6-Phenylimidazo[4,5-b]Pyridine in Human Prostate. Toxicol Sci. 2018 Jun 1;163(2):543-556. doi: 10.1093/toxsci/kfy060. PMID: 29596660; PMCID: PMC5974788. 2. Papaioannou MD, Koufaris C, Gooderham NJ. The cooked meat-derived mammary carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) elicits estrogenic-like microRNA responses in breast cancer cells. Toxicol Lett. 2014 Aug 17;229(1):9-16. doi: 10.1016/j.toxlet.2014.05.021. Epub 2014 May 28. PMID: 24877718.
In vivo protocol:
1. Abulnaja K, Bakkar A, Kannan K, Al-Manzlawi AM, Kumosani T, Qari M, Moselhy S. Olive leaf (Olea europaea L. folium) extract influences liver microsomal detoxifying enzymes in rats orally exposed to 2-amino-l-methyI-6-phenyI-imidazo pyridine (PhIP). Environ Sci Pollut Res Int. 2023 Feb;30(6):16346-16354. doi: 10.1007/s11356-022-23341-w. Epub 2022 Oct 1. PMID: 36181589. 2. Zhao X, Shao Z, Zhou X, Lin Y, Guo J, Guo J, Zhang Y, Wang S. Sub-chronic exposure to PhIP induces oxidative damage and DNA damage, and disrupts the amino acid metabolism in the colons of Wistar rats. Food Chem Toxicol. 2021 Jul;153:112249. doi: 10.1016/j.fct.2021.112249. Epub 2021 May 1. PMID: 33945839.
1: Chiavarini M, Bertarelli G, Minelli L, Fabiani R. Dietary Intake of Meat Cooking-Related Mutagens (HCAs) and Risk of Colorectal Adenoma and Cancer: A Systematic Review and Meta-Analysis. Nutrients. 2017 May 18;9(5). pii: E514. doi: 10.3390/nu9050514. Review. PubMed PMID: 28524104; PubMed Central PMCID: PMC5452244. 2: Fahrer J, Kaina B. Impact of DNA repair on the dose-response of colorectal cancer formation induced by dietary carcinogens. Food Chem Toxicol. 2017 Aug;106(Pt B):583-594. doi: 10.1016/j.fct.2016.09.029. Epub 2016 Oct 6. Review. PubMed PMID: 27693244. 3: Siddiqui S, Kadlecek S, Pourfathi M, Xin Y, Mannherz W, Hamedani H, Drachman N, Ruppert K, Clapp J, Rizi R. The use of hyperpolarized carbon-13 magnetic resonance for molecular imaging. Adv Drug Deliv Rev. 2017 Apr;113:3-23. doi: 10.1016/j.addr.2016.08.011. Epub 2016 Sep 4. Review. PubMed PMID: 27599979; PubMed Central PMCID: PMC5783573. 4: Ganesan V, Ascherman DP, Minden JS. Immunoproteomics technologies in the discovery of autoantigens in autoimmune diseases. Biomol Concepts. 2016 May 1;7(2):133-43. doi: 10.1515/bmc-2016-0007. Review. PubMed PMID: 27115324. 5: He X, Feng S. Role of Metabolic Enzymes P450 (CYP) on Activating Procarcinogen and their Polymorphisms on the Risk of Cancers. Curr Drug Metab. 2015;16(10):850-63. Review. PubMed PMID: 26652254. 6: Lazár D. Parameters of photosynthetic energy partitioning. J Plant Physiol. 2015 Mar 1;175:131-47. doi: 10.1016/j.jplph.2014.10.021. Epub 2014 Nov 29. Review. PubMed PMID: 25569797. 7: McMahon MT, Chan KW. Developing MR probes for molecular imaging. Adv Cancer Res. 2014;124:297-327. doi: 10.1016/B978-0-12-411638-2.00009-4. Review. PubMed PMID: 25287693. 8: Lee JH, Okuno Y, Cavagnero S. Sensitivity enhancement in solution NMR: emerging ideas and new frontiers. J Magn Reson. 2014 Apr;241:18-31. doi: 10.1016/j.jmr.2014.01.005. Review. PubMed PMID: 24656077; PubMed Central PMCID: PMC3967054. 9: Badal S, Delgoda R. Role of the modulation of CYP1A1 expression and activity in chemoprevention. J Appl Toxicol. 2014 Jul;34(7):743-53. doi: 10.1002/jat.2968. Epub 2014 Feb 14. Review. PubMed PMID: 24532440. 10: Suzui M, Morioka T, Yoshimi N. Colon preneoplastic lesions in animal models. J Toxicol Pathol. 2013 Dec;26(4):335-41. doi: 10.1293/tox.2013-0028. Epub 2013 Dec 26. Review. PubMed PMID: 24526805; PubMed Central PMCID: PMC3921915. 11: Glöggler S, Colell J, Appelt S. Para-hydrogen perspectives in hyperpolarized NMR. J Magn Reson. 2013 Oct;235:130-42. doi: 10.1016/j.jmr.2013.07.010. Epub 2013 Jul 24. Review. PubMed PMID: 23932399. 12: Nakai Y, Nonomura N. Inflammation and prostate carcinogenesis. Int J Urol. 2013 Feb;20(2):150-60. doi: 10.1111/j.1442-2042.2012.03101.x. Epub 2012 Jul 31. Review. PubMed PMID: 22852773. 13: Teunissen SF, Rosing H, Schinkel AH, Schellens JH, Beijnen JH. Review on the analysis of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and its phase I and phase II metabolites in biological matrices, foodstuff and beverages. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Dec 1;878(31):3199-216. doi: 10.1016/j.jchromb.2010.10.018. Epub 2010 Oct 26. Review. PubMed PMID: 21071289. 14: Ni Z, Bikadi Z, Rosenberg MF, Mao Q. Structure and function of the human breast cancer resistance protein (BCRP/ABCG2). Curr Drug Metab. 2010 Sep;11(7):603-17. Review. PubMed PMID: 20812902; PubMed Central PMCID: PMC2950214. 15: Zhang H. Hyperpolarized [(13)C]-2-hydroxyethylpropionate. 2008 Jan 31 [updated 2008 Mar 5]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK23110/ PubMed PMID: 20641315. 16: Patterson AD, Gonzalez FJ, Idle JR. Xenobiotic metabolism: a view through the metabolometer. Chem Res Toxicol. 2010 May 17;23(5):851-60. doi: 10.1021/tx100020p. Review. PubMed PMID: 20232918; PubMed Central PMCID: PMC2872059. 17: Carthew P, DiNovi M, Setzer RW. Application of the Margin of Exposure (MOE) approach to substances in food that are genotoxic and carcinogenic: example: CAS No: 105650-23-5 PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine). Food Chem Toxicol. 2010 Jan;48 Suppl 1:S98-105. doi: 10.1016/j.fct.2009.10.035. Review. PubMed PMID: 20113859. 18: Viale A, Reineri F, Santelia D, Cerutti E, Ellena S, Gobetto R, Aime S. Hyperpolarized agents for advanced MRI investigations. Q J Nucl Med Mol Imaging. 2009 Dec;53(6):604-17. Review. PubMed PMID: 20016452. 19: Ross BD, Bhattacharya P, Wagner S, Tran T, Sailasuta N. Hyperpolarized MR imaging: neurologic applications of hyperpolarized metabolism. AJNR Am J Neuroradiol. 2010 Jan;31(1):24-33. doi: 10.3174/ajnr.A1790. Epub 2009 Oct 29. Review. PubMed PMID: 19875468. 20: Wang B, Zhou SF. Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. Review. PubMed PMID: 19754423.

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