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PhIP  (Synonyms: 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine)

Cat. No.: HY-118716 Pureté: 99.93%
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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. PhIP also has oestrogenic activity that could contribute to its tissue specific carcinogenicity.

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PhIP

PhIP Chemical Structure

CAS No. : 105650-23-5

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Solid + Solvent (Highly Recommended)
10 mM * 1 mL in DMSO
ready for reconstitution
 En stock
Solution
10 mM * 1 mL in DMSO En stock
Solid
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Based on 1 publication(s) in Google Scholar

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PhIP Related Antibodies

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Description

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[1][2]. DNA damaging and mutagenic activities. PhIP also has oestrogenic activity that could contribute to its tissue specific carcinogenicity[2].

In Vitro

PhIP causes widespread and largely over-lapping effects on miRNA expression. PhIP induces widespread effects via activation of oestrogen receptor alpha (ERα). Deregulation of miRNA by PhIP could potentially be an important non-DNA-damaging carcinogenic mechanism in breast cancer[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

PhIP Related Antibodies
In Vivo

Note:
Please do not refer to only one article to determine the experimental conditions. It is recommended to determine the optimal experimental conditions (animal strain, age, dosage, frequency and cycle, detection time and indicators, etc.) through preliminary experiments before the formal experiment.

PhIP (400 p.p.m. in diet) induces colon carcinogenesis in male F344 rats, progressing through defined phases: PhIP-DNA adduct formation (peaking at 1-8 weeks), subsequent crypt cell hyperproliferation (4-12 weeks), and the emergence of preneoplastic aberrant crypt foci (ACF) by 14 weeks. This sequence, upon continuous exposure for 52 weeks, results in colon carcinomas at an incidence of about 50%[3][4]
PhIP (400 p.p.m. in diet), employing an intermittent high-fat regimen, efficiently induces colon carcinogenesis in male F344 rats, with an incidence of ~45% within 60 weeks[5].
PhIP (total dose 200 mg/kg, i.g.) induces the formation of small intestinal tumors at the ages of weeks 28-40 in obese hCYP1A-db/db mice[6].

Induction of colon cancer[3][4]
Background
PhIP is metabolically activated to form DNA adducts, which induce β-catenin mutations. These mutations drive β-catenin accumulation and crypt hyperproliferation, resulting in the sequential development of dysplastic ACF, adenomas, and ultimately, colon adenocarcinoma[3][4].
Specific Modeling Methods
1.Rats: F344 rats • male • 6-week-old
Administration: 400 p.p.m. in diet • p.o. • daily for 52 weeks;
2. Rats: F344 rats • male • maintained on a high-fat diet throughout • 6-week-old
Administration: 400 p.p.m. in diet • p.o. • 2 weeks, followed by 4 weeks of high-fat diet alone, the cycle repeated 3 times, followed by the high-fat diet for 42 weeks
Note
In Modeling Method 2: After completing the 3 cycles, animals continued on the high-fat diet alone for an additional 42 weeks.
Modeling Indicators
Molecular changes: PhIP-DNA adduct formation, β-Catenin mutation (e.g., at codon 34), cytoplasmic β-catenin accumulation, increased Ki-67 level
Cellular changes: Hyperproliferation of crypt epithelial cells
Histology analysis: Dysplastic ACF, Crypt distortion


Induction of small intestinal carcinogenesis[6]
Background
The combination of PhIP-induced Apc mutation and obesity-associated DNA hypermethylation silences Apc function, driving nuclear β-catenin accumulation, crypt hyperproliferation, and ultimately the formation of dysplastic tubular adenomas in the small intestine[6].
Specific Modeling Methods
Mice: hCYP1A-db/db mice • fed with AIN93M diet • 6 week-old
Administration: 100 mg/kg • i.g. • total 2 doses, 4 days apart, starting at 6 weeks of age.
Note
Mice were continuously maintained on the AIN93M diet until the termination of the experiment (28-40 weeks after the PhIP treatment).
Modeling Indicators
Molecular changes: Upregulation of NF-κB (p65), pSTAT3, and COX2 in small intestinal tumors; nuclear β-catenin accumulation
Cellular changes: Hyperproliferation of crypt epithelial cells
Histology analysis: tubular adenomas (with dysplasia), Crypt distortion


In hCYP1A-mice, PhIP induces inflammation, epithelial cell damage, and prostatic intraepithelial neoplasia in the dorsolateral prostate lobe compared to the ventral lobe. PhIP forms DNA adducts in the prostate, PhIP also induces oxidative stress, atrophy of the acini, and inflammation of the prostate of rodents[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Essai clinique
Masse moléculaire

224.26

Formule

C13H12N4
CAS No.
Appearance

Solid

Color

White to light yellow

SMILES

NC1=NC2=NC=C(C=C2N1C)C3=CC=CC=C3
Initial Source
Livraison

Room temperature in continental US; may vary elsewhere.
Stockage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvant et solubilité
In Vitro: 

DMSO : 25 mg/mL (111.48 mM; ultrasonic and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 4.4591 mL 22.2956 mL 44.5911 mL
5 mM 0.8918 mL 4.4591 mL 8.9182 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

  • Calculateur de molarité

  • Calculateur de dilution

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass
=
Concentration
×
Volume
×
Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

×
Volume (start)

V1

=
Concentration (final)

C2

×
Volume (final)

V2

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 0.56 mg/mL (2.50 mM); Clear solution

    This protocol yields a clear solution of ≥ 0.56 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (5.6 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% Corn Oil

    Solubility: ≥ 0.56 mg/mL (2.50 mM); Clear solution

    This protocol yields a clear solution of ≥ 0.56 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (5.6 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

g

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
%
DMSO +
% 
+
%
Tween-80 +
%
Saline
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Pureté et documentation

Purity: 99.93%

SDS (419 KB)

COA (246 KB) LCMS (89 KB)

Instruction de manipulation (2659 KB)
Références

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 4.4591 mL 22.2956 mL 44.5911 mL 111.4778 mL
5 mM 0.8918 mL 4.4591 mL 8.9182 mL 22.2956 mL
10 mM 0.4459 mL 2.2296 mL 4.4591 mL 11.1478 mL
15 mM 0.2973 mL 1.4864 mL 2.9727 mL 7.4319 mL
20 mM 0.2230 mL 1.1148 mL 2.2296 mL 5.5739 mL
25 mM 0.1784 mL 0.8918 mL 1.7836 mL 4.4591 mL
30 mM 0.1486 mL 0.7432 mL 1.4864 mL 3.7159 mL
40 mM 0.1115 mL 0.5574 mL 1.1148 mL 2.7869 mL
50 mM 0.0892 mL 0.4459 mL 0.8918 mL 2.2296 mL
60 mM 0.0743 mL 0.3716 mL 0.7432 mL 1.8580 mL
80 mM 0.0557 mL 0.2787 mL 0.5574 mL 1.3935 mL
100 mM 0.0446 mL 0.2230 mL 0.4459 mL 1.1148 mL
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PhIP Related Classifications

Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

PhIP105650-23-52-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridineOthersInhibitorinhibitorinhibit

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