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

MedKoo CAT#: 562896

CAS#: 41270-96-6

Description: 4-IPP is a cell permeable, potent macrophage migration inhibitory factor (MIF) antagonist that covalently modifies MIF N-terminal proline.


Chemical Structure

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4-IPP
CAS# 41270-96-6

Theoretical Analysis

MedKoo Cat#: 562896
Name: 4-IPP
CAS#: 41270-96-6
Chemical Formula: C10H7IN2
Exact Mass: 281.9654
Molecular Weight: 282.08
Elemental Analysis: C, 42.58; H, 2.50; I, 44.99; N, 9.93

Price and Availability

Size Price Availability Quantity
5.0mg USD 300.0 2 Weeks
25.0mg USD 770.0 2 Weeks
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Synonym: 4-IPP; 4 IPP; 4IPP;

IUPAC/Chemical Name: 4-Iodo-6-phenyl-pyrimidine

InChi Key: ZTCJXHNJVLUUMR-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H7IN2/c11-10-6-9(12-7-13-10)8-4-2-1-3-5-8/h1-7H

SMILES Code: IC1=NC=NC(C2=CC=CC=C2)=C1

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

Preparing Stock Solutions

The following data is based on the product molecular weight 282.08 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

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1: Bozzi F, Mogavero A, Varinelli L, Belfiore A, Manenti G, Caccia C, Volpi CC, Beznoussenko GV, Milione M, Leoni V, Gloghini A, Mironov AA, Leo E, Pilotti S, Pierotti MA, Bongarzone I, Gariboldi M. MIF/CD74 axis is a target for novel therapies in colon carcinomatosis. J Exp Clin Cancer Res. 2017 Jan 23;36(1):16. doi: 10.1186/s13046-016-0475-z. PubMed PMID: 28114961; PubMed Central PMCID: PMC5260021.

2: Johler SM, Fuchs J, Seitz G, Armeanu-Ebinger S. Macrophage migration inhibitory factor (MIF) is induced by cytotoxic drugs and is involved in immune escape and migration in childhood rhabdomyosarcoma. Cancer Immunol Immunother. 2016 Dec;65(12):1465-1476. Epub 2016 Sep 15. PubMed PMID: 27629595.

3: Guo D, Guo J, Yao J, Jiang K, Hu J, Wang B, Liu H, Lin L, Sun W, Jiang X. D-dopachrome tautomerase is over-expressed in pancreatic ductal adenocarcinoma and acts cooperatively with macrophage migration inhibitory factor to promote cancer growth. Int J Cancer. 2016 Nov 1;139(9):2056-67. doi: 10.1002/ijc.30278. Epub 2016 Jul 28. PubMed PMID: 27434219.

4: Zheng Y, Wang Q, Li T, Qian J, Lu Y, Li Y, Bi E, Reu F, Qin Y, Drazba J, Hsi E, Yang J, Cai Z, Yi Q. Role of Myeloma-Derived MIF in Myeloma Cell Adhesion to Bone Marrow and Chemotherapy Response. J Natl Cancer Inst. 2016 Jul 5;108(11). doi: 10.1093/jnci/djw131. Print 2016 Nov. PubMed PMID: 27381622; PubMed Central PMCID: PMC5241902.

5: Waigel S, Rendon BE, Lamont G, Richie J, Mitchell RA, Yaddanapudi K. MIF inhibition reverts the gene expression profile of human melanoma cell line-induced MDSCs to normal monocytes. Genom Data. 2016 Jan 9;7:240-2. doi: 10.1016/j.gdata.2015.12.025. eCollection 2016 Mar. PubMed PMID: 26981417; PubMed Central PMCID: PMC4778657.

6: Subbannayya T, Leal-Rojas P, Barbhuiya MA, Raja R, Renuse S, Sathe G, Pinto SM, Syed N, Nanjappa V, Patil AH, Garcia P, Sahasrabuddhe NA, Nair B, Guerrero-Preston R, Navani S, Tiwari PK, Santosh V, Sidransky D, Prasad TS, Gowda H, Roa JC, Pandey A, Chatterjee A. Macrophage migration inhibitory factor - a therapeutic target in gallbladder cancer. BMC Cancer. 2015 Nov 4;15:843. doi: 10.1186/s12885-015-1855-z. PubMed PMID: 26530123; PubMed Central PMCID: PMC4632274.

7: Dickerhof N, Schindler L, Bernhagen J, Kettle AJ, Hampton MB. Macrophage migration inhibitory factor (MIF) is rendered enzymatically inactive by myeloperoxidase-derived oxidants but retains its immunomodulatory function. Free Radic Biol Med. 2015 Dec;89:498-511. doi: 10.1016/j.freeradbiomed.2015.09.009. Epub 2015 Oct 8. PubMed PMID: 26453918.

8: Varinelli L, Caccia D, Volpi CC, Caccia C, De Bortoli M, Taverna E, Gualeni AV, Leoni V, Gloghini A, Manenti G, Bongarzone I. 4-IPP, a selective MIF inhibitor, causes mitotic catastrophe in thyroid carcinomas. Endocr Relat Cancer. 2015 Oct;22(5):759-75. doi: 10.1530/ERC-15-0299. Epub 2015 Jul 23. PubMed PMID: 26206776.

9: Rajasekaran D, Zierow S, Syed M, Bucala R, Bhandari V, Lolis EJ. Targeting distinct tautomerase sites of D-DT and MIF with a single molecule for inhibition of neutrophil lung recruitment. FASEB J. 2014 Nov;28(11):4961-71. doi: 10.1096/fj.14-256636. Epub 2014 Jul 11. PubMed PMID: 25016026; PubMed Central PMCID: PMC4200328.

10: Kindt N, Laurent G, Nonclercq D, Journé F, Ghanem G, Duvillier H, Gabius HJ, Lechien J, Saussez S. Pharmacological inhibition of macrophage migration inhibitory factor interferes with the proliferation and invasiveness of squamous carcinoma cells. Int J Oncol. 2013 Jul;43(1):185-93. doi: 10.3892/ijo.2013.1944. Epub 2013 May 16. PubMed PMID: 23677331.

11: Chiha M, Merouani S, Hamdaoui O, Baup S, Gondrexon N, Pétrier C. Modeling of ultrasonic degradation of non-volatile organic compounds by Langmuir-type kinetics. Ultrason Sonochem. 2010 Jun;17(5):773-82. doi: 10.1016/j.ultsonch.2010.03.007. Epub 2010 Mar 27. PubMed PMID: 20388590.

12: Jauhiainen M, Mönkkönen H, Räikkönen J, Mönkkönen J, Auriola S. Analysis of endogenous ATP analogs and mevalonate pathway metabolites in cancer cell cultures using liquid chromatography-electrospray ionization mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Oct 1;877(27):2967-75. doi: 10.1016/j.jchromb.2009.07.010. Epub 2009 Jul 14. PubMed PMID: 19665949.

13: Winner M, Meier J, Zierow S, Rendon BE, Crichlow GV, Riggs R, Bucala R, Leng L, Smith N, Lolis E, Trent JO, Mitchell RA. A novel, macrophage migration inhibitory factor suicide substrate inhibits motility and growth of lung cancer cells. Cancer Res. 2008 Sep 15;68(18):7253-7. doi: 10.1158/0008-5472.CAN-07-6227. PubMed PMID: 18794110; PubMed Central PMCID: PMC2726006.

4-IPP

5.0mg / USD 300.0