Probestin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02063 |
| CAS | 123652-87-9 |
| Molecular Weight | 502.60 |
| Molecular Formula | C26H38N4O6 |
| Purity | >98% |
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Description
Probestin is an aminopeptidase M inhibitor produced by Str. azureus MH 663-2F6.
Specification
| Synonyms | 1-(1-(N-(3-Amino-2-hydroxy-1-oxo-4-phenylbutyl)leucyl)prolyl)proline; Proline, 1-(1-(N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)leucyl)prolyl)- |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-1-[(2S)-1-[(2S)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid |
| Canonical SMILES | CC(C)CC(C(=O)N1CCCC1C(=O)N2CCCC2C(=O)O)NC(=O)C(C(CC3=CC=CC=C3)N)O |
| InChI | InChI=1S/C26H38N4O6/c1-16(2)14-19(28-23(32)22(31)18(27)15-17-8-4-3-5-9-17)24(33)29-12-6-10-20(29)25(34)30-13-7-11-21(30)26(35)36/h3-5,8-9,16,18-22,31H,6-7,10-15,27H2,1-2H3,(H,28,32)(H,35,36)/t18-,19+,20+,21+,22+/m1/s1 |
| InChI Key | CEQMEILRVSCKGT-FXTUREPZSA-N |
Properties
| Appearance | Colorless Powder |
| Boiling Point | 841.3±65.0°C at 760 mmHg |
| Melting Point | 168-170°C |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Evaluation of 99mTc-probestin for imaging APN expressing tumors by SPECT
Gopal Pathuri, Andria F Hedrick, Vibhudutta Awasthi, Michael A Ihnat, Hariprasad Gali Bioorg Med Chem Lett. 2013 Sep 15;23(18):5049-52. doi: 10.1016/j.bmcl.2013.07.046. Epub 2013 Jul 29.
Aminopeptidase N (APN) is known to play important roles in tumor angiogenesis, tumor cell invasion, and metastasis. Thus, APN is an attractive biomarker for imaging tumor angiogenesis. Here we report results obtained from biodistribution and single photon emission computed tomography (SPECT) imaging studies of a technetium-99m labeled probestin (a potent APN inhibitor) conjugate containing a tripeptide, Asp-DAP-Cys (DAP=2,3-diaminopropionic acid), chelator and a 8-amino-3,6-dioxaoctanoic acid (PEG2) linker conducted in nude mice xenografted with HT-1080 human fibrosarcoma tumors (APN-positive tumors). These results collectively demonstrate that (99m)Tc-probestin uptake by tumors and other APN expressing tissues in vivo is specific and validate the use of probestin as a vector for targeting APN in vivo.
2. Solid phase synthesis and biological evaluation of probestin as an angiogenesis inhibitor
Gopal Pathuri, Jessica E Thorpe, Bryan C Disch, Lora C Bailey-Downs, Michael A Ihnat, Hariprasad Gali Bioorg Med Chem Lett. 2013 Jun 15;23(12):3561-4. doi: 10.1016/j.bmcl.2013.04.031. Epub 2013 Apr 23.
Probestin is a potent aminopeptidase N (APN) inhibitor originally isolated from the bacterial culture broth. Here, we report probestin synthesis by solid phase peptide synthesis (SPPS) method and evaluated its activity to inhibit angiogenesis using a chicken embryo chorioallantoic membrane (CAM) assay and a CAM tumor xenograft model. Results from these studies demonstrate that probestin inhibits the angiogenic activity and tumor growth.
3. Evaluation of (99m)Tc-probestin SPECT as a novel technique for noninvasive imaging of kidney aminopeptidase N expression
Gopal Pathuri, Venkateshwar Madka, Andria F Hedrick, Stanley A Lightfoot, Vibhudutta Awasthi, Benjamin D Cowley Jr, Chinthalapally V Rao, Hariprasad Gali Mol Pharm. 2014 Aug 4;11(8):2948-53. doi: 10.1021/mp5002872. Epub 2014 Jul 10.
Aminopeptidase N (APN; CD13; EC 3.4.11.2) is a zinc-dependent membrane-bound exopeptidase that catalyzes the removal of N-terminal amino acids from peptides. APN is known to be highly expressed on renal cortical proximal tubules. APN expression levels are markedly decreased under the influence of nephrotoxins and in the tumor regions of renal cancers. Thus, molecular imaging of kidney APN expression could provide pathophysiological information about kidneys noninvasively. Probestin is a potent APN inhibitor and binds to APN. Abdominal SPECT imaging was conducted at 1 h postinjection of (99m)Tc-probestin in a group of 12 UPII-SV40T transgenic and wild-type mice. UPII-SV40T mice spontaneously develop urothelial carcinoma in situ and invasive transitional cell carcinoma (TCC) that invade kidneys. Histopathology and immunohistochemistry analysis were used to confirm the presence of tumor and to evaluate APN expression in kidney. Radioactivity in normal tissue regions of renal cortex was clearly visible in SPECT images, whereas tumor regions of renal cortex displayed significantly lower or no radioactivity uptake. Histopathological analysis of kidney sections showed normal morphology for both renal pelvic and cortical regions in wild-type mice and abnormal morphology in some transgenic mice. Proliferating cell nuclear antigen staining confirmed the presence of tumor in those abnormal regions. Immunohistochemical analysis of kidney sections using anti-CD13 antibody showed significantly lower APN expression in tumor regions compared to normal regions. Results obtained in this study demonstrate the potential use of (99m)Tc-probestin SPECT as a novel technique for noninvasive imaging of kidney APN expression.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
