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MedKoo Cat#: 563453 | Name: Cenupatide TFA
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Description:

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

Cenupatide is an urokinase plasminogen activator receptor (uPAR) inhibitor drug candidate. Cenupatide inhibits uPAR binding to the formyl peptide receptors (FPRs) can improve kidney lesions in a rat model of streptozotocin (STZ)-induced diabetes. Cenupatide was found to revert STZ-induced up-regulation of uPA levels and activity, while uPAR on podocytes and (s)uPAR were unaffected. In glomeruli, Cenupatide inhibited FPR2 expression suggesting that the drug may act downstream uPAR, and recovered the increased activity of the αvβ3 integrin/Rac-1 pathway indicating a major role of uPAR in regulating podocyte function.

Chemical Structure

Cenupatide TFA
Cenupatide TFA
CAS#unknown (TFA)

Theoretical Analysis

MedKoo Cat#: 563453

Name: Cenupatide TFA

CAS#: unknown (TFA)

Chemical Formula: C32H49F6N11O9

Exact Mass: 0.0000

Molecular Weight: 845.80

Elemental Analysis: C, 45.44; H, 5.84; F, 13.48; N, 18.22; O, 17.02

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 450.00 Ready to ship
50mg USD 850.00 Ready to ship
100mg USD 1,450.00 Ready to ship
200mg USD 2,250.00 Ready to ship
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Related CAS #
1006388-38-0 (free base) unknown (TFA)
Synonym
Cenupatide; Ac-Arg-Aib-Arg-α(Me)Phe-NH2); UPARANT; Cenupatide TFA; Cenupatide trifluoroacetic acid salt
IUPAC/Chemical Name
(S)-2-acetamido-N-(1-(((S)-1-(((S)-1-amino-2-methyl-1-oxo-3-phenylpropan-2-yl)amino)-5-guanidino-1-oxopentan-2-yl)amino)-2-methyl-1-oxopropan-2-yl)-5-guanidinopentanamide, bis(trifluoroacetic acid)
InChi Key
CWYFCAATGNBQOQ-FGIRMBSPSA-N
InChi Code
InChI=1S/C28H47N11O5.2C2HF3O2/c1-17(40)36-19(12-8-14-34-25(30)31)21(41)38-27(2,3)24(44)37-20(13-9-15-35-26(32)33)22(42)39-28(4,23(29)43)16-18-10-6-5-7-11-18;2*3-2(4,5)1(6)7/h5-7,10-11,19-20H,8-9,12-16H2,1-4H3,(H2,29,43)(H,36,40)(H,37,44)(H,38,41)(H,39,42)(H4,30,31,34)(H4,32,33,35);2*(H,6,7)/t19-,20-,28-;;/m0../s1
SMILES Code
O=C(NC(C)(C)C(N[C@@H](CCCNC(N)=N)C(N[C@](CC1=CC=CC=C1)(C)C(N)=O)=O)=O)[C@@H](NC(C)=O)CCCNC(N)=N.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F
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
2934.99.03.00
More Info
At the functional level, Cenupatide was shown to ameliorate: (a) the standard renal parameters, (b) the vascular permeability, (c) the renal inflammation, (d) the renal fibrosis including dysregulated plasminogen-plasmin system, extracellular matrix accumulation and glomerular fibrotic areas and (e) morphological alterations of the glomerulus including diseased filtration barrier. s.

Preparing Stock Solutions

The following data is based on the product molecular weight 845.80 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: Dal Monte M, Cammalleri M, Pecci V, Carmosino M, Procino G, Pini A, De Rosa M, Pavone V, Svelto M, Bagnoli P. Inhibiting the urokinase-type plasminogen activator receptor system recovers STZ-induced diabetic nephropathy. J Cell Mol Med. 2018 Nov 13. doi: 10.1111/jcmm.14004. [Epub ahead of print] PubMed PMID: 30426662. 2: Cammalleri M, Dal Monte M, Locri F, Marsili S, Lista L, De Rosa M, Pavone V, Rusciano D, Bagnoli P. Diabetic Retinopathy in the Spontaneously Diabetic Torii Rat: Pathogenetic Mechanisms and Preventive Efficacy of Inhibiting the Urokinase-Type Plasminogen Activator Receptor System. J Diabetes Res. 2017;2017:2904150. doi: 10.1155/2017/2904150. Epub 2017 Dec 31. PubMed PMID: 29464181; PubMed Central PMCID: PMC5804371. 3: Cammalleri M, Locri F, Marsili S, Dal Monte M, Pisano C, Mancinelli A, Lista L, Rusciano D, De Rosa M, Pavone V, Bagnoli P. The Urokinase Receptor-Derived Peptide UPARANT Recovers Dysfunctional Electroretinogram and Blood-Retinal Barrier Leakage in a Rat Model of Diabetes. Invest Ophthalmol Vis Sci. 2017 Jun 1;58(7):3138-3148. doi: 10.1167/iovs.17-21593. PubMed PMID: 28632880. 4: Boccella S, Panza E, Lista L, Belardo C, Ianaro A, De Rosa M, de Novellis V, Pavone V. Preclinical evaluation of the urokinase receptor-derived peptide UPARANT as an anti-inflammatory drug. Inflamm Res. 2017 Aug;66(8):701-709. doi: 10.1007/s00011-017-1051-5. Epub 2017 Apr 29. PubMed PMID: 28456844. 5: Rezzola S, Corsini M, Chiodelli P, Cancarini A, Nawaz IM, Coltrini D, Mitola S, Ronca R, Belleri M, Lista L, Rusciano D, De Rosa M, Pavone V, Semeraro F, Presta M. Inflammation and N-formyl peptide receptors mediate the angiogenic activity of human vitreous humour in proliferative diabetic retinopathy. Diabetologia. 2017 Apr;60(4):719-728. doi: 10.1007/s00125-016-4204-0. Epub 2017 Jan 13. PubMed PMID: 28083635. 6: Motta C, Lupo G, Rusciano D, Olivieri M, Lista L, De Rosa M, Pavone V, Anfuso CD. Molecular Mechanisms Mediating Antiangiogenic Action of the Urokinase Receptor-Derived Peptide UPARANT in Human Retinal Endothelial Cells. Invest Ophthalmol Vis Sci. 2016 Oct 1;57(13):5723-5735. doi: 10.1167/iovs.16-19909. PubMed PMID: 27787560. 7: Cammalleri M, Dal Monte M, Locri F, Lista L, Aronsson M, Kvanta A, Rusciano D, De Rosa M, Pavone V, André H, Bagnoli P. The Urokinase Receptor-Derived Peptide UPARANT Mitigates Angiogenesis in a Mouse Model of Laser-Induced Choroidal Neovascularization. Invest Ophthalmol Vis Sci. 2016 May 1;57(6):2600–2611. doi: 10.1167/iovs.15-18758. Erratum in: Invest Ophthalmol Vis Sci. 2016 Jul 1;57(8):3891. PubMed PMID: 27168367. 8: Dal Monte M, Rezzola S, Cammalleri M, Belleri M, Locri F, Morbidelli L, Corsini M, Paganini G, Semeraro F, Cancarini A, Rusciano D, Presta M, Bagnoli P. Antiangiogenic Effectiveness of the Urokinase Receptor-Derived Peptide UPARANT in a Model of Oxygen-Induced Retinopathy. Invest Ophthalmol Vis Sci. 2015 Apr;56(4):2392-407. doi: 10.1167/iovs.14-16323. PubMed PMID: 25766585. 9: Carriero MV, Bifulco K, Minopoli M, Lista L, Maglio O, Mele L, Di Carluccio G, De Rosa M, Pavone V. UPARANT: a urokinase receptor-derived peptide inhibitor of VEGF-driven angiogenesis with enhanced stability and in vitro and in vivo potency. Mol Cancer Ther. 2014 May;13(5):1092-104. doi: 10.1158/1535-7163.MCT-13-0949. Epub 2014 Apr 4. PubMed PMID: 24705350.