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MedKoo Cat#: 200740 | Name: Piclidenoson
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Description:

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

Piclidenoson, also known as CF101, is a specific agonist to the A3 adenosine receptor, which inhibits the development of colon carcinoma growth in cell cultures and xenograft murine models. CF101 has been shown to downregulate PKB/Akt and NF-κB protein expression level. CF101 potentiates the cytotoxic effect of 5-FU, thus preventing drug resistance. The myeloprotective effect of CF101 suggests its development as an add-on treatment to 5-FU.

Chemical Structure

Piclidenoson
Piclidenoson
CAS#152918-18-8

Theoretical Analysis

MedKoo Cat#: 200740

Name: Piclidenoson

CAS#: 152918-18-8

Chemical Formula: C18H19IN6O4

Exact Mass: 510.0513

Molecular Weight: 510.29

Elemental Analysis: C, 42.37; H, 3.75; I, 24.87; N, 16.47; O, 12.54

Price and Availability

Size Price Availability Quantity
5mg USD 400.00 2 Weeks
10mg USD 600.00 2 Weeks
25mg USD 975.00 2 Weeks
50mg USD 1,370.00 2 Weeks
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Related CAS #
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Synonym
CF101; CF-101; CF 101; ALB-7208; ALB 7208; ALB7208; IB MECA; Piclidenoson
IUPAC/Chemical Name
(2S,3S,4R,5R)-3,4-dihydroxy-5-(6-(3-iodobenzylamino)-9H-purin-9-yl)-N-methyltetrahydrofuran-2-carboxamide
InChi Key
HUJXGQILHAUCCV-MOROJQBDSA-N
InChi Code
InChI=1S/C18H19IN6O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-3-2-4-10(19)5-9/h2-5,7-8,12-14,18,26-27H,6H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1
SMILES Code
O=C([C@H]1O[C@@H](N2C=NC3=C(NCC4=CC=CC(I)=C4)N=CN=C23)[C@H](O)[C@@H]1O)NC
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, not in water
Shelf Life
>5 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
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Product Data
Product Data
Instruction
View handling instruction
Biological target:
Piclidenoson (IB-MECA) is a first-in-class, orally active and selective A3 adenosine receptor (A3AR) agonist.
In vitro activity:
The present study was designed to understand the mechanism underlying IB-MECA-induced apoptosis in human ovarian cancer cell lines. IB-MECA was capable of decreasing intracellular cyclic adenosine monophosphate (cAMP) that was the reason for the presence of functional A3 adenosine receptor on the cell lines. IB-MECA significantly reduced cell viability in a dose-dependent manner. Cytotoxicity of IB-MECA was suppressed by MRS1220, an A3 adenosine receptor antagonist. The growth inhibition effect of IB-MECA was related to the induction of cell apoptosis, which was manifested by annexin V-FITC staining, activation of caspase-3 and caspase-9, and loss of mitochondrial membrane potentials (ΔΨm). In addition, downregulation of the regulatory protein Bcl-2 and upregulation of Bax protein by IB-MECA were also observed. Reference: Tumour Biol. 2014 Nov;35(11):11027-39. https://pubmed.ncbi.nlm.nih.gov/25095978/
In vivo activity:
The memory retention score was reduced in vehicle-treated mice compared with IB-MECA-treated (p < 0.05) mice. Compared to sham-operated mice, p-ERK, GFAP and IFN-β were increased, while MAP-2 and neurofilament were reduced in vehicle-treated mice (p < 0.01 for each). IB-MECA reduced ERK phosphorylation (p < 0.01) and GFAP expression (p < 0.05), but upregulated MAP-2 and IFN-β (p < 0.01 for both), compared with vehicle. MRS1523 suppressed the effects of IB-MECA on the memory deficit, ERK phosphorylation, and on MAP-2, neurofilament, GFAP and IFN-β levels. Reference: Eur J Pharmacol. 2022 Apr 15;921:174874. https://pubmed.ncbi.nlm.nih.gov/35278404/
Solvent mg/mL mM comments
Solubility
DMF 2.0 3.92
DMSO 23.5 46.05
DMSO:PBS (pH 7.2) (1:4) 0.2 0.39
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 510.29 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. Abedi H, Aghaei M, Panjehpour M, Hajiahmadi S. Mitochondrial and caspase pathways are involved in the induction of apoptosis by IB-MECA in ovarian cancer cell lines. Tumour Biol. 2014 Nov;35(11):11027-39. doi: 10.1007/s13277-014-2396-9. Epub 2014 Aug 6. PMID: 25095978. 2. Park SS, Zhao H, Jang Y, Mueller RA, Xu Z. N6-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide confers cardioprotection at reperfusion by inhibiting mitochondrial permeability transition pore opening via glycogen synthase kinase 3 beta. J Pharmacol Exp Ther. 2006 Jul;318(1):124-31. doi: 10.1124/jpet.106.101477. Epub 2006 Apr 12. PMID: 16611852. 3. Cheng P, Zhang J, Chu Z, Liu W, Lin H, Wu Y, Zhu J. A3 adenosine receptor agonist IB-MECA reverses chronic cerebral ischemia-induced inhibitory avoidance memory deficit. Eur J Pharmacol. 2022 Apr 15;921:174874. doi: 10.1016/j.ejphar.2022.174874. Epub 2022 Mar 9. PMID: 35278404. 4. Cioato SG, Medeiros LF, Lopes BC, de Souza A, Medeiros HR, Assumpção JAF, Caumo W, Roesler R, Torres ILS. Antinociceptive and neurochemical effects of a single dose of IB-MECA in chronic pain rat models. Purinergic Signal. 2020 Dec;16(4):573-584. doi: 10.1007/s11302-020-09751-w. Epub 2020 Nov 8. PMID: 33161497; PMCID: PMC7855191.
In vitro protocol:
1. Abedi H, Aghaei M, Panjehpour M, Hajiahmadi S. Mitochondrial and caspase pathways are involved in the induction of apoptosis by IB-MECA in ovarian cancer cell lines. Tumour Biol. 2014 Nov;35(11):11027-39. doi: 10.1007/s13277-014-2396-9. Epub 2014 Aug 6. PMID: 25095978. 2. Park SS, Zhao H, Jang Y, Mueller RA, Xu Z. N6-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide confers cardioprotection at reperfusion by inhibiting mitochondrial permeability transition pore opening via glycogen synthase kinase 3 beta. J Pharmacol Exp Ther. 2006 Jul;318(1):124-31. doi: 10.1124/jpet.106.101477. Epub 2006 Apr 12. PMID: 16611852.
In vivo protocol:
1. Cheng P, Zhang J, Chu Z, Liu W, Lin H, Wu Y, Zhu J. A3 adenosine receptor agonist IB-MECA reverses chronic cerebral ischemia-induced inhibitory avoidance memory deficit. Eur J Pharmacol. 2022 Apr 15;921:174874. doi: 10.1016/j.ejphar.2022.174874. Epub 2022 Mar 9. PMID: 35278404. 2. Cioato SG, Medeiros LF, Lopes BC, de Souza A, Medeiros HR, Assumpção JAF, Caumo W, Roesler R, Torres ILS. Antinociceptive and neurochemical effects of a single dose of IB-MECA in chronic pain rat models. Purinergic Signal. 2020 Dec;16(4):573-584. doi: 10.1007/s11302-020-09751-w. Epub 2020 Nov 8. PMID: 33161497; PMCID: PMC7855191.
1: Avni I, Garzozi HJ, Barequet IS, Segev F, Varssano D, Sartani G, Chetrit N, Bakshi E, Zadok D, Tomkins O, Litvin G, Jacobson KA, Fishman S, Harpaz Z, Farbstein M, Yehuda SB, Silverman MH, Kerns WD, Bristol DR, Cohn I, Fishman P. Treatment of Dry Eye Syndrome with Orally Administered CF101 Data from a Phase 2 Clinical Trial. Ophthalmology. 2010 Mar 19. [Epub ahead of print] PubMed PMID: 20304499. 2: Bar-Yehuda S, Rath-Wolfson L, Del Valle L, Ochaion A, Cohen S, Patoka R, Zozulya G, Barer F, Atar E, Piña-Oviedo S, Perez-Liz G, Castel D, Fishman P. Induction of an antiinflammatory effect and prevention of cartilage damage in rat knee osteoarthritis by CF101 treatment. Arthritis Rheum. 2009 Oct;60(10):3061-71. PubMed PMID: 19790055. 3: Borea PA, Gessi S, Bar-Yehuda S, Fishman P. A3 adenosine receptor: pharmacology and role in disease. Handb Exp Pharmacol. 2009;(193):297-327. Review. PubMed PMID: 19639286. 4: Moral MA, Tomillero A. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Mar;30(2):149-71. PubMed PMID: 18560631. 5: Silverman MH, Strand V, Markovits D, Nahir M, Reitblat T, Molad Y, Rosner I, Rozenbaum M, Mader R, Adawi M, Caspi D, Tishler M, Langevitz P, Rubinow A, Friedman J, Green L, Tanay A, Ochaion A, Cohen S, Kerns WD, Cohn I, Fishman-Furman S, Farbstein M, Yehuda SB, Fishman P. Clinical evidence for utilization of the A3 adenosine receptor as a target to treat rheumatoid arthritis: data from a phase II clinical trial. J Rheumatol. 2008 Jan;35(1):41-8. Epub 2007 Nov 15. PubMed PMID: 18050382.

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