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MedKoo Cat#: 530030 | Name: Tocladesine

Description:

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

Tocladesine is a cyclic adenosine monophosphate (cAMP) receptor agonist potentially for the treatment of colorectal cancer.

Chemical Structure

Tocladesine
CAS#41941-56-4

Theoretical Analysis

MedKoo Cat#: 530030

Name: Tocladesine

CAS#: 41941-56-4

Chemical Formula: C10H11ClN5O6P

Exact Mass: 363.0100

Molecular Weight: 363.65

Elemental Analysis: C, 33.03; H, 3.05; Cl, 9.75; N, 19.26; O, 26.40; P, 8.52

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
8-Cl-cAMP; ICN-1256; NSC-614491; CN1256; NSC614491; CN 1256; NSC 614491
IUPAC/Chemical Name
8-Chloroadenosine 3',5'-monophosphate
InChi Key
CLLFEJLEDNXZNR-UUOKFMHZSA-N
InChi Code
InChI=1S/C10H11ClN5O6P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,17H,1H2,(H,18,19)(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
SMILES Code
O[C@@H]([C@H](N1C(Cl)=NC2=C(N=CN=C21)N)O3)[C@H]4[C@H]3COP(O4)(O)=O
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 363.65 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: Choi KY, Cho YJ, Kim JS, Ahn YH, Hong SH. SHC1 sensitizes cancer cells to the 8-Cl-cAMP treatment. Biochem Biophys Res Commun. 2015 Aug 7;463(4):673-8. doi: 10.1016/j.bbrc.2015.05.123. PubMed PMID: 26043699. 2: Choi KY, Ahn YH, Ahn HW, Cho YJ, Hong SH. Involvement of Akt2/protein kinase B β (PKBβ) in the 8-Cl-cAMP-induced cancer cell growth inhibition. J Cell Physiol. 2013 Apr;228(4):890-902. doi: 10.1002/jcp.24240. PubMed PMID: 23018889. 3: Bajic V, Stanimirovic Z, Stevanovic J, Spremo-Potparevic B, Zivkovic L, Milicevic Z. Cytogenetic effects of 8-Cl-cAMP on human and animal chromosomes. J BUON. 2009 Jan-Mar;14(1):71-7. PubMed PMID: 19373950. 4: Han JH, Ahn YH, Choi KY, Hong SH. Involvement of AMP-activated protein kinase and p38 mitogen-activated protein kinase in 8-Cl-cAMP-induced growth inhibition. J Cell Physiol. 2009 Jan;218(1):104-12. doi: 10.1002/jcp.21573. PubMed PMID: 18756496. 5: Vucić V, Nićiforović A, Adzić M, Radojcić MB, Ruzdijić S. The combination of gamma ionizing radiation and 8-Cl-cAMP induces synergistic cell growth inhibition and induction of apoptosis in human prostate cancer cells. Invest New Drugs. 2008 Aug;26(4):309-17. PubMed PMID: 18060599. 6: Bajić V, Djelić N, Spremo-Potparević B, Zivković L, Milićević Z. A study on the genotoxic effects of 8-Cl-cAMP on human lymphocytes in vitro. Genetika. 2008 May;44(5):631-7. PubMed PMID: 18672796. 7: Cheng YM, Zhu Q, Jia PM, Hu JP. [Apoptosis of multiple myeloma cells induced by 8-Cl-cAMP in vitro]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2007 Dec;15(6):1204-7. Chinese. PubMed PMID: 18088467. 8: Janković D, Pesić M, Marković J, Kanazir S, Marković I, Rakić L, Ruzdijić S. The combination of sulfinosine and 8-Cl-cAMP induces synergistic cell growth inhibition of the human neuroblastoma cell line in vitro. Invest New Drugs. 2006 Jan;24(1):15-25. PubMed PMID: 16379041. 9: Ahn YH, Jung JM, Hong SH. 8-Cl-cAMP and its metabolite, 8-Cl-adenosine induce growth inhibition in mouse fibroblast DT cells through the same pathways: protein kinase C activation and cyclin B down-regulation. J Cell Physiol. 2004 Nov;201(2):277-85. PubMed PMID: 15334662. 10: Weissinger EM, Oettrich K, Evans C, Genieser HG, Schwede F, Dangers M, Dammann E, Kolb HJ, Mischak H, Ganser A, Kolch W. Activation of protein kinase A (PKA) by 8-Cl-cAMP as a novel approach for antileukaemic therapy. Br J Cancer. 2004 Jul 5;91(1):186-92. PubMed PMID: 15188002; PubMed Central PMCID: PMC2364761. 11: Dicitore A, Grassi ES, Caraglia M, Borghi MO, Gaudenzi G, Hofland LJ, Persani L, Vitale G. The cAMP analogs have potent anti-proliferative effects on medullary thyroid cancer cell lines. Endocrine. 2016 Jan;51(1):101-12. doi: 10.1007/s12020-015-0597-7. PubMed PMID: 25863490. 12: Grassi ES, Dicitore A, Negri I, Borghi MO, Vitale G, Persani L. 8-Cl-cAMP and PKA I-selective cAMP analogs effectively inhibit undifferentiated thyroid cancer cell growth. Endocrine. 2016 Jul 27. [Epub ahead of print] PubMed PMID: 27460006. 13: Grbovic O, Jovic V, Ruzdijic S, Pejanovic V, Rakic L, Kanazir S. 8-Cl-cAMP affects glioma cell-cycle kinetics and selectively induces apoptosis. Cancer Invest. 2002;20(7-8):972-82. PubMed PMID: 12449730. 14: Robbins SK, Houlbrook S, Priddle JD, Harris AL. 8-Cl-adenosine is an active metabolite of 8-Cl-cAMP responsible for its in vitro antiproliferative effects on CHO mutants hypersensitive to cytostatic drugs. Cancer Chemother Pharmacol. 2001 Dec;48(6):451-8. PubMed PMID: 11800025. 15: Kim SN, Ahn YH, Kim SG, Park SD, Cho-Chung YS, Hong SH. 8-Cl-cAMP induces cell cycle-specific apoptosis in human cancer cells. Int J Cancer. 2001 Jul 1;93(1):33-41. PubMed PMID: 11391618. 16: Drabek K, Pesić M, Piperski V, Ruzdijić S, Medić-Mijacević L, Pietrzkowski Z, Rakić L. 8-Cl-cAMP and tiazofurin affect vascular endothelial growth factor production and glial fibrillary acidic protein expression in human glioblastoma cells. Anticancer Drugs. 2000 Oct;11(9):765-70. PubMed PMID: 11129740. 17: Kim SN, Kim SG, Park JH, Lee MA, Park SD, Cho-Chung YS, Hong SH. Dual anticancer activity of 8-Cl-cAMP: inhibition of cell proliferation and induction of apoptotic cell death. Biochem Biophys Res Commun. 2000 Jul 5;273(2):404-10. PubMed PMID: 10873618. 18: Pesic M, Drabek K, Esler C, Ruzdijic S, Pejanovic V, Pietrzkowski Z. Inhibition of cell growth and proliferation in human glioma cells and normal human astrocytes induced by 8-Cl-cAMP and tiazofurin. Nucleosides Nucleotides Nucleic Acids. 2000 May-Jun;19(5-6):963-75. PubMed PMID: 10893715. 19: Srivastava RK, Srivastave AR, Cho-Chung YS. Synergistic effects of 8-Cl-cAMP and retinoic acids in the inhibition of growth and induction of apoptosis in ovarian cancer cells: induction of retinoic acid receptor beta. Mol Cell Biochem. 2000 Jan;204(1-2):1-9. PubMed PMID: 10718618. 20: Budillon A, Di Gennaro E, Caraglia M, Barbarulo D, Abbruzzese A, Tagliaferri P. 8-Cl-cAMP antagonizes mitogen-activated protein kinase activation and cell growth stimulation induced by epidermal growth factor. Br J Cancer. 1999 Dec;81(7):1134-41. PubMed PMID: 10584873; PubMed Central PMCID: PMC2374321.