Synonym
8-CPT-cAMP; 8-(4-Chlorophenylthio)-cAMP
IUPAC/Chemical Name
(4aR,6R,7R,7aS)-6-(6-amino-8-((4-chlorophenyl)thio)-9H-purin-9-yl)-2,7-dihydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine 2-oxide
InChi Key
AAZMHPMNAVEBRE-SDBHATRESA-N
InChi Code
InChI=1S/C16H15ClN5O6PS/c17-7-1-3-8(4-2-7)30-16-21-10-13(18)19-6-20-14(10)22(16)15-11(23)12-9(27-15)5-26-29(24,25)28-12/h1-4,6,9,11-12,15,23H,5H2,(H,24,25)(H2,18,19,20)/t9-,11-,12-,15-/m1/s1
SMILES Code
O[C@H]1[C@H](N2C(SC3=CC=C(Cl)C=C3)=NC4=C(N)N=CN=C24)O[C@@]5([H])[C@@]1([H])OP(OC5)(O)=O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
471.81
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.
| 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: Sandnes D, Jacobsen FW, Refsnes M, Christoffersen T. 8-bromo-cAMP and 8-CPT- cAMP increase the density of beta-adrenoceptors in hepatocytes by a mechanism not mimicking the effect of cAMP. Pharmacol Toxicol. 1996 Jul;79(1):15-22. doi: 10.1111/j.1600-0773.1996.tb00235.x. PMID: 8841091.
2: Jiao B, Ren ZH, Liu P, Chen LJ, Shi JY, Dong Y, Ablain J, Shi L, Gao L, Hu JP, Ren RB, de Thé H, Chen Z, Chen SJ. 8-CPT-cAMP/all-trans retinoic acid targets t(11;17) acute promyelocytic leukemia through enhanced cell differentiation and PLZF/RARα degradation. Proc Natl Acad Sci U S A. 2013 Feb 26;110(9):3495-500. doi: 10.1073/pnas.1222863110. Epub 2013 Feb 4. PMID: 23382200; PMCID: PMC3587232.
3: Zhu Q, Hu JP, Jia PM, Wang ZY, Tong JH. [cAMP analogue 8-CPT-cAMP inducing differentiation in the M2b subtype of acute myeloid leukemia cell line Kasumi-1]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2008 Feb;16(1):44-7. Chinese. PMID: 18315898.
4: Chraïbi A, Schnizler M, Clauss W, Horisberger JD. Effects of 8-cpt-cAMP on the epithelial sodium channel expressed in Xenopus oocytes. J Membr Biol. 2001 Sep 1;183(1):15-23. doi: 10.1007/s00232-001-0049-6. PMID: 11547348.
5: Lorenzen M, Taylor A, Windhager EE. pH effect on osmotic response of collecting tubules to vasopressin and 8-CPT-cAMP. Am J Physiol. 1983 Aug;245(2):F188-97. doi: 10.1152/ajprenal.1983.245.2.F188. PMID: 6309011.
6: Xia X, Zhou X, Mills SL. [The effect of SP-8-CPT-cAMP on the tracer coupling between the retinal ganglion cells and amacrine cells]. Yan Ke Xue Bao. 2003 Jun;19(2):126-9. Chinese. PMID: 12870352.
7: Zhu Q, Yu Y, Jia PM, Cai X, Chen SJ, Chen Z, Wang ZY, Tong JH. [In vitro study of the effects of arsenic trioxide combined with 8-CPT-cAMP on differentiation induction in retinoic acid resistant acute promyelocytic leukemia cells]. Zhonghua Xue Ye Xue Za Zhi. 2003 Jan;24(1):6-9. Chinese. PMID: 12679001.
