Synonym
Doridosine; 1-Methylisoguanosine
IUPAC/Chemical Name
Adenosine, N,6-didehydro-1,2,3,6-tetrahydro-1-methyl-2-oxo-
InChi Key
WRKSCDGOQXKDME-KQYNXXCUSA-N
InChi Code
InChI=1S/C11H15N5O5/c1-15-8(12)5-9(14-11(15)20)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,12,17-19H,2H2,1H3,(H,14,20)/t4-,6-,7-,10-/m1/s1
SMILES Code
OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC(C(N3C)=N)=C2NC3=O)O1)O)O
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
297.27
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: Kim YH, Nachman RJ, Pavelka L, Mosher HS, Fuhrman FA, Fuhrman GJ. Doridosine, 1-methylisoguanosine, from Anisodoris nobilis; structure, pharmacological properties and synthesis. J Nat Prod. 1981 Mar-Apr;44(2):206-14. doi: 10.1021/np50014a011. PMID: 7241154.
2: Tao PL, Yen MH, Shyu WS, Chern JW. Doridosine derivatives: binding at adenosine receptors and in vivo effects. Eur J Pharmacol. 1993 Oct 19;243(2):135-9. doi: 10.1016/0014-2999(93)90372-o. PMID: 8276062.
3: Fuhrman FA, Fuhrman GJ, Kim YH, Pavelka LA, Mosher HS. Doridosine: a new hypotensive N-methylpurine riboside from the nudibranch Anisodoris nobilis. Science. 1980 Jan 11;207(4427):193-5. doi: 10.1126/science.7350655. PMID: 7350655.
4: Liaw YC, Chern JW, Lin GS, Wang AH. Unusual conformational flexibility in N1-substituted uncommon purine nucleosides. Crystal structure of 1-allyl- isoguanosine and 1-allyl-xanthosine. FEBS Lett. 1992 Feb 3;297(1-2):4-8. doi: 10.1016/0014-5793(92)80315-8. PMID: 1551434.
5: Goya P, Martínez A. Synthesis and cytostatic screening of an SO2 analogue of doridosine. Arch Pharm (Weinheim). 1988 Feb;321(2):99-101. doi: 10.1002/ardp.19883210213. PMID: 3369933.
6: Davies LP, Baird-Lambert J, Hall JG. 1-Methylisoguanosine: interaction with central adenosine receptors and lack of antagonism of its in vivo effects by a benzodiazepine antagonist. Neuropharmacology. 1987 May;26(5):493-7. doi: 10.1016/0028-3908(87)90033-5. PMID: 3037418.
7: Fuhrman FA, Fuhrman GJ. Effects of some naturally-occurring purine ribosides on purinergic receptors in cardiac and smooth muscle. Comp Biochem Physiol C Comp Pharmacol. 1982;72(2):203-10. doi: 10.1016/0306-4492(82)90085-5. PMID: 6128140.
8: Bartlett RT, Cook AF, Holman MJ, McComas WW, Nowoswait EF, Poonian MS, Baird- Lambert JA, Baldo BA, Marwood JF. Synthesis and pharmacological evaluation of a series of analogues of 1-methylisoguanosine. J Med Chem. 1981 Aug;24(8):947-54. doi: 10.1021/jm00140a007. PMID: 7328598.
9: Harden FA, Quinn RJ, Scammells PJ. Synthesis and adenosine receptor affinity of a series of pyrazolo[3,4-d]pyrimidine analogues of 1-methylisoguanosine. J Med Chem. 1991 Sep;34(9):2892-8. doi: 10.1021/jm00113a031. PMID: 1895306.
10: Marwood JF. The cardiovascular actions of 1-methylisoguanosine. Clin Exp Pharmacol Physiol. 1981 Nov-Dec;8(6):575-84. doi: 10.1111/j.1440-1681.1981.tb00769.x. PMID: 7333043.
