WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H591112
CAS#: 114987-18-7
Description: Adenallene Inhibits replication and cytopathic effects of HIV in vitro.
Hodoodo Cat#: H591112
Name: Adenallene
CAS#: 114987-18-7
Chemical Formula: C9H9N5O
Exact Mass: 203.08
Molecular Weight: 203.210
Elemental Analysis: C, 53.20; H, 4.46; N, 34.47; O, 7.87
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Synonym: Adenallene;
IUPAC/Chemical Name: 2,3-Butadien-1-ol, 4-(6-amino-9H-purin-9-yl)-, (+-)-
InChi Key: TYQIYCWCVLIXPH-UHFFFAOYSA-N
InChi Code: InChI=1S/C9H9N5O/c10-8-7-9(12-5-11-8)14(6-13-7)3-1-2-4-15/h2-3,5-6,15H,4H2,(H2,10,11,12)
SMILES Code: OCC=C=CN1C=NC2=C(N)N=CN=C12
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:
Biological target: | |
In vitro activity: | |
In vivo activity: |
The following data is based on the product molecular weight 203.21 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 |
Formulation protocol: | |
In vitro protocol: | |
In vivo protocol: |
1: Egron D, Périgaud C, Gosselin G, Aubertin AM, Gatanaga H, Mitsuya H, Zemlicka J, Imbach JL. Increase of the adenallene anti-HIV activity in cell culture using its bis(tBuSATE) phosphotriester derivative. Bioorg Med Chem Lett. 2002 Jan 21;12(2):265-6. PubMed PMID: 11755368.
2: Winter H, Maeda Y, Uchida H, Mitsuya H, Zemlicka J. Phosphodiester amidates of unsaturated nucleoside analogues: synthesis and anti-HIV activity. J Med Chem. 1997 Jul 4;40(14):2191-5. PubMed PMID: 9216838.
3: Winter H, Maeda Y, Mitsuya H, Zemlicka J. Phosphodiester amidates of allenic nucleoside analogues: anti-HIV activity and possible mechanism of action. J Med Chem. 1996 Aug 16;39(17):3300-6. PubMed PMID: 8765513.
4: Jones BC, Silverton JV, Simons C, Megati S, Nishimura H, Maeda Y, Mitsuya H, Zemlicka J. Synthesis, absolute configuration, and enantioselectivity of antiretroviral effect of (R)-(-)- and (S)-(+)-cytallene. Lipase-catalyzed enantioselective acylations of (+/-)-N4-acylcytallenes. J Med Chem. 1995 Apr 14;38(8):1397-405. PubMed PMID: 7731024.
5: Kessel D, Zemlicka J. Accumulation and metabolism of adenallene by murine leukemia L1210 cells. Arch Biochem Biophys. 1994 Jan;308(1):222-5. PubMed PMID: 8311456.
6: Megati S, Goren Z, Silverton JV, Orlina J, Nishimura H, Shirasaki T, Mitsuya H, Zemlicka J. (R)-(-)- and (S)-(+)-adenallene: synthesis, absolute configuration, enantioselectivity of antiretroviral effect, and enzymic deamination. J Med Chem. 1992 Oct 30;35(22):4098-104. Erratum in: J Med Chem 1993 Mar 5;36(5):634. PubMed PMID: 1304169.
7: Kierdaszuk B, Bohman C, Ullman B, Eriksson S. Substrate specificity of human deoxycytidine kinase toward antiviral 2',3'-dideoxynucleoside analogs. Biochem Pharmacol. 1992 Jan 22;43(2):197-206. PubMed PMID: 1739408.
8: Kochetkova MV, Tsytovich AV, Mitsner BI. A convenient approach to the synthesis of nucleic acid bases allenic derivatives, possessing anti-HIV activity. Nucleic Acids Symp Ser. 1991;(24):233. PubMed PMID: 1841305.
9: Khorlin AA, Smirnov IP, Kochetkova SV, Tsilevich TL, Shchaveleva IL. [Compounds similar to acyclovir. IV. A convenient method of synthesizing adenallene]. Bioorg Khim. 1989 Apr;15(4):530-3. Russian. PubMed PMID: 2751711.
10: Hayashi S, Phadtare S, Zemlicka J, Matsukura M, Mitsuya H, Broder S. Adenallene and cytallene: acyclic-nucleoside analogues that inhibit replication and cytopathic effect of human immunodeficiency virus in vitro. Proc Natl Acad Sci U S A. 1988 Aug;85(16):6127-31. PubMed PMID: 3261865; PubMed Central PMCID: PMC281918.