Adecypenol
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00033 |
| CAS | 104493-13-2 |
| Molecular Weight | 280.28 |
| Molecular Formula | C12H16N4O4 |
| Purity | >98% |
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Description
Adecypenol is an adenosine deaminase inhibitor produced from Streptomyces sp. OM-3223.
Specification
| Synonyms | Antibiotic OM 3223; 3-Cyclopentene-1,2-diol, 5-(7,8-dihydro-8-hydroxyimidazo(4,5-d)(1,3)diazepin-3(4H)-yl)-3-(hydroxymethyl)- |
| Storage | Store at 2-8°C |
| IUPAC Name | 5-(8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol |
| Canonical SMILES | C1C(C2=C(NC=N1)N(C=N2)C3C=C(C(C3O)O)CO)O |
| InChI | InChI=1S/C12H16N4O4/c17-3-6-1-7(11(20)10(6)19)16-5-15-9-8(18)2-13-4-14-12(9)16/h1,4-5,7-8,10-11,17-20H,2-3H2,(H,13,14) |
| InChI Key | WJSAFKJWCOMTLH-UHFFFAOYSA-N |
Properties
| Appearance | Colorless needle Crystal |
| Boiling Point | 652°C at 760 mmHg |
| Melting Point | 240-245°C |
| Density | 1.81 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Ring-expanded ("Fat") nucleosides as broad-spectrum anticancer and antiviral agents
Ramachandra S Hosmane Curr Top Med Chem. 2002 Oct;2(10):1093-109. doi: 10.2174/1568026023393147.
Ring-expanded (ldauo;fat") nucleosides (RENs) described in this review are analogues of purine nucleosides containing a 5:7-fused imidazodiazepine or imidazotriazepine ring system. They are both of natural and synthetic origin, and are of chemical, biochemical, biophysical, as well as medicinal interest. The important natural RENs include coformycin, pentostatin, azepinomycin, adechlorin, and adecypenol. A majority of them are synergistic antitumor and/or antiviral antibiotics which potentiate the effects of other antitumor or antiviral compounds through inhibition of key enzymes such as adenosine deaminase or guanase which would otherwise metabolically degrade the active compounds into therapeutically less potent or totally inactive counterparts. However, despite the fact that some of the natural RENs such as coformycins are the strongest known enzyme inhibitors, they have not been proven as effective clinically as anticipated because of the extremely high toxicity associated with their use. Nevertheless, pentostatin (2'-deoxycoformycin) is a conspicuous exception as it is gaining wide attention in recent years as a clinically effective therapeutic agent against leukemias and lymphomas. Many of the recently reported synthetic RENs, by contrast, possess biological activities of their own, in particular against a wide spectrum of cancers and viruses with little toxicity to the host cells, and thus hold considerable promise as chemotherapeutic agents. The promising preliminary in vitro data concerning the effects of RENs on human cancers, in particular prostate and breast cancer cells, support their further pursuit in animal and clinical studies. RENs also carry promise against many viral infections belonging to the families of hepatitis, herpes, and respiratory infections, most notable being the hepatitis B (HBV), hepatitis C (HCV), and the West Nile (WNV) viruses.
2. Adecypenol, a unique adenosine deaminase inhibitor containing homopurine and cyclopentene rings. Taxonomy, production and enzyme inhibition
S Omura, H Ishikawa, H Kuga, N Imamura, S Taga, Y Takahashi, H Tanaka J Antibiot (Tokyo). 1986 Sep;39(9):1219-24. doi: 10.7164/antibiotics.39.1219.
Adecypenol, which exhibits potent inhibitory activity against calf intestinal adenosine deaminase (EC 3.5.4.4), was isolated from the cultured broth of Streptomyces sp. OM-3223. Adecypenol was classified as a semi-tight binding inhibitor. The Ki value against calf intestinal adenosine deaminase was 4.7 X 10(-9) M. No acute toxicity of adecypenol was observed at 100 mg/kg in mice. Adecypenol exhibited no antimicrobial activity against various bacteria and fungi at the concentration of 1.0 mg/ml.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
