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Chemical Compound Review:

Oxetanocin [(2R,3R,4R)-2-(6-aminopurin- 9-yl)-4...

Synonyms: Oxetanocin A, CHEMBL116430, SureCN3417634, AC1L2HND, AR-1D2808, ...

Nishiyama, Y. et al., Hayashi, S. et al., Morita, M. et al., Maruyama, T. et al., Wu, J. et al., et al.

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of NK 84-0218

Inhibition of infectivity of human immunodeficiency virus by a novel nucleoside, oxetanocin, and related compounds [1].
A novel nucleoside with an oxetanosyl-N-glycoside has been recently isolated from a culture filtrate from Bacillus megaterium and named oxetanocin A (N. Shimada, S. Hasegawa, T. Harada, T. Tomisawa, A. Fujii, and T. Takita, J. Antibiot. 39:1623-1625, 1986) [2].
However, when directly compared for their antiviral potency against HSV-1 with their parents oxetanocin A and oxetanocin G, compounds 4a and 4b proved clearly less active [3].
In this study, we evaluated the antiherpesvirus activity of oxetanocin A and its derivatives and found that 9-(2-deoxy-2-hydroxymethyl-beta-D-erythro-oxetanosyl)guanine (OXT-G) was very potent and selective in inhibiting the replication of human cytomegalovirus (HCMV) in vitro [2].
A-73209 is a novel oxetanocin derivative with potent in vitro and in vivo activity against VZV, HSV-1, and HSV-2 [4].

High impact information on NK 84-0218

Two newly synthesized carbocyclic oxetanocin analogs, (+/-)-9-[(1 beta,2 alpha,3 beta)-2,3-bis(hydroxymethyl)-1-cyclobutyl]adenine (cyclobut-A) and (+/-)-9-[(1 beta,2 alpha,3 beta)-2,3-bis(hydroxymethyl)-1-cyclobutyl]guanine (cyclobut-G) were tested for activity against the infectivity of human immunodeficiency virus (HIV) in vitro [5].
Synthesis and antiviral activity of adenosine deaminase-resistant oxetanocin A derivatives: 2-halogeno-oxetanocin A [6].
Carbocyclic oxetanocin A(1',2'-trans-4f), the preparation of which we have already published, and G were found to be active against herpes simplex virus (type 1 and 2) in vitro, while cis-4b and cis-9b showed an in vitro antiretroviral activity against human immunodeficiency virus (type 1) [7].
By a cloning experiment it was shown that a 6.8-kb BglI-D fragment of the pOXT1 plasmid was responsible for oxetanocin A productivity and resistance [8].
Bacillus megaterium strain NK84-0218 produces a potent antiviral antibiotic, oxetanocin A, which has an oxetanosyl-N-glycoside linkage to an adenine moiety [8].

References

Inhibition of infectivity of human immunodeficiency virus by a novel nucleoside, oxetanocin, and related compounds. Seki, J., Shimada, N., Takahashi, K., Takita, T., Takeuchi, T., Hoshino, H. Antimicrob. Agents Chemother. (1989) [Pubmed]
Selective inhibition of human cytomegalovirus replication by a novel nucleoside, oxetanocin G. Nishiyama, Y., Yamamoto, N., Takahash, K., Shimada, N. Antimicrob. Agents Chemother. (1988) [Pubmed]
Carbocyclic oxetanocins lacking the C-3' methylene. Wu, J., Schneller, S.W., Seley, K.L. J. Med. Chem. (1997) [Pubmed]
Efficacy of A-73209, a potent orally active agent against VZV and HSV infections. Alder, J., Mitten, M., Norbeck, D., Marsh, K., Kern, E.R., Clement, J. Antiviral Res. (1994) [Pubmed]
Cyclobut-A and cyclobut-G, carbocyclic oxetanocin analogs that inhibit the replication of human immunodeficiency virus in T cells and monocytes and macrophages in vitro. Hayashi, S., Norbeck, D.W., Rosenbrook, W., Fine, R.L., Matsukura, M., Plattner, J.J., Broder, S., Mitsuya, H. Antimicrob. Agents Chemother. (1990) [Pubmed]
Synthesis and antiviral activity of adenosine deaminase-resistant oxetanocin A derivatives: 2-halogeno-oxetanocin A. Masuda, A., Kitagawa, M., Tanaka, A., Saito, S., Shimada, N., Ikeda, R., Hoshino, H., Daikoku, T., Nishiyama, Y. J. Antibiot. (1993) [Pubmed]
Synthesis and antiviral activities of carbocyclic oxetanocin analogues. Maruyama, T., Sato, Y., Horii, T., Shiota, H., Nitta, K., Shirasaka, T., Mitsuya, H., Honjo, M. Chem. Pharm. Bull. (1990) [Pubmed]
Cloning of oxetanocin A biosynthetic and resistance genes that reside on a plasmid of Bacillus megaterium strain NK84-0128. Morita, M., Tomita, K., Ishizawa, M., Takagi, K., Kawamura, F., Takahashi, H., Morino, T. Biosci. Biotechnol. Biochem. (1999) [Pubmed]

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