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7-Hydroxyguanine

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7-Hydroxyguanine
Category Antibiotics
Catalog number BBF-01003
CAS 16870-91-0
Molecular Weight 167.13
Molecular Formula C5H5N5O2

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

7-Hydroxyguanine is an antibiotic produced by Streptomyces purpurascens. It can inhibit the growth of L1210 leukemia cells.

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Synonyms Guanine 7-oxide; Guanine 7-N-oxide
IUPAC Name 2-amino-7-hydroxy-1H-purin-6-one
Canonical SMILES C1=NC2=C(N1O)C(=O)NC(=N2)N
InChI InChI=1S/C5H5N5O2/c6-5-8-3-2(4(11)9-5)10(12)1-7-3/h1,12H,(H3,6,8,9,11)
InChI Key PIIRLHSJVLBMJN-UHFFFAOYSA-N
Appearance Colorless Needle Crystal
Boiling Point 603.8°C at 760 mmHg
Melting Point >300°C
Density 2.31 g/cm3
Solubility Soluble in Water, DMSO
1. Preparation of new 7-hydroxyguanine derivatives and their biological activities
M Kitahara, K Shinjyo, M Fukae, K Hosoe, T Shiraishi, K Ishii, K Watanabe, H Kawaharada J Antibiot (Tokyo). 1990 Apr;43(4):352-6. doi: 10.7164/antibiotics.43.352.
We prepared new 7-hydroxyguanine derivatives, 7-hydroxyguanosine 5'-monophosphate and N2-tetrahydropyranyl-7-hydroxyguanine, and compared biological activities of 7-hydroxyguanine derivatives including nucleosides acquired previously. 7-Hydroxyguanine and its nucleotide inhibited the focus formation of Rous sarcoma virus. Antitumor activities of these derivatives against mouse leukemia L1210 were not so different from one another. Anti-proliferative activities of the derivatives on various human cell lines were significantly different from one another.
2. Enzymatic conversion of 7-hydroxyguanine to its nucleosides
M Kitahara, K Ishii, T Okazaki, T Hidaka, K Watanabe J Antibiot (Tokyo). 1986 Sep;39(9):1288-90. doi: 10.7164/antibiotics.39.1288.
7-Hydroxyguanine, an antitumor purine-analog, reacted with ribose (or deoxyribose)-1-phosphate in the presence of purine nucleoside phosphorylase. We prepared 7-hydroxyguanine riboside and deoxyriboside using purine nucleoside phosphorylase from bovine spleen. Each nucleoside exhibits antitumor activity against mouse leukemia L1210 cells. The therapeutic effect of 7-hydroxyguanine deoxyriboside is superior to those of 7-hydroxyguanine and 7-hydroxyguanine riboside.
3. 7-Hydroxyguanine, a novel antimetabolite from a strain of Streptomyces purpurascens. II. Physico-chemical properties and structure determination
M Kitahara, K Ishii, H Kawaharada, K Watanabe, T Suga, T Hirata, S Nakamura J Antibiot (Tokyo). 1985 Aug;38(8):977-80. doi: 10.7164/antibiotics.38.977.
The molecular formula of a new antimetabolite produced by Streptomyces purpurascens was determined to be C5H5N5O2 by elemental analysis, FD-MS and 13C NMR. Reduction of this antimetabolite with Raney nickel yielded guanine. The antimetabolite was distinguishable from known N-hydroxyguanines by comparison of their UV spectra. The structure of the antimetabolite was finally established to be 7-hydroxyguanine by X-ray crystallography.

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