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Safracin A

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Safracin A
Category Antibiotics
Catalog number BBF-02218
CAS 87578-98-1
Molecular Weight 524.61
Molecular Formula C28H36N4O6
Purity >98%

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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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

Safracin A is produced by the strain of Pseudomonas fluorescens A22 (IFO 14128). It has anti-gram-positive bacteria, gram-negative bacteria and anti-tumor effect.

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Synonyms Y-16760; 2-Amino-N-[(1-hydroxy-2,11-dimethoxy-3,12,16-trimethyl-10,13-dioxo-6,7,9,10,13,14,14a,15-octahydro-5H-6,15-epiminoisoquinolino[3,2-b][3]benzazocin-9-yl)methyl]propanimidic acid
IUPAC Name (2S)-2-amino-N-[[(1S,2S,10R,13R)-19-hydroxy-7,18-dimethoxy-6,17,21-trimethyl-5,8-dioxo-11,21-diazapentacyclo[11.7.1.02,11.04,9.015,20]henicosa-4(9),6,15(20),16,18-pentaen-10-yl]methyl]propanamide
Canonical SMILES CC1=CC2=C(C3C4CC5=C(C(N4CC(C2)N3C)CNC(=O)C(C)N)C(=O)C(=C(C5=O)C)OC)C(=C1OC)O
InChI InChI=1S/C28H36N4O6/c1-12-7-15-8-16-11-32-18(22(31(16)4)20(15)24(34)26(12)37-5)9-17-21(19(32)10-30-28(36)14(3)29)25(35)27(38-6)13(2)23(17)33/h7,14,16,18-19,22,34H,8-11,29H2,1-6H3,(H,30,36)/t14-,16+,18-,19-,22+/m0/s1
InChI Key AZDDAJXLYMVMAW-BVFBRMCBSA-N
Appearance Light Yellow Acicular Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor)
Boiling Point 719.1°C at 760 mmHg
Melting Point >300°C
Density 1.36 g/cm3
1. Activity of safracins A and B, heterocyclic quinone antibiotics, on experimental tumors in mice
T Okumoto, M Kawana, I Nakamura, Y Ikeda, K Isagai J Antibiot (Tokyo). 1985 Jun;38(6):767-71. doi: 10.7164/antibiotics.38.767.
Safracins A and B, new antibiotics produced by Pseudomonas fluorescens A2-2, were tested for antitumor activity against mouse tumors. Structurally, these antibiotics belong to the saframycin family of antibiotics, and safracin B is 21-hydroxysafracin A. They showed antitumor activity against L1210 and P388 leukemias and B16 melanoma. The toxic and effective doses of safracin B were much lower than those of safracin A. Safracin B also prolonged the life span of tumor-bearing mice to a greater extent than safracin A. These results indicate that the alpha-carbinolamine structure plays an important role in the antitumor action of this type of antibiotic. Both safracins were, however, ineffective when their administration route differed from that used for inoculating tumor cells.
2. Safracins, new antitumor antibiotics. II. Physicochemical properties and chemical structures
Y Ikeda, H Matsuki, T Ogawa, T Munakata J Antibiot (Tokyo). 1983 Oct;36(10):1284-9. doi: 10.7164/antibiotics.36.1284.
The chemical structures of safracins A and B are proposed to be 1 and 2 respectively on the basis of their physiocochemical properties and spectrometric studies.
3. Safracins, new antitumor antibiotics. III. Biological activity
Y Ikeda, Y Shimada, K Honjo, T Okumoto, T Munakata J Antibiot (Tokyo). 1983 Oct;36(10):1290-4. doi: 10.7164/antibiotics.36.1290.
Safracins A and B have antibacterial activity against Gram-positive and Gram-negative bacteria in vitro but no therapeutic activity in mice infected with Staphylococcus aureus. Safracins A and B induce abnormal morphological changes in Echerichia coli cells. Tests with transplantable mice tumors demonstrate that safracins A and B inhibit the growth of P388 leukemia and IMC carcinoma.
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