Lactoquinomycin B

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Lactoquinomycin B
Category Antibiotics
Catalog number BBF-02230
CAS 101342-94-3
Molecular Weight 473.48
Molecular Formula C24H27NO9

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Description

It is produced by the strain of Str. tanashiensis IM 8442T. It's a quinone antibiotic. It has the activity of anti-gram-positive bacteria and some gram-negative bacteria, but the effect of anti-gram-negative bacteria is weak and has no effect on fungi. Lactoquinomycin A has stronger antibacterial activity than Lactoquinomycin B. It inhibits a variety of cell lines including lymphoma L5178Y progenitor, adriamycin resistant, bleomycin-resistant, human leukemia K562, mouse leukemia L-1210 and mouse leukemia P 388 with ID50 (μg/mL) of 0.43, 0.21, 0.19, 0.16, 0.2 and 0.12, respectively.

Specification

Synonyms 3a,11b-Dihydro-7-hydroxy-5-methyl-8-[2,3,6-trideoxy-3-(dimethylamino)-β-D-arabino-hexopyranosyl]-5a,11a-epoxy-5H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11(3H)-trione; 5a,11a-Epoxy-5H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11(3H)-trione, 3a,11b-dihydro-7-hydroxy-5-methyl-8-[2,3,6-trideoxy-3-(dimethylamino)-b-D-arabino-hexopyranosyl]-
IUPAC Name 5-[(2R,4R,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.01,10.03,8.011,15]octadeca-3(8),4,6-triene-2,9,13-trione
Canonical SMILES CC1C(C(CC(O1)C2=C(C3=C(C=C2)C(=O)C45C6C(CC(=O)O6)OC(C4(C3=O)O5)C)O)N(C)C)O
InChI InChI=1S/C24H27NO9/c1-9-18(27)13(25(3)4)7-14(31-9)11-5-6-12-17(19(11)28)21(30)23-10(2)32-15-8-16(26)33-22(15)24(23,34-23)20(12)29/h5-6,9-10,13-15,18,22,27-28H,7-8H2,1-4H3/t9-,10?,13-,14-,15?,18-,22?,23?,24?/m1/s1
InChI Key UKGUMAYTBDAONQ-FZQVSEIZSA-N

Properties

Appearance Light Yellow Crystalline Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Neoplastics (Tumor)
Boiling Point 736.8°C at 760 mmHg
Melting Point 149-152°C (dec.)
Density 1.52 g/cm3
Solubility Soluble in Methanol, Chloroform

Reference Reading

1. Lactoquinomycin B, a novel antibiotic
T Okabe, K Nomoto, N Tanaka J Antibiot (Tokyo). 1986 Jan;39(1):1-5. doi: 10.7164/antibiotics.39.1.
Streptomyces tanashiensis IM8442T was found to produce lactoquinomycin B, a novel antibiotic, together with lactoquinomycin A. Lactoquinomycin B was purified, and the physico-chemical and biological characteristics were studied. Lactoquinomycin B, C24H27NO9, mp 149-152 degrees C (dec), FD-MS m/z 473 (M+), is a basic substance, showing UV lambda MeOHmax (epsilon) 239 (15,100), 287 (3,450) and 369 nm (5,300), and IR nu CHCl3max 1790 (gamma-lactone), and 1700 and 1650 (quinone) cm-1. The structure of lactoquinomycin B was elucidated by 1H NMR and 13C NMR in comparison with those of lactoquinomycin A, indicating that B is a 4a,10a-epoxide derivative of A. Lactoquinomycin B displayed inhibitory activity against bacteria, particularly Gram-positive organisms, and cytotoxicity against human and murine tumor cell lines. LD50 for mice was ca. 40 mg/kg by iv route.
2. Structure revision of medermycin/lactoquinomycin a and of related C-8 glycosylated naphthoquinones
Pierre-Marc Léo, Christophe Morin, Christian Philouze Org Lett. 2002 Aug 8;4(16):2711-4. doi: 10.1021/ol026222e.
[reaction: see text] On the basis of chemical and spectral data, the structure of the medermycin/lactoquinomycin A has been revised, which has also led to the revision of related C-glycosylated naphthoquinone antibiotics such as lactoquinomycin B, menoxymycins A and B, G15-F, and G15-G.

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