Kigamicin C
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| Category | Antibiotics |
| Catalog number | BBF-01893 |
| CAS | 680571-51-1 |
| Molecular Weight | 809.81 |
| Molecular Formula | C41H47NO16 |
| Purity | >98% by HPLC |
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Description
Selectively kills PANC-1 cells (a pancreatic cell line) at concentrations 100 times lower under nutrient starved conditions than in normal conditions; active in vivo against a human pancreatic cancer xenograft model; also inhibits the growth of gram positive bacteria including MRSA, but is not active against gram negative bacteria.
Specification
| Synonyms | (1S,3R,4S,8aR,11aR)-3-[[(2S,5S,6R)-5-[(2,6-dideoxy-3-O-methyl-b-D-arabinohexopyranosyl)oxy]tetrahydro-6-methyl-2H-pyran-2-yl]oxy]-1,2,3,4,8a,9,11,11a,13,14-decahydro-1,4,17,18-tetrahydroxy-11a-methyl-oxazolo[3,2-b]xantheno[4',3',2':4,5][1,3]benzodioxino[7,6-g]isoquinoline-16,19-dione |
| Storage | -20°C |
| IUPAC Name | (6S,8R,9S,17R,23R)-2,6,9,30-tetrahydroxy-8-[(2S,5S,6R)-5-[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-23-methyl-11,14,16,24-tetraoxa-27-azaoctacyclo[15.14.1.03,12.05,10.013,32.019,31.021,29.023,27]dotriaconta-1(32),2,5(10),12,19,21(29),30-heptaene-4,28-dione |
| Canonical SMILES | CC1C(CCC(O1)OC2CC(C3=C(C2O)OC4=C5C6=C(C7=C(C8=C(CC9(N(C8=O)CCO9)C)C=C7CC6OCO5)O)C(=C4C3=O)O)O)OC1CC(C(C(O1)C)O)OC |
| InChI | InChI=1S/C41H47NO16/c1-15-20(56-25-12-22(50-4)32(44)16(2)55-25)5-6-24(54-15)57-23-11-19(43)28-35(47)31-36(48)30-26-17(9-18-13-41(3)42(7-8-53-41)40(49)27(18)34(26)46)10-21-29(30)38(52-14-51-21)39(31)58-37(28)33(23)45/h9,15-16,19-25,32-33,43-46,48H,5-8,10-14H2,1-4H3/t15-,16-,19+,20+,21-,22-,23-,24+,25+,32-,33+,41-/m1/s1 |
| InChI Key | JXSADZFORZMJRI-KUPVXKSBSA-N |
| Source | Amycolatopsis sp. |
Properties
| Appearance | Pale yellow powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 210-212°C |
| Solubility | Soluble in ethanol, methanol, DMSO, and DMF |
Reference Reading
1. Tetrahydroxanthones by sequential Pd-catalyzed C-O and C-C bond construction and use in the identification of the "antiausterity" pharmacophore of the kigamicins
Penelope A Turner, Michael Shipman, Ellanna M Griffin, Jacqueline L Whatmore Org Lett . 2011 Mar 4;13(5):1056-9. doi: 10.1021/ol103103n.
Readily available C-acylated cycloalkanones undergo efficient Pd catalyzed ring closure/cross-coupling providing 7-substituted tetrahydroxanthones in a single operation. One of the synthesized derivatives (depicted) is shown to selectively kill pancreatic cancer (PANC-1) cells under conditions of nutrient deprivation indicating that the tetrahydroxanthone is responsible, in part, for the "antiausterity" effects of the naturally occurring kigamicins.
2. Kigamicins, novel antitumor antibiotics. I. Taxonomy, isolation, physico-chemical properties and biological activities
Michiyo Ohsono, Tomio Takeuchi, Jie Lu, Yoshiko Honma, Masa Hamada, Hiroyasu Esumi, Setsuko Kunimoto, Yohko Yamazaki, Masaaki Ishizuka, Naoko Kinoshita J Antibiot (Tokyo) . 2003 Dec;56(12):1004-11. doi: 10.7164/antibiotics.56.1004.
Novel antibiotics named kigamicin A, B, C, D, and E were discovered from the culture broth of Amycolatopsis sp. ML630-mF1 by their selective killing activity against PANC-1 cells only under a nutrient starved condition. Under a condition of nutrient starvation, kigamicins A, B, C, and D inhibited PANC-1 cell survival at 100 times lower concentration than in normal culture. Kigamicins showed antimicrobial activity against Gram-positive bacteria including methicillin resistant Staphylococcus aureus (MRSA). Kigamicin D inhibited the growth of various mouse tumor cell lines at IC50 of about 1 microg/ml.
3. Absolute configuration of kigamicins A, C and D
Tetsuya Someno, Hiroshi Naganawa, Daishiro Ikeda, Setsuko Kunimoto, Hikaru Nakamura J Antibiot (Tokyo) . 2005 Jan;58(1):56-60. doi: 10.1038/ja.2005.6.
The stereochemistry of kigamicins A (1), C (2) and D (3) were elucidated by a combination of X-ray crystallographic analysis and degradation studies. The absolute structures of kigamicins thus determined were depicted as shown in Fig. 2.
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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 ╳
