Hibarimicin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00954 |
| CAS | |
| Molecular Weight | 1725.77 |
| Molecular Formula | C85H112O37 |
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Description
Hibarimicin B is a tyrosine kinase inhibitor produced by Microbispora rosea subsp. hibaria. It selectively inhibits the activity of src tyrosine kinase without affecting protein kinase A and C. It also has moderate anti-Gram-positive bacteria activity with a MIC of 0.8-12.56 μg/mL.
Specification
| IUPAC Name | 5-[(2S,5S,6R)-5-[(2S,5R,6R)-5-acetyl-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-15-[9-[(2S,5S,6R)-5-[(2S,5R,6R)-5-acetyl-5-hydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-7-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1,8,10,10a,12-pentahydroxy-3,4-dimethoxy-11-oxo-10-propyl-6a,7,8,9-tetrahydro-6H-tetracen-2-yl]-7-[(4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6,9,12,19-tetrahydroxy-16-methoxy-4-propyl-3-oxapentacyclo[9.8.0.02,8.04,9.013,18]nonadeca-1(11),12,15,18-tetraene-10,14,17-trione |
| Canonical SMILES | CCCC1(C(C(C(C2C1(C(=O)C3=C(C4=C(C=C3C2)C(=C(C(=C4O)C5=C(C(=O)C6=C(C7=C(C(=C6C5=O)O)C(=O)C8(C9C7OC8(C(C(C9OC1CC(C(C(O1)C)O)O)O)OC1CCC(C(O1)C)OC1CCC(C(O1)C)(C(=O)C)O)CCC)O)O)OC)OC)OC)O)O)OC1CC(C(C(O1)C)O)O)O)OC1CCC(C(O1)C)OC1CCC(C(O1)C)(C(=O)C)O)O |
| InChI | InChI=1S/C85H112O37/c1-14-22-82(104)78(120-45-18-16-43(30(3)110-45)116-47-20-24-80(102,34(7)86)36(9)114-47)68(98)71(118-49-28-41(88)60(90)32(5)112-49)40-27-38-26-39-52(62(92)51(38)76(100)84(40,82)105)63(93)56(74(109-13)70(39)107-11)55-64(94)53-54(67(97)73(55)108-12)65(95)57-58(66(53)96)77(101)85(106)59-72(57)122-83(85,23-15-2)79(69(99)75(59)119-50-29-42(89)61(91)33(6)113-50)121-46-19-17-44(31(4)111-46)117-48-21-25-81(103,35(8)87)37(10)115-48/h26,30-33,36-37,40-50,59-61,68-69,71-72,75,78-79,88-93,95-96,98-99,102-106H,14-25,27-29H2,1-13H3/t30-,31-,32+,33+,36-,37-,40?,41-,42-,43+,44+,45+,46+,47-,48-,49+,50?,59?,60+,61+,68?,69?,71?,72?,75?,78?,79?,80+,81+,82?,83?,84?,85?/m1/s1 |
| InChI Key | XGHSXRXEPCUHTN-MWHBNOOJSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | >200°C |
Reference Reading
1. Effects of hibarimicins and hibarimicin-related compounds produced by Microbispora on v-Src kinase activity and growth and differentiation of human myeloid leukemia HL-60 cells
Sung Ig Cho, Hidesuke Fukazawa, Yoshio Honma, Takayuki Kajiura, Hiroshi Hori, Yasuhiro Igarashi, Tamotsu Furumai, Toshikazu Oki, Yoshimasa Uehara J Antibiot (Tokyo). 2002 Mar;55(3):270-8. doi: 10.7164/antibiotics.55.270.
We studied the effects of hibarimicins and hibarimicin-related compounds produced by Microbispora rosea subsp. hibaria [glycosides (hibarimicins A, B, C, D, E, G, H and I) and aglycon (hibarimicinone)] or compounds produced by its mutants [glycosides (HMP-P4 and -Y6), aglycons (HMP-P1 and -Y1) and shunt products (HMP-M1, M2, M3 and -M4)] on v-Src tyrosine kinase and growth and differentiation of human myeloid leukemia HL-60 cells. Among them, hibarimicin B was a strong and the most selective v-Src kinase inhibitor with differentiation inducing activity of HL-60 cells. Hibarimicin E similarly induced HL-60 cell differentiation but had no v-Src kinase inhibitory activity. Hibarimicinone was the most potent v-Src kinase inhibitor, although less selective, and did not induce differentiation of HL-60 cells. Hibarimicin B competitively inhibited ATP binding to the v-Src kinase, but hibarimicinone showed noncompetitive inhibition. These two compounds, however, showed similar mixed types of inhibition against a Src substrate binding to the v-Src kinase. Altogether, these results suggest that signaling molecules other than Src might be more important in the differentiation induction of HL-60 cells.
2. Assignment and stereocontrol of hibarimicin atropoisomers
Ian M Romaine, Jonathan E Hempel, Ganesh Shanmugam, Hiroshi Hori, Yasuhiro Igarashi, Prasad L Polavarapu, Gary A Sulikowski Org Lett. 2011 Sep 2;13(17):4538-41. doi: 10.1021/ol2017005. Epub 2011 Aug 3.
A stereochemical feature of the hibarimicins is a central biaryl (HMP-Y6) or aryl-quinone (hibarimicinone) incorporated as a single atropodiastereomer. Herein, a chiral resolution and deracemization process to access optically enriched biaryls aR-3 and aS-3 is described. From these atropoenantiomers the BCD-EFG ring system of HMP-Y6 is constructed [(+)-aR-7]. Comparison of CD spectra of aR-7 to HMP-Y6 leads to the assignment of HMP-Y6 and hibarimicin B atropoisomers as aR and aS, respectively.
3. Studies toward the total synthesis of angelmicin B (hibarimicin B): synthesis of a model CD-D' arylnaphthoquinone
Sridhar Narayan, William R Roush Org Lett. 2004 Oct 14;6(21):3789-92. doi: 10.1021/ol048436x.
[structure: see text] A synthesis of arylnaphthoquinone 22 corresponding to the CD-D' unit of angelmicin B via the Suzuki coupling of the D' arylboronic acid 15 with the CD bromonaphthoquinone 21 is described. The mild conditions for the Suzuki cross-coupling leading to 22 may prove to be useful for the eventual late-stage coupling of the two highly functionalized halves of angelmicin B.
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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 ╳
