Hibarimicin D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00956 |
| CAS | 208588-87-8 |
| Molecular Weight | 1741.77 |
| Molecular Formula | C85H112O38 |
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Description
Hibarimicin D 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.
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | >200°C |
Reference Reading
1. Signal transduction inhibitors, hibarimicins A, B, C, D and G produced by Microbispora. II. Structural studies
H Hori, Y Igarashi, T Kajiura, T Furumai, K Higashi, T Ishiyama, M Uramota, Y Uehara, T Oki J Antibiot (Tokyo). 1998 Apr;51(4):402-17. doi: 10.7164/antibiotics.51.402.
The structure of hibarimicins A, B, C, D and G which are inhibitors for tyrosine specific protein kinase are determined using spectroscopic techniques. Hibarimicins described in this report consist of a common aglycon and six deoxyhexoses. The aglycon contains a highly oxidized naphtylnaphthoquinone as a chromophore. Among them, hibarimicin B was identical with angelmicin B.
2. 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.
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 ╳
