Argifin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00075 |
| CAS | 243975-37-3 |
| Molecular Weight | 675.69 |
| Molecular Formula | C29H41N9O10 |
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Description
Argifin is a sub-nanomolar chitinase inhibitor produced by soil microorganisms, with IC50s of 0.025 μM, 6.4 μM , 1.1 μM and 4.5 μM for SmChiA (Serratia marcescens chitinaese A), SmChiB, Aspergillus fumigatus chitinase B1 and human chitotriosidase, respectively.
Specification
| IUPAC Name | (2R,5S,8S,11S,15S)-5-[3-[[amino-(methylcarbamoylamino)methylidene]amino]propyl]-8-benzyl-2,7-dimethyl-3,6,9,13,17-pentaoxo-1,4,7,10,14-pentazacycloheptadecane-11,15-dicarboxylic acid |
| Canonical SMILES | CC1C(=O)NC(C(=O)N(C(C(=O)NC(CC(=O)NC(CC(=O)N1)C(=O)O)C(=O)O)CC2=CC=CC=C2)C)CCCN=C(N)NC(=O)NC |
| InChI | InChI=1S/C29H41N9O10/c1-15-23(41)35-17(10-7-11-32-28(30)37-29(48)31-2)25(43)38(3)20(12-16-8-5-4-6-9-16)24(42)36-19(27(46)47)14-22(40)34-18(26(44)45)13-21(39)33-15/h4-6,8-9,15,17-20H,7,10-14H2,1-3H3,(H,33,39)(H,34,40)(H,35,41)(H,36,42)(H,44,45)(H,46,47)(H4,30,31,32,37,48)/t15-,17+,18+,19+,20+/m1/s1 |
| InChI Key | UHBHXSDKGLPPGO-HTDHLNIYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 290°C (dec.) |
Reference Reading
1. An efficient synthesis of argifin: a natural product chitinase inhibitor with chemotherapeutic potential
Daan M F van Aalten, Mark J Dixon, Ian M Eggleston, Ole A Andersen Bioorg Med Chem Lett . 2005 Nov 1;15(21):4717-21. doi: 10.1016/j.bmcl.2005.07.068.
The first synthesis of the cyclopentapeptide family 18 chitinase inhibitor argifin has been achieved by a combination of solid phase and solution chemistry. Synthetic argifin is a nanomolar inhibitor of chitinase B1 from Aspergillus fumigatus and the high-resolution X-ray structure of the synthesized material in complex with the same enzyme is identical to that previously obtained for the natural product.
2. Argifin, a new chitinase inhibitor, produced by Gliocladium sp. FTD-0668. I. Taxonomy, fermentation, and biological activities
N Arai, A Turberg, M Namikoshi, R Masuma, H Kölbl, S Omura, Y Yamaguchi, Y Iwai, K Shiomi J Antibiot (Tokyo) . 2000 Jun;53(6):603-8. doi: 10.7164/antibiotics.53.603.
A new chitinase inhibitor, named argifin, was isolated from the cultured broth of a fungal strain FTD-0668. The strain was identified as Gliocladium sp. from morphological characteristics. The IC50 value of argifin against Lucilia cuprina chitinase was 3.7 microM. Argifin arrested the moult of cockroach larvae upon injection into the ventral abdominal part.
3. Solid-phase synthesis of cyclic peptide chitinase inhibitors: SAR of the argifin scaffold
Amit Nathubhai, Ole A Andersen, Daan M F van Aalten, Ian M Eggleston, Mark J Dixon Org Biomol Chem . 2009 Jan 21;7(2):259-68. doi: 10.1039/b815077j.
A new, highly efficient, all-solid-phase synthesis of argifin, a natural product cyclic pentapeptide chitinase inhibitor, is reported. The synthesis features attachment of an orthogonally protected Asp residue to the solid support and assembly of the linear peptide chain by Fmoc SPPS prior to cyclisation and side-chain manipulation on-resin. Introduction of the key N-methyl carbamoyl-substituted Arg side chain is achieved via derivatisation of a selectively protected Orn residue, prior to cleavage from the resin and side-chain deprotection. A severe aspartimide side-reaction observed upon final deprotection is circumvented by the use of a novel aqueous acidolysis procedure. The flexibility of the synthesis is demonstrated by the preparation of a series of argifin analogues designed from the X-ray structure of the natural product in complex with a representative family 18 chitinase.
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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 ╳
