Hygrolidin - CAS# 83329-73-1

Hygrolidin is a 16-membered macrolide antibiotic produced by Streptomyces hygroscopicus D-1166. Hygrolidin has anti-fungus activity against Valsa ceratosperma. Hygrolidin induces p21 expression and abrogates cell cycle progression at G1 and S phases. Hygrolidin has antitumor activity.

Product information

CAS Number: 83329-73-1

Molecular Weight: 690.86

Formula: C38H58O11

Chemical Name: (2E)-4-{[(2R, 4R, 5S, 6R)-6-ethyl-2-hydroxy-2-[(2S, 3R, 4S)-3-hydroxy-4-[(2R, 3S, 9S, 10S, 11R)-10-hydroxy-3-methoxy-7, 9, 11, 13, 15-pentamethyl-16-oxo-1-oxacyclohexadeca-4, 6, 12, 14-tetraen-2-yl]pentan-2-yl]-5-methyloxan-4-yl]oxy}-4-oxobut-2-enoic acid

Smiles: CO[C@H]1C=CC=C(C)C[C@H](C)[C@H](O)[C@H](C)C=C(C)C=C(C)C(=O)O[C@@H]1[C@@H](C)[C@@H](O)[C@H](C)[C@@]1(O)C[C@@H](OC(=O)/C=C/C(O)=O)[C@@H](C)[C@@H](CC)O1 |c:5,15,18,t:3|

InChiKey: UGIOXKVQFJIRMZ-HRNPMOGOSA-N

InChi: InChI=1S/C38H58O11/c1-11-29-26(7)31(47-33(41)16-15-32(39)40)20-38(45,49-29)28(9)35(43)27(8)36-30(46-10)14-12-13-21(2)17-23(4)34(42)24(5)18-22(3)19-25(6)37(44)48-36/h12-16,18-19,23-24,26-31,34-36,42-43,45H,11,17,20H2,1-10H3,(H,39,40)/b14-12-,16-15+,21-13-,22-18-,25-19-/t23-,24+,26-,27-,28-,29+,30-,31+,34-,35+,36+,38+/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Hygrolidin (0.1, 1 μg/ml; for 24 h) increases both G1 and S phase populations and decreases M phase population. Hygrolidin (0.1, 1, 10 μg/ml; for 24 h) decreases the amounts of cdk4, cyclin D, cyclin B and increases the amounts of cyclin E and p21. Hygrolidin-induced p21 preferentially associates with cyclin A-cdk2 complex and inhibits it. Hygrolidin (0.1, 1 μg/ml; for 24 h) selectively induces p21 in DLD-1 cells at mRNA level, but not in WI-38 fibroblasts. Hygrolidin, for 3 days, inhibits growth of various cell lines including DLD-1 colon cancer, LNCaP prostate cancer, K562 leukemia cells, LNCaP prostate cancer, EL-4 lymphoma (IC50s = 1.0-33 ng/ml, respectively). Hygrolidin shows growth inhibition on Trypanosoma cruzi (IC50=1.1 nM), Trypanosoma brucei brucei (IC50=77 nM), and Leishmania donovani (IC50=72.5 nM).

References:

1. Manabu Kawada, et al. Hygrolidin induces p21 expression and abrogates cell cycle progression at G1 and S phases. Biochem Biophys Res Commun. 2002 Oct 18;298(1):178-83.
2. H Seto, et al. The isolation and structures of hygrolidin amide and defumarylhygrolidin. J Antibiot (Tokyo). 1984 May;37(5):610-3.
3. F Annang, et al. High-throughput screening platform for natural product-based drug discovery against 3 neglected tropical diseases: human African trypanosomiasis, leishmaniasis, and Chagas disease. J Biomol Screen. 2015 Jan;20(1):82-91.

Products are for research use only. Not for human use.