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Hygrolidin - CAS 83329-73-1 Catalog number: BADC-00840
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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.
Category
ADCs Cytotoxin
Product Name
Hygrolidin
CAS
83329-73-1
Catalog Number
BADC-00840
Molecular Formula
C38H58O11
Molecular Weight
690.86
Target
Ordering Information
| Catalog Number | Size | Price | Quantity |
|---|---|---|---|
| BADC-00840 | -- | $-- |
Description
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.
Synonyms
(E)-4-[(2R,4R,5S,6R)-6-ethyl-2-hydroxy-2-[(2S,3R,4S)-3-hydroxy-4-[(2R,3S,4E,6E,9S,10S,11R,12Z,14Z)-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
IUPAC Name
(E)-4-[(2R,4R,5S,6R)-6-ethyl-2-hydroxy-2-[(2S,3R,4S)-3-hydroxy-4-[(2R,3S,4E,6E,9S,10S,11R,12Z,14Z)-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
Canonical SMILES
CCC1C(C(CC(O1)(C(C)C(C(C)C2C(C=CC=C(CC(C(C(C=C(C=C(C(=O)O2)C)C)C)O)C)C)OC)O)O)OC(=O)C=CC(=O)O)C
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
InChIKey
UGIOXKVQFJIRMZ-VRHCWVDTSA-N
Density
1.2±0.1 g/cm3
Solubility
10 mm in DMSO
Melting Point
105-107°C
LogP
5.05440
PSA
169.05000
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). Cell Cycle Analysis Cell Line: DLD-1 cells Concentration: 0.1, 1 μg/ml Incubation Time: For 24 hours Result: Increased both G1 and S phase populations and decreased M phase population. Western Blot Analysis Cell Line: DLD-1 cells Concentration: 0.1, 1, 10 μg/ml Incubation Time: For 24 hours Result: Decreased the amounts of cdk4, cyclin D, cyclin B and increased the amounts of cyclin E and p21. RT-PCR Cell Line: DLD-1 or WI-38 cells Concentration: 0.1, 1 μg/ml Incubation Time: For 24 hours Result: Selectively induced p21 in DLD-1 cells at mRNA level, but not in WI-38 fibroblasts.
Source
Streptomyces sp.
Appearance
White Powder
Purity
≥97.0%
Shelf Life
≥ 2 years
Shipping
Room temperature, or blue ice upon request.
Storage
Store at -20 °C, keep in dry and avoid sunlight.
Boiling Point
836.2±65.0 °C at 760 mmHg
Form
Solid
1. Development of a concise and diversity-oriented approach for the synthesis of plecomacrolides via the diene-ene RCM
Kui Lu, Mengwei Huang, Jiahua Chen, Zheng Xiang, Yongxiang Liu, Zhen Yang Org Lett . 2006 Mar 16;8(6):1193-6. doi: 10.1021/ol060221v.
[reaction: see text] A concise synthesis of the core structures of plecomacrolide with ring sizes varying from 16 to 19 atoms was achieved for the first time by the diene-ene ring-closing olefin metathesis reaction. This approach should allow access to the structurally diverse analogues of plecomacrolide.
2. PC-766B, a new macrolide antibiotic produced by Nocardia brasiliensis. II. Isolation, physico-chemical properties and structure elucidation
S Nabeshima, A Fukui, S Tanaka, K Moriguchi, M Ikemoto, K Kumagai J Antibiot (Tokyo) . 1993 Jul;46(7):1139-44. doi: 10.7164/antibiotics.46.1139.
A new macrolide antibiotic, PC-766B, was isolated from the cells of Nocardia brasiliensis SC-4710 by acetone extraction, and purified by gel filtration, silica gel chromatography, HPLC and TLC. The structure of PC-766B was determined by NMR spectral analysis to be a new class of the hygrolidin family antibiotics. PC-766B had a 16-membered macrocyclic lactone ring, a 6-membered hemiketal ring and a 2-deoxy-D-rhamnose moiety. DL-alpha-Tocopherol, known as an antioxidant agent, significantly improved the stability of PC-766B and prevented the decomposition of PC-766B during the storage of the antibiotic.
3. Screening for microbial potentiators of neutral lipid degradation in CHO-K1 cells
Elyza Aiman Azizah Nur, Keisuke Kobayashi, Satoshi Ohte, Hiroshi Tomoda, Taichi Ohshiro Drug Discov Ther . 2022 Dec 1. doi: 10.5582/ddt.2022.01087.
A cell-based assay was conducted to screen microbial culture broths for potentiators of neutral lipid degradation in Chinese Hamster Ovary K1 cells. A total of 5,363 microbial cultures from fungi and actinomycetes were screened in this assay. Brefeldin A (1) from fungal cultures was found to promote the degradation of triacylglycerol (TG) with an EC50of 2.6 µM. Beauveriolides I (2), III (3), beauverolides A (4), B (5), and K (6) from fungal cultures showed potentiating effect on cholesteryl ester (CE) degradation with EC50s ranging from 0.02 to 0.13 µM. Among these compounds, 2 and 6 exhibited the strongest activities (EC50, 0.02 µM). From actinomycete cultures, oxohygrolidin (7) (EC50for TG and CE, > 1.7 and 0.8 µM, respectively) and hygrolidin (8) (EC50for TG and CE, 0.08 and 0.004 µM, respectively) promoted degradation of CE more preferably than TG.
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