Vicenistatin | CAS#150999-05-6 | endosome vacuolating compound

MedKoo Cat#: 145424 | Name: Vicenistatin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Vicenistatin is an early endosome vacuolating compound. VICENISTATIN is a novel compound that induces the formation of vacuole-like structures by activating Rab5-PAS pathway and increasing membrane fluidity. VICENISTATIN is an antitumor antibiotic. VICENISTATIN exhibits antitumor activity against human colon carcinoma Co-3 in the xenograft model.

Chemical Structure

Vicenistatin

CAS#150999-05-6

Theoretical Analysis

MedKoo Cat#: 145424

Name: Vicenistatin

CAS#: 150999-05-6

Chemical Formula: C30H48N2O4

Exact Mass: 500.3614

Molecular Weight: 500.72

Elemental Analysis: C, 71.96; H, 9.66; N, 5.59; O, 12.78

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Vicenistatin; NSC-641691; Vicenistatine;

IUPAC/Chemical Name

(3E,5E,7S,8S,10E,13E,15E,19S)-8-(((2R,4S,5S,6R)-4-hydroxy-6-methyl-5-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-7,11,13,19-tetramethylazacycloicosa-3,5,10,13,15-pentaen-2-one

InChi Key

FINGADBUNZWVLV-KVAOKYIVSA-N

InChi Code

1S/C30H48N2O4/c1-21-12-8-7-9-13-23(3)20-32-28(34)15-11-10-14-24(4)27(17-16-22(2)18-21)36-29-19-26(33)30(31-6)25(5)35-29/h7-8,10-12,14-16,23-27,29-31,33H,9,13,17-20H2,1-6H3,(H,32,34)/b8-7+,14-10+,15-11+,21-12+,22-16+/t23-,24-,25+,26-,27-,29-,30+/m0/s1

SMILES Code

CN[C@H]1[C@@H](O)C[C@H](O[C@H]2C\C=C(C)\C\C(C)=C\C=C\CC[C@H](C)CNC(=O)\C=C\C=C\[C@@H]2C)O[C@@H]1C

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 500.72 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Nishiyama Y, Ohmichi T, Kazami S, Iwasaki H, Mano K, Nagumo Y, Kudo F, Ichikawa S, Iwabuchi Y, Kanoh N, Eguchi T, Osada H, Usui T. Vicenistatin induces early endosome-derived vacuole formation in mammalian cells. Biosci Biotechnol Biochem. 2016 May;80(5):902-10. doi: 10.1080/09168451.2015.1132152. Epub 2016 Feb 1. PMID: 27104762. 2: Miyanaga A, Nagata K, Nakajima J, Chisuga T, Kudo F, Eguchi T. Structural Basis of Amide-Forming Adenylation Enzyme VinM in Vicenistatin Biosynthesis. ACS Chem Biol. 2023 Nov 17;18(11):2343-2348. doi: 10.1021/acschembio.3c00517. Epub 2023 Oct 23. PMID: 37870408. 3: Shindo K, Kamishohara M, Odagawa A, Matsuoka M, Kawai H. Vicenistatin, a novel 20-membered macrocyclic lactam antitumor antibiotic. J Antibiot (Tokyo). 1993 Jul;46(7):1076-81. doi: 10.7164/antibiotics.46.1076. PMID: 8360102. 4: Liang Z, Li J, Ling C, Xu R, Yi X, Ju J, Li Q. Characterization of the Aminosugar Biosynthetic and Regulatory Genes of Vicenistatin in Monodonata labio-Associated Streptomyces parvus SCSIO Mla-L010. J Nat Prod. 2022 Jan 28;85(1):256-263. doi: 10.1021/acs.jnatprod.1c01044. Epub 2022 Jan 18. PMID: 35042332. 5: Chisuga T, Miyanaga A, Eguchi T. Protein-Protein Recognition Involved in the Intermodular Transacylation Reaction in Modular Polyketide Synthase in the Biosynthesis of Vicenistatin. Chembiochem. 2022 Jul 19;23(14):e202200200. doi: 10.1002/cbic.202200200. Epub 2022 May 16. PMID: 35501288; PMCID: PMC9401018. 6: Li J, Yang Z, Shi C, Wu X, Zhou L, Liang Y, Li Q, Ju J. Semi-synthesis and structure-activity relationship study yield antibacterial vicenistatin derivatives with low cytotoxicity. J Antibiot (Tokyo). 2024 Apr;77(4):221-227. doi: 10.1038/s41429-023-00701-3. Epub 2024 Jan 16. PMID: 38228780. 7: Miyanaga A, Kawada K, Chisuga T, Kudo F, Eguchi T. Structural Basis of Transient Interactions of Acyltransferase VinK with the Loading Acyl Carrier Protein of the Vicenistatin Modular Polyketide Synthase. Biochemistry. 2023 Jan 3;62(1):17-21. doi: 10.1021/acs.biochem.2c00645. Epub 2022 Dec 13. PMID: 36512613. 8: Miyanaga A, Iwasawa S, Shinohara Y, Kudo F, Eguchi T. Structure-based analysis of the molecular interactions between acyltransferase and acyl carrier protein in vicenistatin biosynthesis. Proc Natl Acad Sci U S A. 2016 Feb 16;113(7):1802-7. doi: 10.1073/pnas.1520042113. Epub 2016 Feb 1. PMID: 26831085; PMCID: PMC4763789. 9: Ogasawara Y, Katayama K, Minami A, Otsuka M, Eguchi T, Kakinuma K. Cloning, sequencing, and functional analysis of the biosynthetic gene cluster of macrolactam antibiotic vicenistatin in Streptomyces halstedii. Chem Biol. 2004 Jan;11(1):79-86. doi: 10.1016/j.chembiol.2003.12.010. PMID: 15112997. 10: Fukuda H, Nishiyama Y, Nakamura S, Ohno Y, Eguchi T, Iwabuchi Y, Usui T, Kanoh N. Synthesis and structure-activity relationship of vicenistatin, a cytotoxic 20-membered macrolactam glycoside. Chem Asian J. 2012 Dec;7(12):2872-81. doi: 10.1002/asia.201200615. Epub 2012 Sep 27. PMID: 23015368. 11: Matsushima Y, Nakayama T, Fujita M, Bhandari R, Eguchi T, Shindo K, Kakinuma K. Isolation and structure elucidation of vicenistatin M, and importance of the vicenisamine aminosugar for exerting cytotoxicity of vicenistatin. J Antibiot (Tokyo). 2001 Mar;54(3):211-9. doi: 10.7164/antibiotics.54.211. PMID: 11372778. 12: Ogasawara Y, Kakinuma K, Eguchi T. Involvement of glutamate mutase in the biosynthesis of the unique starter unit of the macrolactam polyketide antibiotic vicenistatin. J Antibiot (Tokyo). 2005 Jul;58(7):468-72. doi: 10.1038/ja.2005.62. PMID: 16161486. 13: Miyanaga A, Kudo F, Eguchi T. Mechanisms of β-amino acid incorporation in polyketide macrolactam biosynthesis. Curr Opin Chem Biol. 2016 Dec;35:58-64. doi: 10.1016/j.cbpa.2016.08.030. Epub 2016 Sep 10. PMID: 27619002. 14: Miyanaga A, Kudo F, Eguchi T. Protein-protein interactions in polyketide synthase-nonribosomal peptide synthetase hybrid assembly lines. Nat Prod Rep. 2018 Nov 14;35(11):1185-1209. doi: 10.1039/c8np00022k. PMID: 30074030. 15: Matsushima Y, Itoh H, Eguchi T, Kakinuma K. Enantioselective and convergent synthesis of the 20-membered lactam aglycon of vicenistatin antitumor antibiotic. J Antibiot (Tokyo). 1998 Jul;51(7):688-91. doi: 10.7164/antibiotics.51.688. PMID: 9727397. 16: Minami A, Eguchi T. Substrate flexibility of vicenisaminyltransferase VinC involved in the biosynthesis of vicenistatin. J Am Chem Soc. 2007 Apr 25;129(16):5102-7. doi: 10.1021/ja0685250. Epub 2007 Mar 28. PMID: 17388594. 17: Kudo F. Biosynthesis of macrolactam antibiotics with β-amino acid polyketide starter units. J Antibiot (Tokyo). 2024 May 30. doi: 10.1038/s41429-024-00742-2. Epub ahead of print. PMID: 38816450. 18: Miyanaga A, Ouchi R, Kudo F, Eguchi T. Complex structure of the acyltransferase VinK and the carrier protein VinL with a pantetheine cross- linking probe. Acta Crystallogr F Struct Biol Commun. 2021 Sep 1;77(Pt 9):294-302. doi: 10.1107/S2053230X21008761. Epub 2021 Aug 26. PMID: 34473106; PMCID: PMC8411932. 19: Williams GJ, Thorson JS. Natural product glycosyltransferases: properties and applications. Adv Enzymol Relat Areas Mol Biol. 2009;76:55-119. doi: 10.1002/9780470392881.ch2. PMID: 18990828. 20: Shinohara Y, Kudo F, Eguchi T. A natural protecting group strategy to carry an amino acid starter unit in the biosynthesis of macrolactam polyketide antibiotics. J Am Chem Soc. 2011 Nov 16;133(45):18134-7. doi: 10.1021/ja208927r. Epub 2011 Oct 25. PMID: 22010945.