Chartreusin

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

Hodoodo CAT#: H341288

CAS#: 6377-18-0

Description: Chartreusin is an antibiotic with anticancer activity.


Chemical Structure

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Chartreusin
CAS# 6377-18-0

Theoretical Analysis

Hodoodo Cat#: H341288
Name: Chartreusin
CAS#: 6377-18-0
Chemical Formula: C32H32O14
Exact Mass: 640.18
Molecular Weight: 640.594
Elemental Analysis: C, 60.00; H, 5.04; O, 34.97

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Chartreusin; NSC 5159; NSC-5159; NSC5159;

IUPAC/Chemical Name: Benzo(h)(1)benzopyrano(5,4,3-cde)(1)benzopyran-5,12-dione, 10-((6-deoxy-2-O-(6-deoxy-3-O-methyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyl)oxy)-6-hydroxy-1-methyl- (9CI)

InChi Key: PONPPNYZKHNPKZ-RYBWXQSLSA-N

InChi Code: InChI=1S/C32H32O14/c1-10-8-9-15-18-16(10)29(38)45-26-17-13(23(35)20(19(18)26)30(39)43-15)6-5-7-14(17)44-32-28(24(36)21(33)11(2)42-32)46-31-25(37)27(40-4)22(34)12(3)41-31/h5-9,11-12,21-22,24-25,27-28,31-37H,1-4H3/t11-,12-,21+,22+,24+,25-,27+,28-,31-,32+/m1/s1

SMILES Code: O=C1OC2=C(C3=C1C(O)=C4C(C(O[C@H]5[C@@H]([C@H]([C@H]([C@@H](C)O5)O)O)O[C@@H]6[C@@H]([C@H]([C@H]([C@@H](C)O6)O)OC)O)=CC=C4)=C3O7)C(C7=O)=C(C)C=C2

Appearance: Solid powder

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: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 640.59 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Ueberschaar N, Meyer F, Dahse HM, Hertweck C. Bipiperidine conjugates as soluble sugar surrogates in DNA-intercalating antiproliferative polyketides. Chem Commun (Camb). 2016 Apr 7;52(27):4894-7. doi: 10.1039/c6cc00890a. Epub 2016 Mar 14. PubMed PMID: 26974406.

2: Ueberschaar N, Xu Z, Scherlach K, Metsä-Ketelä M, Bretschneider T, Dahse HM, Görls H, Hertweck C. Synthetic remodeling of the chartreusin pathway to tune antiproliferative and antibacterial activities. J Am Chem Soc. 2013 Nov 20;135(46):17408-16. doi: 10.1021/ja4080024. Epub 2013 Nov 6. PubMed PMID: 24143864.

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6: Weissman K. A new origin for chartreusin. Chem Biol. 2005 May;12(5):512-4. PubMed PMID: 15911371.

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8: Portugal J. Chartreusin, elsamicin A and related anti-cancer antibiotics. Curr Med Chem Anticancer Agents. 2003 Nov;3(6):411-20. Review. PubMed PMID: 14529449.

9: Kamitori S, Tanaka M, Akita Y, Yamamoto K. Crystal structure of chartreusin derivative A132. Carbohydr Res. 2003 Jul 4;338(14):1523-5. PubMed PMID: 12829398.

10: Barceló F, Capó D, Portugal J. Thermodynamic characterization of the multivalent binding of chartreusin to DNA. Nucleic Acids Res. 2002 Oct 15;30(20):4567-73. PubMed PMID: 12384604; PubMed Central PMCID: PMC137122.

11: Asai G, Yamamoto N, Toi M, Shin E, Nishiyama K, Sekine T, Nomura Y, Takashima S, Kimura M, Tominaga T. Pharmacokinetic and pharmacodynamic study of IST-622, a novel synthetic derivative of chartreusin, by oral administration in a phase II study of patients with breast cancer. Cancer Chemother Pharmacol. 2002 Jun;49(6):468-72. Epub 2002 Apr 9. PubMed PMID: 12107551.

12: Shen LL. DNA-unwinding test using eukaryotic DNA topoisomerase I. Methods Mol Biol. 2001;95:149-60. PubMed PMID: 11089228.

13: Uchida H, Nakakita Y, Enoki N, Abe N, Nakamura T, Munekata M. Chrymutasins: novel-aglycone antitumor antibiotics from a mutant of Streptomyces chartreusis. II. Characterization and structural elucidation. J Antibiot (Tokyo). 1994 Jun;47(6):655-67. PubMed PMID: 8040070.

14: Uchida H, Nakakita Y, Enoki N, Abe N, Nakamura T, Munekata M. Chrymutasins: novel-aglycone antitumor antibiotics from a mutant of Streptomyces chartreusis. I. Taxonomy, mutation, fermentation, isolation and biological activities. J Antibiot (Tokyo). 1994 Jun;47(6):648-54. PubMed PMID: 8040069.

15: Tashiro T, Kon K, Yamamoto M, Yamada N, Tsuruo T, Tsukagoshi S. Antitumor effects of IST-622, a novel synthetic derivative of chartreusin, against murine and human tumor lines following oral administration. Cancer Chemother Pharmacol. 1994;34(4):287-92. PubMed PMID: 8033294.

16: Klein I, Welink J, van der Vijgh WJ. Determination of Elsamitrucin (BMY-28090) in plasma and urine by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1993 Dec 22;622(2):249-53. PubMed PMID: 8150873.

17: Uchida H, Nakakita Y, Enoki N, Abe N, Nakamura T, Munekata M. A novel compound related to chartreusin from a mutant of Streptomyces chartreusis. J Antibiot (Tokyo). 1993 Oct;46(10):1611-5. PubMed PMID: 8244891.

18: Furue H. [Topoisomerase inhibitors developing in Japan]. Gan To Kagaku Ryoho. 1993 Jan;20(1):42-9. Review. Japanese. PubMed PMID: 8422186.

19: Lorico A, Long BH. Biochemical characterisation of elsamicin and other coumarin-related antitumour agents as potent inhibitors of human topoisomerase II. Eur J Cancer. 1993;29A(14):1985-91. PubMed PMID: 8280493.

20: Silvestrini R, Sanfilippo O, Zaffaroni N, De Marco C, Catania S. Activity of a chartreusin analog, elsamicin A, on breast cancer cells. Anticancer Drugs. 1992 Dec;3(6):677-81. PubMed PMID: 1288737.