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MedKoo Cat#: 341288 | Name: Chartreusin

Description:

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

Chartreusin is an antibiotic with anticancer activity.

Chemical Structure

Chartreusin
Chartreusin
CAS#6377-18-0

Theoretical Analysis

MedKoo Cat#: 341288

Name: Chartreusin

CAS#: 6377-18-0

Chemical Formula: C32H32O14

Exact Mass: 640.1792

Molecular Weight: 640.59

Elemental Analysis: C, 60.00; H, 5.04; O, 34.97

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
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

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
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. 3: Knop K, Stumpf S, Schubert US. Drugs as matrix to detect their own drug delivery system of PEG-b-PCL block copolymers in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2013 Oct 15;27(19):2201-12. doi: 10.1002/rcm.6663. PubMed PMID: 23996394. 4: Kirubakaran P, Kothapalli R, Singh KhD, Nagamani S, Arjunan S, Muthusamy K. In silico studies on marine actinomycetes as potential inhibitors for Glioblastoma multiforme. Bioinformation. 2011 Apr 22;6(3):100-6. PubMed PMID: 21584184; PubMed Central PMCID: PMC3089882. 5: Xu Z, Jakobi K, Welzel K, Hertweck C. Biosynthesis of the antitumor agent chartreusin involves the oxidative rearrangement of an anthracyclic polyketide. Chem Biol. 2005 May;12(5):579-88. PubMed PMID: 15911378. 6: Weissman K. A new origin for chartreusin. Chem Biol. 2005 May;12(5):512-4. PubMed PMID: 15911371. 7: Barceló F, Portugal J. Elsamicin A binding to DNA. A comparative thermodynamic characterization. FEBS Lett. 2004 Oct 8;576(1-2):68-72. PubMed PMID: 15474012. 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.