Ravidomycin

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

MedKoo CAT#: 461177

CAS#: 74622-75-6

Description: Ravidomycin is an antitumor antibiotic. It exhibits potent anticancer activities against various cancer cell lines in the presence of visible light.

Chemical Structure

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Ravidomycin
CAS# 74622-75-6
Instruction

Theoretical Analysis

MedKoo Cat#: 461177
Name: Ravidomycin
CAS#: 74622-75-6
Chemical Formula: C31H33NO9
Exact Mass: 563.22
Molecular Weight: 563.600
Elemental Analysis: C, 66.06; H, 5.90; N, 2.49; O, 25.55

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 @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Ravidomycin; AY 25545; AY-25545; AY25545;

IUPAC/Chemical Name: (2R,3R,4R,5R,6S)-4-(dimethylamino)-5-hydroxy-6-(1-hydroxy-10,12-dimethoxy-6-oxo-8-vinyl-6H-dibenzo[c,h]chromen-4-yl)-2-methyltetrahydro-2H-pyran-3-yl acetate

InChi Key: GHLIFBNIGXVDHM-LSXWJJIVSA-N

InChi Code: InChI=1S/C31H33NO9/c1-8-16-11-19-23(21(12-16)37-6)18-13-22(38-7)25-20(34)10-9-17(24(25)29(18)41-31(19)36)30-27(35)26(32(4)5)28(14(2)39-30)40-15(3)33/h8-14,26-28,30,34-35H,1H2,2-7H3/t14-,26-,27-,28+,30+/m1/s1

SMILES Code: Oc1ccc([C@@H]2O[C@H](C)[C@H](OC(C)=O)[C@H](N(C)C)[C@H]2O)c(c1c(OC)cc3c4c(OC)cc(C=C)cc54)c3oc5=O

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: >3 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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 563.60 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: Kharel MK, Nybo SE, Shepherd MD, Rohr J. Cloning and characterization of the ravidomycin and chrysomycin biosynthetic gene clusters. Chembiochem. 2010 Mar 1;11(4):523-32. doi: 10.1002/cbic.200900673. PubMed PMID: 20140934; PubMed Central PMCID: PMC2879346.

2: Sehgal SN, Czerkawski H, Kudelski A, Pandev K, Saucier R, Vézina C. Ravidomycin (AY-25,545), a new antitumor antibiotic. J Antibiot (Tokyo). 1983 Apr;36(4):355-61. PubMed PMID: 6853365.

3: Rakhit S, Eng C, Baker H, Singh K. Chemical modification of ravidomycin and evaluation of biological activities of its derivatives. J Antibiot (Tokyo). 1983 Nov;36(11):1490-4. PubMed PMID: 6654759.

4: Singh K. Studies on the mechanism of action of ravidomycin (AY-25,545). J Antibiot (Tokyo). 1984 Jan;37(1):71-3. PubMed PMID: 6421790.

5: Greenstein M, Monji T, Yeung R, Maiese WM, White RJ. Light-dependent activity of the antitumor antibiotics ravidomycin and desacetylravidomycin. Antimicrob Agents Chemother. 1986 May;29(5):861-6. PubMed PMID: 3729344; PubMed Central PMCID: PMC284168.

6: Kharel MK, Lian H, Rohr J. Characterization of the TDP-D-ravidosamine biosynthetic pathway: one-pot enzymatic synthesis of TDP-D-ravidosamine from thymidine-5-phosphate and glucose-1-phosphate. Org Biomol Chem. 2011 Mar 21;9(6):1799-808. doi: 10.1039/c0ob00854k. Epub 2011 Jan 24. PubMed PMID: 21264378; PubMed Central PMCID: PMC4482361.

7: Yamashita N, Shin-ya K, Furihata K, Hayakawa Y, Seto H. New ravidomycin analogues, FE35A and FE35B, apoptosis inducers produced by Streptomyces rochei. J Antibiot (Tokyo). 1998 Dec;51(12):1105-8. PubMed PMID: 10048570.

8: Kharel MK, Pahari P, Lian H, Rohr J. Enzymatic total synthesis of rabelomycin, an angucycline group antibiotic. Org Lett. 2010 Jun 18;12(12):2814-7. doi: 10.1021/ol1009009. PubMed PMID: 20486694; PubMed Central PMCID: PMC2895501.

9: Kharel MK, Pahari P, Shepherd MD, Tibrewal N, Nybo SE, Shaaban KA, Rohr J. Angucyclines: Biosynthesis, mode-of-action, new natural products, and synthesis. Nat Prod Rep. 2012 Feb;29(2):264-325. doi: 10.1039/c1np00068c. Epub 2011 Dec 21. Review. PubMed PMID: 22186970.

10: Narita T, Matsumoto M, Mogi K, Kukita K, Kawahara R, Nakashima T. Deacetylravidomycin N-oxide, a new antibiotic. Taxonomy and fermentation of the producing organism and isolation, structure and biological properties of the antibiotic. J Antibiot (Tokyo). 1989 Mar;42(3):347-56. PubMed PMID: 2708127.

11: 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.