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MedKoo Cat#: 585343 | Name: Steffimycin

Description:

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

Steffimycin is an anthracycline antibiotic.

Chemical Structure

Steffimycin
Steffimycin
CAS#11033-34-4

Theoretical Analysis

MedKoo Cat#: 585343

Name: Steffimycin

CAS#: 11033-34-4

Chemical Formula: C28H30O13

Exact Mass: 574.1686

Molecular Weight: 574.54

Elemental Analysis: C, 58.54; H, 5.26; O, 36.20

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
Steffimycin; U 20661; U-20,661; U20661; U-20661
IUPAC/Chemical Name
(2S,3S,4R)-4-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy-2,5,7-trihydroxy-3,9-dimethoxy-2-methyl-3,4-dihydrotetracene-1,6,11-trione
InChi Key
HWMJTJZEJBSVCG-GPDBLRFJSA-N
InChi Code
InChI=1S/C28H30O13/c1-9-18(30)22(34)24(38-4)27(40-9)41-23-17-13(25(35)28(2,36)26(23)39-5)8-12-16(21(17)33)20(32)15-11(19(12)31)6-10(37-3)7-14(15)29/h6-9,18,22-24,26-27,29-30,33-34,36H,1-5H3/t9-,18-,22+,23+,24+,26-,27-,28+/m0/s1
SMILES Code
O=C1[C@@](C)(O)[C@@H](OC)[C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2OC)C3=C(O)C4=C(C(C5=CC(OC)=CC(O)=C5C4=O)=O)C=C13
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 574.54 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: Brodasky TF, Mizsak S, Hoffstetter JR. Steffimycin C, a new member of the steffimycin anthracyclines. Isolation and structural characterization. J Antibiot (Tokyo). 1985 Jul;38(7):849-55. PubMed PMID: 3839781. 2: Wang G, Chen J, Zhu H, Rohr J. One-Pot Enzymatic Total Synthesis of Presteffimycinone, an Early Intermediate of the Anthracycline Antibiotic Steffimycin Biosynthesis. Org Lett. 2017 Feb 3;19(3):540-543. doi: 10.1021/acs.orglett.6b03708. Epub 2017 Jan 19. PubMed PMID: 28102686; PubMed Central PMCID: PMC5502540. 3: Gullón S, Olano C, Abdelfattah MS, Braña AF, Rohr J, Méndez C, Salas JA. Isolation, characterization, and heterologous expression of the biosynthesis gene cluster for the antitumor anthracycline steffimycin. Appl Environ Microbiol. 2006 Jun;72(6):4172-83. PubMed PMID: 16751529; PubMed Central PMCID: PMC1489666. 4: Reusser F. Steffimycin B, a DNA binding agent. Biochim Biophys Acta. 1975 Mar 21;383(3):266-73. PubMed PMID: 1090304. 5: Sriram M, Liaw YC, Gao YG, Wang AH. Molecular structure of antitumor drug steffimycin and modelling of its binding to DNA. J Biomol Struct Dyn. 1991 Oct;9(2):251-69. PubMed PMID: 1741962. 6: Olano C, Abdelfattah MS, Gullón S, Braña AF, Rohr J, Méndez C, Salas JA. Glycosylated derivatives of steffimycin: insights into the role of the sugar moieties for the biological activity. Chembiochem. 2008 Mar 3;9(4):624-33. doi: 10.1002/cbic.200700610. PubMed PMID: 18224649. 7: Trenado-Uribe M, Silva-Miranda M, Rivero-Cruz JF, Rodríguez-Peña K, Espitia-Pinzón CI, Rodríguez-Sanoja R, Sánchez S. Antimycobacterial activity of an anthracycline produced by an endophyte isolated from Amphipterygium adstringens. Mol Biol Rep. 2018 Dec;45(6):2563-2570. doi: 10.1007/s11033-018-4424-0. Epub 2018 Oct 11. PubMed PMID: 30311126. 8: Wiley PF, Elrod DW, Slavicek JM, Marshall VP. Microbial conversion of steffimycin and steffimycin B to 10-dihydrosteffimycin and 10-dihydrosteffimycin B. J Antibiot (Tokyo). 1980 Aug;33(8):819-23. PubMed PMID: 7429984. 9: Brodasky TF, Reusser F. Steffimycin B, a new member of the steffimycin family: isolation and characterization. J Antibiot (Tokyo). 1974 Nov;27(11):809-13. PubMed PMID: 4217786. 10: Wiley PF, Elrod DW, Harper DE. Chemical modification of steffimycin B. J Antibiot (Tokyo). 1988 Mar;41(3):343-51. PubMed PMID: 3366692. 11: Reusser F. On the inhibition of ribonucleic synthesis in Bacillus subtilis cells by steffimycin. Biochem Pharmacol. 1968 Sep;17(9):2001-6. PubMed PMID: 4972144. 12: Kunnari T, Tuikkanen J, Hautala A, Hakala J, Ylihonko K, Mäntsälä P. Isolation and characterization of 8-demethoxy steffimycins and generation of 2,8-demethoxy steffimycins in Streptomyces steffisburgensis by the nogalamycin biosynthesis genes. J Antibiot (Tokyo). 1997 Jun;50(6):496-501. PubMed PMID: 9268006. 13: Arora SK. Molecular structure, stereochemistry and interactions of steffimycin B, and DNA binding anthracycline antibiotic. J Biomol Struct Dyn. 1985 Oct;3(2):377-85. PubMed PMID: 3917028. 14: Olano C. Hutchinson's legacy: keeping on polyketide biosynthesis. J Antibiot (Tokyo). 2011 Jan;64(1):51-7. doi: 10.1038/ja.2010.126. Epub 2010 Nov 10. Review. PubMed PMID: 21063423. 15: Kelly RC, Schletter I, Koert JM, MacKellar FA, Wiley PF. Structures of steffimycin and steffimycin B1. J Org Chem. 1977 Oct 28;42(22):3591-6. PubMed PMID: 915579. 16: Rueckert PW, Wiley PF, McGovren JP, Marshall VP. Mammalian and microbial cell-free conversion of anthracycline antibiotics and analogs. J Antibiot (Tokyo). 1979 Feb;32(2):141-7. PubMed PMID: 35508. 17: Reusser F. Effect of steffimycin on cell-free polypeptide synthesis. Biochem Pharmacol. 1969 Feb;18(2):287-94. PubMed PMID: 4888128. 18: Marshall VP, Reisender EA, Reineke LM, Johnson JH, Wiley PF. Reductive microbial conversion of anthracycline antibiotics. Biochemistry. 1976 Sep 21;15(19):4139-45. PubMed PMID: 786368. 19: Suzukake-Tsuchiya K, Moriya Y, Yamazaki K, Hori M, Hosokawa N, Sawa T, Iinuma H, Naganawa H, Imada C, Hamada M. Screening of antibiotics preferentially active against ras oncogene-expressed cells. J Antibiot (Tokyo). 1990 Nov;43(11):1489-96. PubMed PMID: 2272923. 20: Salianov VI, Evdokimov IuM, Berg G. [Changes in the spatial organization of DNA molecules induced by anthracycline antibiotics]. Antibiotiki. 1982 Dec;27(12):38-42. Russian. PubMed PMID: 6962685.