Saframycin A

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

MedKoo CAT#: 461698

CAS#: 66082-27-7

Description: Saframycin A is a potent antitumor antibiotic that belongs to the tetrahydroisoquinoline family.

Chemical Structure

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Saframycin A
CAS# 66082-27-7
Instruction

Theoretical Analysis

MedKoo Cat#: 461698
Name: Saframycin A
CAS#: 66082-27-7
Chemical Formula: C29H30N4O8
Exact Mass: 562.21
Molecular Weight: 562.570
Elemental Analysis: C, 61.91; H, 5.38; N, 9.96; O, 22.75

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: Saframycin A; 21-Cyanosaframycin-B;

IUPAC/Chemical Name: N-(((6R,7R,9R,14aS,15S)-7-cyano-2,11-dimethoxy-3,12,16-trimethyl-1,4,10,13-tetraoxo-1,5,6,7,9,10,13,14,14a,15-decahydro-4H-6,15-epiminobenzo[4,5]azocino[1,2-b]isoquinolin-9-yl)methyl)-2-oxopropanamide

InChi Key: JNEGMBHBUAJRSX-NOYKIMNZSA-N

InChi Code: InChI=1S/C29H30N4O8/c1-11-23(35)14-8-17-22-21-15(24(36)12(2)28(41-6)26(21)38)7-16(32(22)4)18(9-30)33(17)19(10-31-29(39)13(3)34)20(14)25(37)27(11)40-5/h16-19,22H,7-8,10H2,1-6H3,(H,31,39)/t16-,17+,18+,19+,22-/m1/s1

SMILES Code: COC1=C(C(C2=C(C1=O)[C@@H](N3[C@H]([C@H]4N([C@@H]([C@@H]3C#N)CC5=C4C(C(OC)=C(C5=O)C)=O)C)C2)CNC(C(C)=O)=O)=O)C

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 562.57 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: Tang MC, Fu CY, Tang GL. Characterization of SfmD as a Heme peroxidase that catalyzes the regioselective hydroxylation of 3-methyltyrosine to 3-hydroxy-5-methyltyrosine in saframycin A biosynthesis. J Biol Chem. 2012 Feb 10;287(7):5112-21. doi: 10.1074/jbc.M111.306316. Epub 2011 Dec 20. PubMed PMID: 22187429; PubMed Central PMCID: PMC3281660.

2: Dong W, Liu W, Yan Z, Liao X, Guan B, Wang N, Liu Z. Asymmetric synthesis and cytotoxicity of (-)-saframycin A analogues. Eur J Med Chem. 2012 Mar;49:239-44. doi: 10.1016/j.ejmech.2012.01.017. Epub 2012 Jan 15. PubMed PMID: 22284268.

3: Dong W, Liu W, Liao X, Guan B, Chen S, Liu Z. Asymmetric total synthesis of (-)-saframycin A from L-tyrosine. J Org Chem. 2011 Jul 1;76(13):5363-8. doi: 10.1021/jo200758r. Epub 2011 Jun 8. PubMed PMID: 21612294.

4: Ishiguro K, Takahashi K, Yazawa K, Sakiyama S, Arai T. Binding of saframycin A, a heterocyclic quinone anti-tumor antibiotic to DNA as revealed by the use of the antibiotic labeled with [14C]tyrosine or [14C]cyanide. J Biol Chem. 1981 Mar 10;256(5):2162-7. PubMed PMID: 7193208.

5: Arai T, Takahashi K, Ishiguro K, Yazawa K. Increased production of saframycin A and isolation of saframycin S. J Antibiot (Tokyo). 1980 Sep;33(9):951-60. PubMed PMID: 7440416.

6: Martinez EJ, Corey EJ. Enantioselective synthesis of saframycin A and evaluation of antitumor activity relative to ecteinascidin/saframycin hybrids. Org Lett. 1999 Jul 15;1(1):75-7. PubMed PMID: 10822537.

7: Arai T, Takahashi K, Nakahara S, Kubo A. The structure of a novel antitumor antibiotic, saframycin A. Experientia. 1980 Sep 15;36(9):1025-7. PubMed PMID: 7418832.

8: Li L, Deng W, Song J, Ding W, Zhao QF, Peng C, Song WW, Tang GL, Liu W. Characterization of the saframycin A gene cluster from Streptomyces lavendulae NRRL 11002 revealing a nonribosomal peptide synthetase system for assembling the unusual tetrapeptidyl skeleton in an iterative manner. J Bacteriol. 2008 Jan;190(1):251-63. Epub 2007 Nov 2. PubMed PMID: 17981978; PubMed Central PMCID: PMC2223732.

9: Mikami Y, Yokoyama K, Tabeta H, Nakagaki K, Arai T. Saframycin S, a new saframycin group antibiotic. J Pharmacobiodyn. 1981 Apr;4(4):282-6. PubMed PMID: 7264873.

10: Xing C, LaPorte JR, Barbay JK, Myers AG. Identification of GAPDH as a protein target of the saframycin antiproliferative agents. Proc Natl Acad Sci U S A. 2004 Apr 20;101(16):5862-6. Epub 2004 Apr 12. PubMed PMID: 15079082; PubMed Central PMCID: PMC395888.

11: Mikami Y, Takahashi K, Yazawa K, Arai T, Namikoshi M, Iwasaki S, Okuda S. Biosynthetic studies on saframycin A, a quinone antitumor antibiotic produced by Streptomyces lavendulae. J Biol Chem. 1985 Jan 10;260(1):344-8. PubMed PMID: 3880741.

12: Takahashi K, Yazawa K, Kishi K, Mikami Y, Arai T, Kubo A. Microbial conversion of saframycin A to 25-dihydrosaframycin A and 21-decyano-25-dihydrosaframycin A (25-dihydrosaframycin B) and their biological activities. J Antibiot (Tokyo). 1982 Feb;35(2):196-202. PubMed PMID: 7076566.

13: Saito N, Harada S, Nishida M, Inouye I, Kubo A. Synthesis of saframycins. X. Transformation of (-)-saframycin A to (-)-saframycin Mx type compound with the structure proposed for saframycin E. Chem Pharm Bull (Tokyo). 1995 May;43(5):777-82. PubMed PMID: 7553964.

14: Myers AG, Lanman BA. A solid-supported, enantioselective synthesis suitable for the rapid preparation of large numbers of diverse structural analogues of (-)-saframycin A. J Am Chem Soc. 2002 Nov 6;124(44):12969-71. PubMed PMID: 12405822.

15: Plowright AT, Schaus SE, Myers AG. Transcriptional response pathways in a yeast strain sensitive to saframycin a and a more potent analog: evidence for a common basis of activity. Chem Biol. 2002 May;9(5):607-18. PubMed PMID: 12031667.

16: Koketsu K, Watanabe K, Suda H, Oguri H, Oikawa H. Reconstruction of the saframycin core scaffold defines dual Pictet-Spengler mechanisms. Nat Chem Biol. 2010 Jun;6(6):408-10. doi: 10.1038/nchembio.365. Epub 2010 May 9. PubMed PMID: 20453862.

17: Hill GC, Remers WA. Computer simulation of the binding of saframycin A to d (GATGCATC)2. J Med Chem. 1991 Jul;34(7):1990-8. PubMed PMID: 2066972.

18: Myers AG, Kung DW. One-step construction of the pentacyclic skeleton of saframycin A from a "Trimer" of alpha-amino aldehydes. Org Lett. 2000 Sep 21;2(19):3019-22. PubMed PMID: 10986097.

19: Spencer JR, Sendzik M, Oeh J, Sabbatini P, Dalrymple SA, Magill C, Kim HM, Zhang P, Squires N, Moss KG, Sukbuntherng J, Graupe D, Eksterowicz J, Young PR, Myers AG, Green MJ. Evaluation of antitumor properties of novel saframycin analogs in vitro and in vivo. Bioorg Med Chem Lett. 2006 Sep 15;16(18):4884-8. Epub 2006 Jul 25. PubMed PMID: 16870445.

20: Yazawa K, Asaoka T, Takahashi K, Mikami Y, Arai T. Bioconversions of saframycin A specific to some genera of actinomycetes. J Antibiot (Tokyo). 1982 Jul;35(7):915-7. PubMed PMID: 7174541.