Synonym
SF 2575; SF2575; SF-2575
IUPAC/Chemical Name
Benzoic acid, 2-hydroxy-, 3-(aminocarbonyl)-8-(2,6-dideoxy-4-O-(2-methyl-1-oxo-2-butenyl)-beta-D-arabino-hexopyranosyl)-1,4,4a,6,11,11a,12,12a-octahydro-2,5,7-trihydroxy-4a,11-dimethoxy-11-methyl-4,6-dioxo-1-naphthacenyl ester, (1R-(1-alpha,4a-alpha,11-beta,11a-beta,12a-beta))-
InChi Key
MPBVFNYOBQUJEJ-GNOOZHHESA-N
InChi Code
InChI=1S/C40H43NO15/c1-7-16(2)37(50)55-32-17(3)54-25(15-24(32)43)19-12-13-20-26(29(19)44)30(45)27-21(39(20,4)52-5)14-22-33(56-38(51)18-10-8-9-11-23(18)42)31(46)28(36(41)49)35(48)40(22,53-6)34(27)47/h7-13,17,21-22,24-25,32-33,42-44,46-47H,14-15H2,1-6H3,(H2,41,49)/b16-7+/t17-,21-,22-,24-,25-,32-,33+,39-,40+/m1/s1
SMILES Code
O=C(O[C@@H]1C(O)=C(C(N)=O)C([C@@]2(OC)C(O)=C3C(C4=C([C@@](C)(OC)[C@]3([H])C[C@@]21[H])C=CC([C@H]5C[C@H]([C@@H]([C@@H](C)O5)OC(/C(C)=C/C)=O)O)=C4O)=O)=O)C6=CC=CC=C6O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
777.78
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.
| 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: Li L, Wang P, Tang Y. C-glycosylation of anhydrotetracycline scaffold with SsfS6 from the SF2575 biosynthetic pathway. J Antibiot (Tokyo). 2014 Jan;67(1):65-70. doi: 10.1038/ja.2013.88. Epub 2013 Sep 11. PubMed PMID: 24022606.
2: Wang F, Zhou M, Singh S, Yennamalli RM, Bingman CA, Thorson JS, Phillips GN Jr. Crystal structure of SsfS6, the putative C-glycosyltransferase involved in SF2575 biosynthesis. Proteins. 2013 Jul;81(7):1277-82. doi: 10.1002/prot.24289. Epub 2013 Apr 20. PubMed PMID: 23526584; PubMed Central PMCID: PMC3896073.
3: Wang P, Kim W, Pickens LB, Gao X, Tang Y. Heterologous expression and manipulation of three tetracycline biosynthetic pathways. Angew Chem Int Ed Engl. 2012 Oct 29;51(44):11136-40. doi: 10.1002/anie.201205426. Epub 2012 Sep 28. PubMed PMID: 23024027; PubMed Central PMCID: PMC4070387.
4: Pickens LB, Sawaya MR, Rasool H, Pashkov I, Yeates TO, Tang Y. Structural and biochemical characterization of the salicylyl-acyltranferase SsfX3 from a tetracycline biosynthetic pathway. J Biol Chem. 2011 Dec 2;286(48):41539-51. doi: 10.1074/jbc.M111.299859. Epub 2011 Sep 29. PubMed PMID: 21965680; PubMed Central PMCID: PMC3308865.
5: Hatsu M, Sasaki T, Gomi S, Kodama Y, Sezaki M, Inouye S, Kondo S. A new tetracycline antibiotic with antitumor activity. II. The structural elucidation of SF2575. J Antibiot (Tokyo). 1992 Mar;45(3):325-30. PubMed PMID: 1577661.
6: Pickens LB, Kim W, Wang P, Zhou H, Watanabe K, Gomi S, Tang Y. Biochemical analysis of the biosynthetic pathway of an anticancer tetracycline SF2575. J Am Chem Soc. 2009 Dec 9;131(48):17677-89. doi: 10.1021/ja907852c. PubMed PMID: 19908837; PubMed Central PMCID: PMC2800175.
7: Hatsu M, Sasaki T, Watabe H, Miyadoh S, Nagasawa M, Shomura T, Sezaki M, Inouye S, Kondo S. A new tetracycline antibiotic with antitumor activity. I. Taxonomy and fermentation of the producing strain, isolation and characterization of SF2575. J Antibiot (Tokyo). 1992 Mar;45(3):320-4. PubMed PMID: 1577660.
