WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H598125
CAS#: 63478-55-7
Description: TANDEM (quinoxaline) is a synthetic analog of quinoxaline antibiotics.
Hodoodo Cat#: H598125
Name: TANDEM (quinoxaline)
CAS#: 63478-55-7
Chemical Formula: C46H54N12O12S2
Exact Mass: 1,030.34
Molecular Weight: 1,031.130
Elemental Analysis: C, 53.58; H, 5.28; N, 16.30; O, 18.62; S, 6.22
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Synonym: TANDEM (quinoxaline); Tandem;
IUPAC/Chemical Name: N,N'-((1R,4S,7R,11S,14S,17S,20S,24S)-4,17-dimethyl-3,6,10,13,16,19,23,26-octaoxo-11,24-dipropyl-9,22-dioxa-28,29-dithia-2,5,12,15,18,25-hexaazabicyclo[12.12.4]triacontane-7,20-diyl)bis(quinoxaline-2-carboxamide)
InChi Key: JLZYVPLGZIDPEB-WMTRIAHWSA-N
InChi Code: InChI=1S/C46H54N12O12S2/c1-5-11-29-45(67)69-19-33(55-39(61)31-17-47-25-13-7-9-15-27(25)51-31)41(63)49-24(4)38(60)58-36-22-72-71-21-35(43(65)53-29)57-37(59)23(3)50-42(64)34(20-70-46(68)30(12-6-2)54-44(36)66)56-40(62)32-18-48-26-14-8-10-16-28(26)52-32/h7-10,13-18,23-24,29-30,33-36H,5-6,11-12,19-22H2,1-4H3,(H,49,63)(H,50,64)(H,53,65)(H,54,66)(H,55,61)(H,56,62)(H,57,59)(H,58,60)/t23-,24-,29-,30-,33-,34+,35-,36+/m0/s1
SMILES Code: O=C1N[C@H](C(N[C@@H]2CSSC[C@H](NC([C@H](C)NC([C@H](NC(c3cnc4ccccc4n3)=O)COC([C@H](CCC)NC2=O)=O)=O)=O)C(N[C@H](C(OC[C@@H]1NC(c(n5)cnc6c5cccc6)=O)=O)CCC)=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: |
The following data is based on the product molecular weight 1,031.13 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
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3: Hampshire AJ, Fox KR. Preferred binding sites for the bifunctional intercalator TANDEM determined using DNA fragments that contain every symmetrical hexanucleotide sequence. Anal Biochem. 2008 Mar 15;374(2):298-303. Epub 2007 Oct 11. PubMed PMID: 17980140.
4: Hammond NB, Tolbert BS, Kierzek R, Turner DH, Kennedy SD. RNA internal loops with tandem AG pairs: the structure of the 5'GAGU/3'UGAG loop can be dramatically different from others, including 5'AAGU/3'UGAA. Biochemistry. 2010 Jul 13;49(27):5817-27. doi: 10.1021/bi100332r. PubMed PMID: 20481618; PubMed Central PMCID: PMC2900907.
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6: Malkinson JP, Anim MK, Zloh M, Searcey M, Hampshire AJ, Fox KR. Efficient solid-phase-based total synthesis of the bisintercalator TANDEM. J Org Chem. 2005 Sep 16;70(19):7654-61. PubMed PMID: 16149796.
7: Lavesa M, Fox KR. Preferred binding sites for [N-MeCYs(3), N-MeCys(7)]TANDEM determined using a universal footprinting substrate. Anal Biochem. 2001 Jun 15;293(2):246-50. PubMed PMID: 11399039.
8: Addess KJ, Gilbert DE, Olsen RK, Feigon J. Proton NMR studies of [N-MeCys3,N-MeCys7]TANDEM binding to DNA oligonucleotides: sequence-specific binding at the TpA site. Biochemistry. 1992 Jan 21;31(2):339-50. PubMed PMID: 1731892.
9: Powers R, Olsen RK, Gorenstein DG. Two-dimensional 1H and 31P NMR spectra of a decamer oligodeoxyribonucleotide duplex and a quinoxaline ((MeCys3, MeCys7)(TANDEM) drug duplex complex. J Biomol Struct Dyn. 1989 Dec;7(3):515-56. PubMed PMID: 2627298.
10: Viswamitra MA, Kennard O, Cruse WB, Egert E, Sheldrick GM, Jones PG, Waring MJ, Wakelin LP, Olsen RK. Structure of TANDEM and its implication for bifunctional intercalation into DNA. Nature. 1981 Feb 26;289(5800):817-9. PubMed PMID: 7464949.
11: Bailly C, Waring MJ. DNA recognition by quinoxaline antibiotics: use of base-modified DNA molecules to investigate determinants of sequence-specific binding of triostin A and TANDEM. Biochem J. 1998 Feb 15;330 ( Pt 1):81-7. PubMed PMID: 9461494; PubMed Central PMCID: PMC1219111.
12: Alfredson TV, Maki AH, Adaskaveg ME, Excoffier JL, Waring MJ. Liquid chromatographic investigation of quinoxaline antibiotics and their analogues by means of ultraviolet diode-array detection. J Chromatogr. 1990 May 16;507:277-92. PubMed PMID: 2380298.
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14: Low CM, Olsen RK, Waring MJ. Sequence preferences in the binding to DNA of triostin A and TANDEM as reported by DNase I footprinting. FEBS Lett. 1984 Oct 29;176(2):414-20. PubMed PMID: 6386526.
15: Bessette EE, Yasa I, Dunbar D, Wilkens LR, Le Marchand L, Turesky RJ. Biomonitoring of carcinogenic heterocyclic aromatic amines in hair: a validation study. Chem Res Toxicol. 2009 Aug;22(8):1454-63. doi: 10.1021/tx900155f. PubMed PMID: 19588936; PubMed Central PMCID: PMC2787961.
16: Low CM, Fox KR, Olsen RK, Waring MJ. DNA sequence recognition by under-methylated analogues of triostin A. Nucleic Acids Res. 1986 Mar 11;14(5):2015-33. PubMed PMID: 3008083; PubMed Central PMCID: PMC339640.
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18: Waring MJ. Echinomycin. Pathol Biol (Paris). 1992 Dec;40(10):1022-34. Review. PubMed PMID: 1299809.
19: Fox KR, Olsen RK, Waring MJ. Equilibrium and kinetic studies on the binding of des-N-tetramethyltriostin A to DNA. Biochim Biophys Acta. 1982 Mar 29;696(3):315-22. PubMed PMID: 7066328.
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