TANDEM (quinoxaline) | CAS#63478-55-7 | quinoxaline analog

MedKoo Cat#: 598125 | Name: TANDEM (quinoxaline)

Description:

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

TANDEM (quinoxaline) is a synthetic analog of quinoxaline antibiotics.

Chemical Structure

TANDEM (quinoxaline)

CAS#63478-55-7

Theoretical Analysis

MedKoo Cat#: 598125

Name: TANDEM (quinoxaline)

CAS#: 63478-55-7

Chemical Formula: C46H54N12O12S2

Exact Mass: 1030.3426

Molecular Weight: 1031.13

Elemental Analysis: C, 53.58; H, 5.28; N, 16.30; O, 18.62; S, 6.22

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

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

Instruction

View handling instruction

Preparing Stock Solutions

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

1: Sung KW, Lim DH, Lee SH, Yoo KH, Koo HH, Kim JH, Suh YL, Joung YS, Shin HJ. Tandem high-dose chemotherapy and autologous stem cell transplantation for anaplastic ependymoma in children younger than 3 years of age. J Neurooncol. 2012 Apr;107(2):335-42. doi: 10.1007/s11060-011-0745-8. Epub 2011 Nov 12. PubMed PMID: 22081297. 2: Hampshire AJ, Rusling DA, Bryan S, Paumier D, Dawson SJ, Malkinson JP, Searcey M, Fox KR. DNA binding by analogues of the bifunctional intercalator TANDEM. Biochemistry. 2008 Jul 29;47(30):7900-6. doi: 10.1021/bi800573p. Epub 2008 Jul 3. PubMed PMID: 18597492. 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. 5: Evans DH, Lee JS, Morgan AR, Olsen RK. A method for the specific inhibition of poly[d(A-T)] synthesis using the A-T specific quinoxaline antibiotic TANDEM. Can J Biochem. 1982 Feb;60(2):131-6. PubMed PMID: 7044498. 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. 13: Fox KR, Olsen RK, Waring MJ. Interaction between synthetic analogues of quinoxaline antibiotics and nucleic acids: role of the disulphide cross-bridge and D-amino acid centres in des-N-tetramethyl-triostin A. Br J Pharmacol. 1980 Sep;70(1):25-40. PubMed PMID: 7426829; PubMed Central PMCID: PMC2044367. 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. 17: Cui X, Shao B, Zhao R, Meng J, Tu X. [Simultaneous determination of twelve glucocorticoids residues in milk by ultra performance liquid chromatography-electrospray tandem mass spectrometry]. Se Pu. 2006 May;24(3):213-7. Chinese. PubMed PMID: 16929834. 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. 20: Lorenz KB, Diederichsen U. Solution-phase synthesis of nucleobase-substituted analogues of triostin A. J Org Chem. 2004 May 28;69(11):3917-27. PubMed PMID: 15153026.