WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406188
CAS#: 108307-65-9
Description: RB-90740 is an aromatic mono-N-oxide bioreductive drug, which showed considerably greater toxicity towards hypoxic verses aerobic mammalian cells in vitro. The differential in concentration required to give the same level of cell killing under these conditions ranges from 3.5 in a human bronchio-alveolar tumor cell line up to 120 in a rodent cell line defective in the repair of DNA strand breaks. The ability of RB 90740 to cause DNA strand breaks under hypoxic conditions was confirmed by alkaline sucrose gradient and pulsed field gel electrophoresis techniques.
MedKoo Cat#: 406188
Name: RB-90740
CAS#: 108307-65-9
Chemical Formula: C20H22N6O
Exact Mass: 362.18551
Molecular Weight: 362.43
Elemental Analysis: C, 66.28; H, 6.12; N, 23.19; O, 4.41
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Synonym: RB90740; RB 90740; RB-90740
IUPAC/Chemical Name: Imidazo[1,2-a]pyrido[3,2-e]pyrazine, 8,9-dihydro-2-(4-methyl-1-piperazinyl)-6-phenyl-, 5-oxide
InChi Key: CKRPRSXFNWNTOW-UHFFFAOYSA-N
InChi Code: InChI=1S/C20H22N6O/c1-23-11-13-24(14-12-23)17-8-7-16-19(22-17)25-10-9-21-20(25)18(26(16)27)15-5-3-2-4-6-15/h2-8H,9-14H2,1H3
SMILES Code: CN1CCN(C2=CC=C3[N+]([O-])=C(C4=CC=CC=C4)C5=NCCN5C3=N2)CC1
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: >5 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
The following data is based on the product molecular weight 362.43 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: Urquiola C, Vieites M, Torre MH, Cabrera M, Lavaggi ML, Cerecetto H, González M, Cerain AL, Monge A, Smircich P, Garat B, Gambino D. Cytotoxic palladium complexes of bioreductive quinoxaline N1,N4-dioxide prodrugs. Bioorg Med Chem. 2009 Feb 15;17(4):1623-9. doi: 10.1016/j.bmc.2008.12.064. Epub 2009 Jan 3. PubMed PMID: 19162490.
2: Barham HM, Inglis R, Chinje EC, Stratford IJ. Development and validation of a spectrophotometric assay for measuring the activity of NADH: cytochrome b5 reductase in human tumour cells. Br J Cancer. 1996 Oct;74(8):1188-93. PubMed PMID: 8883403; PubMed Central PMCID: PMC2075922.
3: Wardman P, Priyadarsini KI, Dennis MF, Everett SA, Naylor MA, Patel KB, Stratford IJ, Stratford MR, Tracy M. Chemical properties which control selectivity and efficacy of aromatic N-oxide bioreductive drugs. Br J Cancer Suppl. 1996 Jul;27:S70-4. PubMed PMID: 8763850; PubMed Central PMCID: PMC2150009.
4: Hei TK, Liu SX, Hall EJ. Oncogenic potential of bifunctional bioreductive drugs. Br J Cancer Suppl. 1996 Jul;27:S57-60. PubMed PMID: 8763847; PubMed Central PMCID: PMC2150017.
5: Barham HM, Stratford IJ. Enzymology of the reduction of the novel fused pyrazine mono-n-oxide bioreductive drug, RB90740 roles for P450 reductase and cytochrome b5 reductase. Biochem Pharmacol. 1996 Mar 22;51(6):829-37. PubMed PMID: 8602879.
6: Langmuir VK, Laderoute KR, Mendonca HL, Sutherland RM, Hei TK, Liu SX, Hall EJ, Naylor MA, Adams GE. Fused pyrazine mono-n-oxides as bioreductive drugs. II Cytotoxicity in human cells and oncogenicity in a rodent transformation assay. Int J Radiat Oncol Biol Phys. 1996 Jan 1;34(1):79-84. PubMed PMID: 12118568.
7: Naylor MA, Adams GE, Haigh A, Cole S, Jenner T, Robertson N, Siemann D, Stephens MA, Stratford IJ. Fused pyrazine mono-N-oxides as bioreductive drugs. III. Characterization of RB 90740 in vitro and in vivo. Anticancer Drugs. 1995 Apr;6(2):259-69. PubMed PMID: 7795274.
8: Sutton BM, Reeves NJ, Naylor MA, Fielden EM, Cole S, Adams GE, Stratford IJ. Pharmacokinetics, metabolism and distribution of 1,2-dihydro-8-(4-methylpiperazinyl)-4-phenylimidazo [1,2-A] pyrido [3,2-E] pyrazine-5-oxide in C3H mice. Int J Radiat Oncol Biol Phys. 1994 May 15;29(2):339-44. PubMed PMID: 8195030.
9: Naylor MA, Sutton BM, Nolan J, O'Neill P, Fielden EM, Adams GE, Stratford IJ. Radiolytic and photochemical reduction of the hypoxic cytotoxin 1,2-dihydro-8-(4-methylpiperazinyl)-4-phenylimidazo [1,2-a] pyrido [3,2-e] pyrazine 5-oxide (RB90740) and a potential mechanism for hypoxia-selective toxicity. Int J Radiat Oncol Biol Phys. 1994 May 15;29(2):333-7. PubMed PMID: 8195029.
10: Bremner JC, Bradley JK, Adams GE, Naylor MA, Sansom JM, Stratford IJ. Comparing the anti-tumor effect of several bioreductive drugs when used in combination with photodynamic therapy (PDT). Int J Radiat Oncol Biol Phys. 1994 May 15;29(2):329-32. PubMed PMID: 8195028.
11: Naylor MA. Novel N-oxides as bioreductive drugs. Oncol Res. 1994;6(10-11):483-91. Review. PubMed PMID: 7620216.
