1: Antonini I, Santoni G, Lucciarini R, Amantini C, Sparapani S, Magnano A. Synthesis and biological evaluation of new asymmetrical bisintercalators as potential antitumor drugs. J Med Chem. 2006 Nov 30;49(24):7198-207. doi: 10.1021/jm0606793. PMID: 17125272. 2: Adams MA, Iannuzzi P, Jia Z. MdaB from Escherichia coli: cloning, purification, crystallization and preliminary X-ray analysis. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2005 Feb 1;61(Pt 2):235-8. doi: 10.1107/S1744309105001545. Epub 2005 Feb 1. PMID: 16511004; PMCID: PMC1952255. 3: Carrasco C, Joubert A, Tardy C, Maestre N, Cacho M, Braña MF, Bailly C. DNA sequence recognition by bispyrazinonaphthalimides antitumor agents. Biochemistry. 2003 Oct 14;42(40):11751-61. doi: 10.1021/bi034637h. PMID: 14529286. 4: Bailly C, Carrasco C, Joubert A, Bal C, Wattez N, Hildebrand MP, Lansiaux A, Colson P, Houssier C, Cacho M, Ramos A, Braña MF. Chromophore-modified bisnaphthalimides: DNA recognition, topoisomerase inhibition, and cytotoxic properties of two mono- and bisfuronaphthalimides. Biochemistry. 2003 Apr 15;42(14):4136-50. doi: 10.1021/bi027415c. PMID: 12680768. 5: Rubino JT, Chan LL, Walker JT, Segretario J, Everlof JG, Hussain MA. Photoinduced particulate matter in a parenteral formulation for bisnafide, an experimental antitumor agent. Pharm Dev Technol. 1999 Aug;4(3):439-47. doi: 10.1081/pdt-100101380. PMID: 10434290. 6: Ghaneolhosseini H, Sjöberg S. Synthesis of a boronated naphthalimide for potential use in boron neutron capture therapy (BNCT). Acta Chem Scand (Cph). 1999 Apr;53(4):298-300. doi: 10.3891/acta.chem.scand.53-0298. PMID: 10214688. 7: Segretario J, Cook SC, Umbles CL, Walker JT, Woodeshick RW, Rubino JT, Shea JA. Validation of cleaning procedures for highly potent drugs. II. Bisnafide. Pharm Dev Technol. 1998 Nov;3(4):471-6. doi: 10.3109/10837459809028628. PMID: 9834949. 8: Thompson J, Pratt CB, Stewart CF, Avery L, Bowman L, Zamboni WC, Pappo A. Phase I study of DMP 840 in pediatric patients with refractory solid tumors. Invest New Drugs. 1998;16(1):45-9. doi: 10.1023/a:1006014510078. PMID: 9740543. 9: Lai CM, Garner DM, Gray JE, Brogdon BL, Peterman VC, Pieniaszek HJ Jr. Determination of bisnafide, a novel bis-naphthalimide anticancer agent, in human plasma by high-performance liquid chromatography with UV detection. J Pharm Biomed Anal. 1998 Jul;17(3):427-34. doi: 10.1016/s0731-7085(97)00232-x. PMID: 9656154. 10: O'Reilly S, Baker SD, Sartorius S, Rowinsky EK, Finizio M, Lubiniecki GM, Grochow LB, Gray JE, Pieniaszek HJ Jr, Donehower RC. A phase I and pharmacologic study of DMP 840 administered by 24-hour infusion. Ann Oncol. 1998 Jan;9(1):101-4. doi: 10.1023/a:1008260515869. PMID: 9541690. 11: Nitiss JL, Zhou J, Rose A, Hsiung Y, Gale KC, Osheroff N. The bis(naphthalimide) DMP-840 causes cytotoxicity by its action against eukaryotic topoisomerase II. Biochemistry. 1998 Mar 3;37(9):3078-85. doi: 10.1021/bi9723257. PMID: 9485461. 12: Rubino JT, Nellore R, Parmar B. Dynamic compatibility testing of DMP 840, an experimental antitumor agent. PDA J Pharm Sci Technol. 1997 May-Jun;51(3):130-6. PMID: 9203827. 13: Raghavan KS, Nemeth GA, Gray DB, Hussain MA. Solubility enhancement of a bisnaphthalimide tumoricidal agent, DMP 840, through complexation. Pharm Dev Technol. 1996 Oct;1(3):231-8. doi: 10.3109/10837459609022591. PMID: 9552305. 14: Chatterjee PK, Sternberg NL. A general genetic approach in Escherichia coli for determining the mechanism(s) of action of tumoricidal agents: application to DMP 840, a tumoricidal agent. Proc Natl Acad Sci U S A. 1995 Sep 12;92(19):8950-4. doi: 10.1073/pnas.92.19.8950. PMID: 7568050; PMCID: PMC41085. 15: Pratt CB, Rao BN, Stewart CF, Jenkins JJ 3rd. Successful treatment of metastatic choriocarcinoma after DMP 840. Urol Oncol. 1995 Jul-Aug;1(4):166-7. doi: 10.1016/1078-1439(95)00042-9. PMID: 21224112. 16: Chatterjee PK, Sternberg NL. Using cell-fractionation and photochemical crosslinking methods to determine the cellular binding site(s) of the antitumor drug DMP 840. Photochem Photobiol. 1995 Apr;61(4):360-6. doi: 10.1111/j.1751-1097.1995.tb08623.x. PMID: 7740079. 17: LoRusso P, Demchik L, Dan M, Polin L, Gross JL, Corbett TH. Comparative efficacy of DMP 840 against mouse and human solid tumor models. Invest New Drugs. 1995;13(3):195-203. doi: 10.1007/BF00873800. PMID: 8729946. 18: Cobb PW, Degen DR, Clark GM, Chen SF, Kuhn JG, Gross JL, Kirshenbaum MR, Sun JH, Burris HA 3rd, Von Hoff DD. Activity of DMP 840, a new bis-naphthalimide, on primary human tumor colony-forming units. J Natl Cancer Inst. 1994 Oct 5;86(19):1462-5. doi: 10.1093/jnci/86.19.1462. PMID: 8089865. 19: Kirshenbaum MR, Chen SF, Behrens CH, Papp LM, Stafford MM, Sun JH, Behrens DL, Fredericks JR, Polkus ST, Sipple P, et al. (R,R)-2,2'-[1,2-ethanediylbis[imino(1-methyl-2,1-ethanediyl)]]- bis[5-nitro-1H-benz[de]isoquinoline-1,3-(2H)-dione] dimethanesulfonate (DMP 840), a novel bis-naphthalimide with potent nonselective tumoricidal activity in vitro. Cancer Res. 1994 Apr 15;54(8):2199-206. PMID: 8174127. 20: Houghton PJ, Cheshire PJ, Hallman JC 3rd, Gross JL, McRipley RJ, Sun JH, Behrens CH, Dexter DL, Houghton JA. Evaluation of a novel bis-naphthalimide anticancer agent, DMP 840, against human xenografts derived from adult, juvenile, and pediatric cancers. Cancer Chemother Pharmacol. 1994;33(4):265-72. doi: 10.1007/BF00685898. PMID: 8281618.

C34H36N6O14S2

816.81

816.17

C, 50.00; H, 4.44; N, 10.29; O, 27.42; S, 7.85

145124-30-7

145124-30-7 (dimesylate);144849-63-8;

C[C@@H](N(C(C1=CC([N+]([O-])=O)=CC2=CC=CC3=C12)=O)C3=O)CNCCNC[C@H](N(C(C4=CC([N+]([O-])=O)=CC5=CC=CC6=C45)=O)C6=O)C.CS(=O)(O)=O.CS(=O)(O)=O

KPQJSSLKKBKWEW-RKDOVGOJSA-N

InChI=1S/C32H28N6O8.2CH4O3S/c1-17(35-29(39)23-7-3-5-19-11-21(37(43)44)13-25(27(19)23)31(35)41)15-33-9-10-34-16-18(2)36-30(40)24-8-4-6-20-12-22(38(45)46)14-26(28(20)24)32(36)42;2*1-5(2,3)4/h3-8,11-14,17-18,33-34H,9-10,15-16H2,1-2H3;2*1H3,(H,2,3,4)/t17-,18-;;/m1../s1

1H-Benz[de]isoquinoline-1,3(2H)-dione, 2,2′-[1,2-ethanediylbis[imino[(1R)-1-methyl-2,1-ethanediyl]]]bis[5-nitro-, methanesulfonate (1:2)

Bisnafide mesylate; DMP840; DMP-840; DMP 840

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)