WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H591662
CAS#: 145124-30-7 (dimesylate)
Description: Bisnafide is a Naphthalimide Analogue that acts as DNA intercalator and topo II inhibitor. It is also an antiangiogenic agent. Antiangiogenic agents can normalize tumor vessels and promote the delivery of cytotoxic agents to tumor sites.
Hodoodo Cat#: H591662
Name: Bisnafide mesylate
CAS#: 145124-30-7 (dimesylate)
Chemical Formula: C34H36N6O14S2
Exact Mass: 816.17
Molecular Weight: 816.810
Elemental Analysis: C, 50.00; H, 4.44; N, 10.29; O, 27.42; S, 7.85
Related CAS #: 145124-30-7 (dimesylate) 144849-63-8 (free base),
Synonym: Bisnafide mesylate; DMP840; DMP-840; DMP 840
IUPAC/Chemical Name: 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)
InChi Key: KPQJSSLKKBKWEW-RKDOVGOJSA-N
InChi Code: 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
SMILES Code: 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
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: >2 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
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 816.81 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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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.
