Bisnafide mesylate| CAS# 145124-30-7 | topo II inhibitor

MedKoo Cat#: 591662 | Name: Bisnafide mesylate

Description:

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

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.

Chemical Structure

Bisnafide mesylate

CAS#145124-30-7 (dimesylate)

Theoretical Analysis

MedKoo Cat#: 591662

Name: Bisnafide mesylate

CAS#: 145124-30-7 (dimesylate)

Chemical Formula: C34H36N6O14S2

Exact Mass: 0.0000

Molecular Weight: 816.81

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

Price and Availability

Size	Price	Availability
1mg	USD 90.00	Ready to Ship
5mg	USD 250.00	Ready to Ship
10mg	USD 450.00	Ready to Ship
25mg	USD 750.00	Ready to Ship
50mg	USD 1,350.00	Ready to Ship
100mg	USD 2,350.00	Ready to Ship

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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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#Y22X12M02

QC Data

View QC data: current batch, Lot#Y22X12M02

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Bisnafide acts as DNA intercalator and topo II inhibitor.

In vitro activity:

TBD

In vivo activity:

TBD

Preparing Stock Solutions

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:

TBD

In vitro protocol:

TBD

In vivo protocol:

TBD

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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.