WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H200580
CAS#: 203258-38-2 (HCl)
Description: Brostallicin is a synthetic, alpha-bromoacrylic, second-generation minor groove binder (MGB), related to distamycin A, with potential antineoplastic activity. Brostallicin binds to DNA minor groove DNA, after having formed a highly reactive glutathione (GSH)-brostallicin complex in the presence of the enzyme glutathione S-transferase (GST), which is overexpressed in cancer cells; DNA replication and cell division are inhibited, resulting in tumor cell death. Compared to typical MGBs, this agent appears to bind covalently to DNA in a different manner and its activity does not depend on a functional DNA mismatch repair (MMR) mechanism. Accordingly, brostallicin may be effective against MMR-defective tumors that are refractory to various anticancer agents.
Hodoodo Cat#: H200580
Name: Brostallicin HCl
CAS#: 203258-38-2 (HCl)
Chemical Formula: C30H36BrClN12O5
Exact Mass: 0.00
Molecular Weight: 760.040
Elemental Analysis: C, 47.41; H, 4.77; Br, 10.51; Cl, 4.66; N, 22.11; O, 10.53
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Related CAS #: 203258-60-0 (free base) 203258-38-2 (HCl)
Synonym: PNU166196; PNU-166196; PNU 166196; Brostallicin HCl; Brostallicin hydrochloride;
IUPAC/Chemical Name: 4-(2-bromoacrylamido)-N-(5-((5-((5-((2-guanidinoethyl)carbamoyl)-1-methyl-1H-pyrrol-3-yl)carbamoyl)-1-methyl-1H-pyrrol-3-yl)carbamoyl)-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide hydrochloride
InChi Key: IPKHXIAPPAKHTB-UHFFFAOYSA-N
InChi Code: InChI=1S/C30H35BrN12O5.ClH/c1-16(31)25(44)36-17-9-22(41(3)12-17)27(46)38-19-11-24(43(5)14-19)29(48)39-20-10-23(42(4)15-20)28(47)37-18-8-21(40(2)13-18)26(45)34-6-7-35-30(32)33;/h8-15H,1,6-7H2,2-5H3,(H,34,45)(H,36,44)(H,37,47)(H,38,46)(H,39,48)(H4,32,33,35);1H
SMILES Code: O=C(C1=CC(NC(C(Br)=C)=O)=CN1C)NC2=CN(C)C(C(NC3=CN(C)C(C(NC4=CN(C)C(C(NCCNC(N)=N)=O)=C4)=O)=C3)=O)=C2.[H]Cl
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, not in water
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
More Info: Related: 203258-38-2 (Brostallicin HCl salt) 203258-60-0 (Brostallicin free base). Brostallicin is a synthetic, alpha-bromoacrylic, second-generation minor groove binder (MGB), related to distamycin A, with potential antineoplastic activity. Brostallicin binds to DNA minor groove DNA, after having formed a highly reactive glutathione (GSH)-brostallicin complex in the presence of the enzyme glutathione S-transferase (GST), which is overexpressed in cancer cells; DNA replication and cell division are inhibited, resulting in tumor cell death. Compared to typical MGBs, this agent appears to bind covalently to DNA in a different manner and its activity does not depend on a functional DNA mismatch repair (MMR) mechanism. Accordingly, brostallicin may be effective against MMR-defective tumors that are refractory to various anticancer agents. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus) Current developer:
Biological target: | |
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The following data is based on the product molecular weight 760.04 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. Lorusso, Domenica; Mainenti, Sara; Pietragalla, Antonella; Ferrandina, Gabriella; Foco, Gilda; Masciullo, Valeria; Scambia, Giovanni. Brostallicin (PNU-166196), a new minor groove DNA binder: preclinical and clinical activity. Expert Opinion on Investigational Drugs (2009), 18(12), 1939-1946. CODEN: EOIDER ISSN:1354-3784. CAN 152:110619 AN 2009:1472481
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7. Romagnoli, Romeo; Baraldi, Pier Giovanni; Cruz-Lopez, Olga; Preti, Delia; Bermejo, Jaime; Estevez, Francisco. -Bromoacrylamido N-Substituted Isatin Derivatives as Potent Inducers of Apoptosis in Human Myeloid Leukemia Cells. ChemMedChem (2009), 4(10), 1668-1676. CODEN: CHEMGX ISSN:1860-7179. CAN 152:51175 AN 2009:1215039
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