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MedKoo Cat#: 126276 | Name: Brostallicin

Description:

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

Brostallicin is a DNA minor groove binder which has shown very promising preclinical activity against a variety of human tumors both in vitro and in vivo.

Chemical Structure

Brostallicin
Brostallicin
CAS#203258-60-0 (free base)

Theoretical Analysis

MedKoo Cat#: 126276

Name: Brostallicin

CAS#: 203258-60-0 (free base)

Chemical Formula: C30H35BrN12O5

Exact Mass: 722.2037

Molecular Weight: 723.59

Elemental Analysis: C, 49.80; H, 4.88; Br, 11.04; N, 23.23; O, 11.06

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
203258-60-0 (free base) 203258-38-2 (HCl)
Synonym
PNU-166196A; PNU166196; Brostallicin;
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
InChi Key
RXOVOXFAAGIKDQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C30H35BrN12O5/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)
SMILES Code
CN1C=C(NC(=O)C2=CC(NC(=O)C3=CC(NC(=O)C4=CC(NC(=O)C(Br)=C)=CN4C)=CN3C)=CN2C)C=C1C(=O)NCCNC(N)=N
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 723.59 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.

Recalculate based on batch purity %
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. Caponigro, F.; Lorusso, D.; Fornari, G.; Barone, C.; Merlano, M.; Airoldi, M.; Schena, M.; MacArthur, R.; Weitman, S.; Jannuzzo, M. G.; Crippa, S.; Fiorentini, F.; Petroccione, A.; Comis, S. Phase I dose-escalation study of brostallicin, a minor groove binder, in combination with cisplatin in patients with advanced solid tumors. Cancer Chemotherapy and Pharmacology (2010), 66(2), 389-394. CODEN: CCPHDZ ISSN:0344-5704. AN 2010:622626 2. Pezzola, Silvia; Antonini, Giovanni; Geroni, Cristina; Beria, Italo; Colombo, Maristella; Broggini, Massimo; Marchini, Sergio; Mongelli, Nicola; Leboffe, Loris; MacArthur, Robert; Mozzi, Alessia Francesca; Federici, Giorgio; Caccuri, Anna Maria. Correction to Role of Glutathione Transferases in the Mechanism of Brostallicin Activation. Biochemistry (2010), 49(23), 4930. CODEN: BICHAW ISSN:0006-2960. AN 2010:618736 3. Rickles, Richard; Lee, Margaret S.  -Adrenergic receptor agonists for the treatment of B-cell proliferative disorders. PCT Int. Appl. (2009), 111 pp. CODEN: PIXXD2 WO 2009151569 A2 20091217 CAN 152:67621 AN 2009:1566750 4. Pezzola, Silvia; Antonini, Giovanni; Geroni, Cristina; Beria, Italo; Colombo, Maristella; Broggini, Massimo; Mongelli, Nicola; Leboffe, Loris; MacArthur, Robert; Mozzi, Alessia Francesca; Federici, Giorgio; Caccuri, Anna Maria. Role of Glutathione Transferases in the Mechanism of Brostallicin Activation. Biochemistry (2010), 49(1), 226-235. CODEN: BICHAW ISSN:0006-2960. CAN 152:111089 AN 2009:1537627 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 6. Bruckheimer, Elizabeth; Kiefer, Jeff; Mousses, Spyro; Shanmugam, Kandavel; Yin, Hongwei; Weitman, Steve. Target expression-based method for assessing sensitivity to brostallicin. PCT Int. Appl. (2009), 66pp. CODEN: PIXXD2 WO 2009126970 A1 20091015 CAN 151:440645 AN 2009:1262339 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 8. Guirouilh-Barbat, Josee; Zhang, Yong-Wei; Pommier, Yves. Induction of glutathione-dependent DNA double-strand breaks by the novel anticancer drug brostallicin. Molecular Cancer Therapeutics (2009), 8(7), 1985-1994. CODEN: MCTOCF ISSN:1535-7163. CAN 151:279230 AN 2009:848543 9. Romagnoli, Romeo; Baraldi, Pier Giovanni; Cruz-Lopez, Olga; Lopez-Cara, Carlota; Preti, Delia.  -halogenoacrylic derivatives of antitumor agents. Mini-Reviews in Medicinal Chemistry (2009), 9(1), 81-94. CODEN: MMCIAE ISSN:1389-5575. CAN 151:310 AN 2009:460861 10. Rickles, Richard; Lee, Margaret S. Use of adenosine A2A receptor agonists and phosphodiesterase (PDE) inhibitors for the treatment of B-cell proliferative disorders, and combinations with other agents. PCT Int. Appl. (2009), 70 pp. CODEN: PIXXD2 WO 2009011893 A2 20090122 CAN 150:160095 AN 2009:86451