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232931-57-6,MFCD19443671
Catalog No.:AA002MQ9

232931-57-6 | SJG-136

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1mg
98%
in stock  
$355.00   $249.00
- +
2mg
98%
in stock  
$489.00   $342.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002MQ9
Chemical Name:
SJG-136
CAS Number:
232931-57-6
Molecular Formula:
C31H32N4O6
Molecular Weight:
556.6090
MDL Number:
MFCD19443671
SMILES:
COc1cc2c(cc1OCCCOc1cc3N=C[C@H]4N(C(=O)c3cc1OC)CC(=C)C4)N=C[C@H]1N(C2=O)CC(=C)C1
NSC Number:
694501
Properties
Computed Properties
 
Complexity:
1020  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
41  
Hydrogen Bond Acceptor Count:
8  
Rotatable Bond Count:
8  
XLogP3:
1.9  

Upstream Synthesis Route

[1]Patent:WO2010/43877,2010,A1,.Locationinpatent:Page/Pagecolumn54;56

[1]JournalofMedicinalChemistry,2001,vol.44,#5,p.737-748

[2]Patent:EP1193270,2002,A2,.Locationinpatent:Page53-54,54-55,111,112

[1]JournalofMedicinalChemistry,2001,vol.44,#5,p.737-748

[1]JournalofMedicinalChemistry,2001,vol.44,#5,p.737-748

[1]JournalofMedicinalChemistry,2001,vol.44,#5,p.737-748

Downstream Synthesis Route

[1]JournalofMedicinalChemistry,2001,vol.44,p.737-748

[2]Patent:EP1193270,2002,A2.Locationinpatent:Page53-54,54-55,111,112

[1]JournalofMedicinalChemistry,2001,vol.44,p.737-748

[1]JournalofMedicinalChemistry,2001,vol.44,p.737-748

C19H16Cl2N2O10 
  232931-57-6 

[1]JournalofMedicinalChemistry,2001,vol.44,p.737-748

[1]JournalofMedicinalChemistry,2001,vol.44,p.737-748

Literature

Title: Small molecule drugs - optimizing DNA damaging agent-based therapeutics.

Journal: Current opinion in pharmacology 20120801

Title: Pharmacokinetics, pharmacodynamics and metabolism of the dimeric pyrrolobenzodiazepine SJG-136 in rats.

Journal: Cancer chemotherapy and pharmacology 20110901

Title: Phase I pharmacokinetic and pharmacodynamic study of SJG-136, a novel DNA sequence selective minor groove cross-linking agent, in advanced solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110601

Title: The development of pyrrolobenzodiazepines as antitumour agents.

Journal: Expert opinion on investigational drugs 20110601

Title: A phase I trial of SJG-136 (NSC#694501) in advanced solid tumors.

Journal: Cancer chemotherapy and pharmacology 20100401

Title: Synthesis of a novel C2/C2'-aryl-substituted pyrrolo[2,1-c][1,4]benzodiazepine dimer prodrug with improved water solubility and reduced DNA reaction rate.

Journal: Bioorganic & medicinal chemistry letters 20091115

Title: The pyrrolobenzodiazepine dimer SJG-136 forms sequence-dependent intrastrand DNA cross-links and monoalkylated adducts in addition to interstrand cross-links.

Journal: Journal of the American Chemical Society 20090930

Title: Phase I study of sequence-selective minor groove DNA binding agent SJG-136 in patients with advanced solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090315

Title: Remarkable enhancement in the DNA-binding ability of C2-fluoro substituted pyrrolo[2,1-c][1,4]benzodiazepines and their anticancer potential.

Journal: Bioorganic & medicinal chemistry 20090215

Title: ABCB1 genetic polymorphism influences the pharmacology of the new pyrrolobenzodiazepine derivative SJG-136.

Journal: The pharmacogenomics journal 20080801

Title: An asymmetric C8/C8'-tripyrrole-linked sequence-selective pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimer DNA interstrand cross-linking agent spanning 11 DNA base pairs.

Journal: Bioorganic & medicinal chemistry letters 20080315

Title: An assay combining high-performance liquid chromatography and mass spectrometry to measure DNA interstrand cross-linking efficiency in oligonucleotides of varying sequences.

Journal: Analytical biochemistry 20080301

Title: Determination of chemically reduced pyrrolobenzodiazepine SJG-136 in human plasma by HPLC-MS/MS: application to an anticancer phase I dose escalation study.

Journal: Journal of mass spectrometry : JMS 20080101

Title: Fludarabine-mediated suppression of the excision repair enzyme ERCC1 contributes to the cytotoxic synergy with the DNA minor groove crosslinking agent SJG-136 (NSC 694501) in chronic lymphocytic leukaemia cells.

Journal: British journal of cancer 20070716

Title: The hollow fibre model--facilitating anti-cancer pre-clinical pharmacodynamics and improving animal welfare.

Journal: International journal of oncology 20061201

Title: DNA interstrand crosslinking agents: synthesis, DNA interactions, and cytotoxicity of dimeric achiral seco-amino-CBI and conjugates of achiral seco-amino-CBI with pyrrolobenzodiazepine (PBD).

Journal: Bioorganic & medicinal chemistry letters 20061101

Title: Design, synthesis, and biophysical and biological evaluation of a series of pyrrolobenzodiazepine-poly(N-methylpyrrole) conjugates.

Journal: Journal of medicinal chemistry 20060907

Title: LC-MS/MS assay and dog pharmacokinetics of the dimeric pyrrolobenzodiazepine SJG-136 (NSC 694501).

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060807

Title: Time-dependent cytotoxicity induced by SJG-136 (NSC 694501): influence of the rate of interstrand cross-link formation on DNA damage signaling.

Journal: Molecular cancer therapeutics 20060601

Title: AACR-NCI-EORTC--17th symposium: Molecular targets and cancer therapeutics. 14-18th November 2005, Philadelphia, PA, USA.

Journal: IDrugs : the investigational drugs journal 20060101

Title: Direct liquid chromatography determination of the reactive imine SJG-136 (NSC 694501).

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050805

Title: Influence of P-glycoprotein expression on in vitro cytotoxicity and in vivo antitumour activity of the novel pyrrolobenzodiazepine dimer SJG-136.

Journal: European journal of cancer (Oxford, England : 1990) 20050801

Title: Sequence-selective interaction of the minor-groove interstrand cross-linking agent SJG-136 with naked and cellular DNA: footprinting and enzyme inhibition studies.

Journal: Biochemistry 20050322

Title: Synthesis of fluorinated analogues of SJG-136 and their DNA-binding potential.

Journal: Bioorganic & medicinal chemistry letters 20041115

Title: SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumor activity: part 1: cellular pharmacology, in vitro and initial in vivo antitumor activity.

Journal: Cancer research 20040915

Title: SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumor activity: part 2: efficacy evaluations.

Journal: Cancer research 20040915

Title: The novel sequence-specific DNA cross-linking agent SJG-136 (NSC 694501) has potent and selective in vitro cytotoxicity in human B-cell chronic lymphocytic leukemia cells with evidence of a p53-independent mechanism of cell kill.

Journal: Cancer research 20040915

Title: Preliminary pharmacokinetic and bioanalytical studies of SJG-136 (NSC 694501), a sequence-selective pyrrolobenzodiazepine dimer DNA-cross-linking agent.

Journal: Investigational new drugs 20040801

Title: Synthesis of the first example of a C2-C3/C2'-C3'-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepine dimer.

Journal: Bioorganic & medicinal chemistry letters 20011105

Title: Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity.

Journal: Journal of medicinal chemistry 20010301

Title: Gregson SJ, et al. Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity. J Med Chem. 2001 Mar 1;44(5):737-48.

Title: Mellinas-Gomez M, et al. Activity of the DNA minor groove cross-linking agent SG2000 (SJG-136) against canine tumours. BMC Vet Res. 2015 Aug 19;11:215.

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