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SJG-136

CAS No.:
232931-57-6
Catalog Number:
AG002MT1
Molecular Formula:
C31H32N4O6
Molecular Weight:
556.6090
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
98+%
1 week
United States
$424
- +
2mg
98+%
1 week
United States
$513
- +
Product Description
Catalog Number:
AG002MT1
Chemical Name:
SJG-136
CAS Number:
232931-57-6
Molecular Formula:
C31H32N4O6
Molecular Weight:
556.6090
MDL Number:
MFCD19443671
IUPAC Name:
(6aS)-3-[3-[[(6aS)-2-methoxy-8-methylidene-11-oxo-7,9-dihydro-6aH-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]propoxy]-2-methoxy-8-methylidene-7,9-dihydro-6aH-pyrrolo[2,1-c][1,4]benzodiazepin-11-one
InChI:
InChI=1S/C31H32N4O6/c1-18-8-20-14-32-24-12-28(26(38-3)10-22(24)30(36)34(20)16-18)40-6-5-7-41-29-13-25-23(11-27(29)39-4)31(37)35-17-19(2)9-21(35)15-33-25/h10-15,20-21H,1-2,5-9,16-17H2,3-4H3/t20-,21-/m0/s1
InChI Key:
RWZVMMQNDHPRQD-SFTDATJTSA-N
SMILES:
COc1cc2c(cc1OCCCOc1cc3N=C[C@H]4N(C(=O)c3cc1OC)CC(=C)C4)N=C[C@H]1N(C2=O)CC(=C)C1
UNII:
KT0ZQ64X1A
NSC Number:
694501
Properties
Complexity:
1020  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
556.232g/mol
Formal Charge:
0
Heavy Atom Count:
41  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
556.619g/mol
Monoisotopic Mass:
556.232g/mol
Rotatable Bond Count:
8  
Topological Polar Surface Area:
102A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.9  
Literature
Title Journal
Small molecule drugs - optimizing DNA damaging agent-based therapeutics. Current opinion in pharmacology 20120801
Pharmacokinetics, pharmacodynamics and metabolism of the dimeric pyrrolobenzodiazepine SJG-136 in rats. Cancer chemotherapy and pharmacology 20110901
Phase I pharmacokinetic and pharmacodynamic study of SJG-136, a novel DNA sequence selective minor groove cross-linking agent, in advanced solid tumors. Clinical cancer research : an official journal of the American Association for Cancer Research 20110601
The development of pyrrolobenzodiazepines as antitumour agents. Expert opinion on investigational drugs 20110601
A phase I trial of SJG-136 (NSC#694501) in advanced solid tumors. Cancer chemotherapy and pharmacology 20100401
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. Bioorganic & medicinal chemistry letters 20091115
The pyrrolobenzodiazepine dimer SJG-136 forms sequence-dependent intrastrand DNA cross-links and monoalkylated adducts in addition to interstrand cross-links. Journal of the American Chemical Society 20090930
Phase I study of sequence-selective minor groove DNA binding agent SJG-136 in patients with advanced solid tumors. Clinical cancer research : an official journal of the American Association for Cancer Research 20090315
Remarkable enhancement in the DNA-binding ability of C2-fluoro substituted pyrrolo[2,1-c][1,4]benzodiazepines and their anticancer potential. Bioorganic & medicinal chemistry 20090215
ABCB1 genetic polymorphism influences the pharmacology of the new pyrrolobenzodiazepine derivative SJG-136. The pharmacogenomics journal 20080801
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. Bioorganic & medicinal chemistry letters 20080315
An assay combining high-performance liquid chromatography and mass spectrometry to measure DNA interstrand cross-linking efficiency in oligonucleotides of varying sequences. Analytical biochemistry 20080301
Determination of chemically reduced pyrrolobenzodiazepine SJG-136 in human plasma by HPLC-MS/MS: application to an anticancer phase I dose escalation study. Journal of mass spectrometry : JMS 20080101
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. British journal of cancer 20070716
The hollow fibre model--facilitating anti-cancer pre-clinical pharmacodynamics and improving animal welfare. International journal of oncology 20061201
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). Bioorganic & medicinal chemistry letters 20061101
Design, synthesis, and biophysical and biological evaluation of a series of pyrrolobenzodiazepine-poly(N-methylpyrrole) conjugates. Journal of medicinal chemistry 20060907
LC-MS/MS assay and dog pharmacokinetics of the dimeric pyrrolobenzodiazepine SJG-136 (NSC 694501). Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060807
Time-dependent cytotoxicity induced by SJG-136 (NSC 694501): influence of the rate of interstrand cross-link formation on DNA damage signaling. Molecular cancer therapeutics 20060601
AACR-NCI-EORTC--17th symposium: Molecular targets and cancer therapeutics. 14-18th November 2005, Philadelphia, PA, USA. IDrugs : the investigational drugs journal 20060101
Direct liquid chromatography determination of the reactive imine SJG-136 (NSC 694501). Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050805
Influence of P-glycoprotein expression on in vitro cytotoxicity and in vivo antitumour activity of the novel pyrrolobenzodiazepine dimer SJG-136. European journal of cancer (Oxford, England : 1990) 20050801
Sequence-selective interaction of the minor-groove interstrand cross-linking agent SJG-136 with naked and cellular DNA: footprinting and enzyme inhibition studies. Biochemistry 20050322
Synthesis of fluorinated analogues of SJG-136 and their DNA-binding potential. Bioorganic & medicinal chemistry letters 20041115
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. Cancer research 20040915
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. Cancer research 20040915
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. Cancer research 20040915
Preliminary pharmacokinetic and bioanalytical studies of SJG-136 (NSC 694501), a sequence-selective pyrrolobenzodiazepine dimer DNA-cross-linking agent. Investigational new drugs 20040801
Synthesis of the first example of a C2-C3/C2'-C3'-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepine dimer. Bioorganic & medicinal chemistry letters 20011105
Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity. Journal of medicinal chemistry 20010301
Properties