DIAZEPINOMICIN


Synonyms	Amo-01 BU-4664L Diazepinomicin ECO-4601 TLN-4601
Status
Molecule Category	UNKNOWN
UNII	YPH994Y0RF
EPA CompTox	DTXSID40223539


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	SALVHVNECODMJP-GNUCVDFRSA-N
Smiles	CC(C)=CCC/C(C)=C/CC/C(C)=C/CN1C(=O)c2cccc(O)c2Nc2c(O)cc(O)cc21
InChI	InChI=1S/C28H34N2O4/c1-18(2)8-5-9-19(3)10-6-11-20(4)14-15-30-23-16-21(31)17-25(33)27(23)29-26-22(28(30)34)12-7-13-24(26)32/h7-8,10,12-14,16-17,29,31-33H,5-6,9,11,15H2,1-4H3/b19-10+,20-14+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C28H34N2O4
Molecular Weight	462.59
AlogP	6.93
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	8.0
Polar Surface Area	93.03
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	34.0

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

PubMed ID : 20056543

DOI : 10.1016/j.bmcl.2009.12.055

Year : 2010

Volume : 20

Issue : 3

First Page : 963

Last Page : 965

Authors : Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.

Abstract : In the screening for antitumor leads from microbial secondary metabolites, BU-4664L (1), a naturally occurring dibenzodiazepine, was found to inhibit tumor invasion and angiogenesis in vitro. Compound 1 inhibited the gelatinase activities of MMP-2 and MMP-9 and the cellular motility. Four derivatives (2-5) were synthesized from 1 and their antitumor activities were evaluated. Compounds 3 and 4 exhibited potent anti-angiogenic effects on HUVEC, together with remarkable inhibition of cell migration at nanomolar concentrations, and showed much lower cytotoxicity.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

PubMed ID : 20056543

DOI : 10.1016/j.bmcl.2009.12.055

Year : 2010

Volume : 20

Issue : 3

First Page : 963

Last Page : 965

Authors : Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

PubMed ID : 20056543

DOI : 10.1016/j.bmcl.2009.12.055

Year : 2010

Volume : 20

Issue : 3

First Page : 963

Last Page : 965

Authors : Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

PubMed ID : 20056543

DOI : 10.1016/j.bmcl.2009.12.055

Year : 2010

Volume : 20

Issue : 3

First Page : 963

Last Page : 965

Authors : Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

PubMed ID : 20056543

DOI : 10.1016/j.bmcl.2009.12.055

Year : 2010

Volume : 20

Issue : 3

First Page : 963

Last Page : 965

Authors : Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

PubMed ID : 20056543

DOI : 10.1016/j.bmcl.2009.12.055

Year : 2010

Volume : 20

Issue : 3

First Page : 963

Last Page : 965

Authors : Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

PubMed ID : 20056543

DOI : 10.1016/j.bmcl.2009.12.055

Year : 2010

Volume : 20

Issue : 3

First Page : 963

Last Page : 965

Authors : Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

PubMed ID : 20056543

DOI : 10.1016/j.bmcl.2009.12.055

Year : 2010

Volume : 20

Issue : 3

First Page : 963

Last Page : 965

Authors : Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

PubMed ID : 20056543

DOI : 10.1016/j.bmcl.2009.12.055

Year : 2010

Volume : 20

Issue : 3

First Page : 963

Last Page : 965

Authors : Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.

Reference

Journal : Bioorg. Med. Chem. Lett.

Title : Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives.

PubMed ID : 20056543

DOI : 10.1016/j.bmcl.2009.12.055

Year : 2010

Volume : 20

Issue : 3

First Page : 963

Last Page : 965

Authors : Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.

Assay Description	Organism	Bioactivity
Antiinvasive activity against mouse Colon 26-L5 by Matrigel assay	Mus musculus	1.0 ug.mL-1
Antiinvasive activity against mouse Renca by Matrigel assay	Mus musculus	0.78 ug.mL-1
Cytotoxicity against mouse Colon 26-L5 cells	Mus musculus	7.8 ug.mL-1
Cytotoxicity against mouse Renca cells	Mus musculus	8.3 ug.mL-1
Cytotoxicity against HUVEC cells	Homo sapiens	2.0 ug.mL-1
Antiinvasive activity against mouse Colon 26-L5 assessed as inhibition of cell migration after 6 hrs by Matrigel assay	Mus musculus	0.63 ug.mL-1
Antiangiogenic activity against HUVEC cells assessed as inhibition of vascular formation after 6 hrs by wound healing assay	Homo sapiens	0.72 ug.mL-1
Inhibition of MMP2	None	0.46 ug.mL-1
Inhibition of MMP9	None	0.6 ug.mL-1
Antiinvasive activity against HUVEC assessed as inhibition of cell migration after 6 hrs by Matrigel assay	Homo sapiens	0.43 ug.mL-1

Cross References

Resources	Reference
ChEBI	156321
ChEMBL	CHEMBL550961
DrugBank	DB12420
FDA SRS	YPH994Y0RF
PubChem	9868980
SureChEMBL	SCHEMBL1180715
ZINC	ZINC000003938687

CONTENTS

Structure
Chemical and Physical Properties