Chromomycin a3 色霉素A3

CAS 7059-24-7 MFCD00043151

化学结构图

7059-24-7
SMILES: CO[C@H]1[C@@H](O)CC(O[C@H]2CC(Oc3cc4cc5c(c(O)c4c(O)c3C)C(=O)[C@@H](OC3C[C@@H](OC4C[C@H](OC6C[C@](C)(O)[C@@H](OC(C)=O)[C@H](C)O6)[C@@H](O)[C@H](C)O4)[C@H](O)[C@@H](C)O3)[C@H]([C@@H](OC)C(=O)[C@@H](O)[C@H](C)O)C5)O[C@@H](C)[C@H]2OC(C)=O)O[C@H]1C

化学属性

Mol. FormulaC57
Mol. Weight1183
TSCANo
Melting Point185° dec.
SolubilitySoluble in ethanol, DMSO, and ethyl acetate (10 mg/ml)
Stability对光线敏感

别名和识别编码

Chemical NameChromomycin A3
MDL NumberMFCD00043151
CAS Number7059-24-7
PubChem Substance ID656673
EC Number230-348-0
Synonym Aburamycin B Antibiotic 69895 A Antibiotic B 599 Chromomycin A(sub 3) Chromomycin A3 Chromomycin A3 from Streptomyces griseus NSC-58514 Olivomycin D, Toyomicin Toyomycin
Merck Number14,2238
Chemical Name Translation色霉素A3
Wiswesser Line NotationL C666 DVT&&J BQ FYO1&VYQYQ1 M1 NQ LO- BT6OTJ DOV1 F1EO- BT6OTJ DQ EO1 F1&& EO- BT6OTJ EQ F1
LabNetwork Molecule IDLN02124524
InChIInChI=1S/C57H82O26/c1-21-34(79-40-19-37(53(26(6)75-40)77-28(8)59)82-38-16-33(61)52(70-11)25(5)74-38)15-31-13-30-14-32(54(71-12)51(68)46(63)22(2)58)55(50(67)44(30)49(66)43(31)45(21)62)83-41-18-35(47(64)24(4)73-41)80-39-17-36(48(65)23(3)72-39)81-42-20-57(10,69)56(27(7)76-42)78-29(9)60/h13,15,22-27,32-33,35-42,46-48,52-56,58,61-66,69H,14,16-20H2,1-12H3/t22-,23-,24-,25-,26-,27+,32+,33-,35-,36-,37-,38-,39+,40+,41+,42+,46+,47-,48-,52+,53+,54+,55+,56+,57+/m1/s1
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分类

  • {SNA} Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Antiviral, Aureolic Acids, Bioactive Small Molecules, C-CH, Cell Biology, Chemical Structure Class, Interferes with DNA Synthesis, Mechanism of Action, Spectrum of Activity
  • {SNA} Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Apoptosis Detection, Apoptosis and Cell Cycle, Aureolic Acids, Bioactive Small Molecule Alphabetical Index, C-CH, Chemical Structure Class,

产品应用

  • Membrane-impermeant G/C-specific fluorescent DNA-binding dye.
  • Antibacterial antibiotic.
  • Antitumor antibiotic that inhibits RNA synthesis, especially in solid tumors.

安全信息

WGK Germany3
GHS Symbol
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前,切勿操作。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P301+P310
  • P308+P313
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P330 Rinse mouth. 漱口
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H300 Fatal if swallowed 吞食致命
  • H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
RTECSGB7875000
Signal word Danger
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
Hazard Codes T+
Safety Statements
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后,立即用大量…(由生产厂家指定)冲洗;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S53 Avoid exposure - obtain special instructions before use 避免接触,使用前获得特别指示说明;
Risk Statements
  • R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
  • R28 Very toxic if swallowed 吞咽极毒
Packing GroupI
UN Number UN3462
Storage condition 储存温度2-8℃
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 250 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al.,
   eds., Washington, DC, American Soc. for Microbiology, 1978
   Volume(issue)/page/year: 2,1401,1978

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Primate - monkey
DOSE/DURATION           : 330 ug/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - coma
   Gastrointestinal - hypermotility, diarrhea
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   27,259,1974

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Mammal - species unspecified
DOSE/DURATION           : 250 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al.,
   eds., Washington, DC, American Soc. for Microbiology, 1978
   Volume(issue)/page/year: 2,1401,1978

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1431 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NCISP* National Cancer Institute Screening Program Data Summary,
   Developmental Therapeutics Program. (Bethesda, MD 20205)
   Volum

TYPE OF TEST            : LDLo - Lowest published lethal

TYPE OF TEST            : DNA adduct
TEST SYSTEM             : Human Fibroblast
DOSE/DURATION           : 1 umol/L
REFERENCE :
   JJIND8 JNCI, Journal of the National Cancer Institute.  (Washington, DC)
   V.61-79, 1978-87. For publisher information, see JNCIEQ.
   Volume(issue)/page/year: 77,649,1986

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 4 mg/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   45,2813,1985

TYPE OF TEST            : DNA repair
TEST SYSTEM             : Bacteria - Bacillus subtilis
DOSE/DURATION           : 800 ng/plate
REFERENCE :
   TAKHAA Takeda Kenkyusho Ho.  Journal of the Takeda Research Laboratories.
   (Takeda Yakuhin Kogyo K.K., 2-17-85 Jusohon-machi, Y

TYPE OF TEST            : DNA adduct
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 2 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 89,95,1981

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 125 ug/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   45,2813,1985

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 100 ug/L
REFERENCE :
   NNBYA7 Nature (London), New Biology.  (Basingstoke, Hants., UK)  V.229-246,
   1971-73.  For publisher information, see NATUAS.  Volume(issue)/page/year:
   232,143,1971

TYPE OF TEST            : Cytogenetic analysis

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 250 ug/kg
SEX/DURATION            : male 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
REFERENCE :
   HIKYAJ Hinyokika Kiyo.  Journal of Urology.   (Kyoto Daigaku Igakubu,
   Hinyokikagaku Kyoshitsu, 54 Kawara-machi, Shogain, Sakyo-ku, Kyoto 606,
   Japan)  V.1-    1955-  Volume(issue)/page/year: 12,1339,1966

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 500 ug/kg
SEX/DURATION            : male 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
   JJPAAZ Japanese Journal of Pharmacology.  (Japanese Pharmacological Soc.,
   c/o Dept. of Pharmacology, Faculty of Medicine, Kyoto Univ., Sakyo-ku, Kyoto
   606, Japan)  V.1-    1951-  Volume(issue)/page/year: 10,64,1960

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 125 ug/kg
SEX/DURATION            : female 6-10 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured
   before birth)
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Specific Developmental Abnormalities - eye/ear
REFERENCE :
   OSDIAF Osaka Shiritsu Daigaku Igaku Zasshi.  Journal of the Osaka City
   Medical Center.  (Osaka, Japan)  V.4-23, 1955-74.  For publisher
   information, see OIGZDE.  Volume(issue)/page/year: 14,107,1965

其他信息

  • Chromomycin A3 : glycosidic antibiotic.
  • Chromomycin A3, a fluorescent DNA stain and antibiotic, has been reported to strongly inhibit zinc-dependent transcriptional activity of sheep Metallothionein 1A promoter in reporter gene assays of transfected cells. This compound has also been shown to be a potent inhibitor of neuronal apoptosis induced by glutathione depletion-induced oxidative stress and DNA-damaging agent Camptothecin. Mechanistic studies suggest that Chromomycin A3 antagonizes enhanced DNA binding of the transcription factors Sp1 and Sp3 to their cognate "G-C" box, induced by oxidative stress or DNA damage. Furthermore, by inhibiting transcription, Chromomycin A3 and its structural analogs can inhibit protein biosynthesis.

系列性分类


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