Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
5-Bromouracil
5-bromopyrimidine-2,4(1H,3H)-dione · BROMOURACIL · 5-BROMOPYRIMIDINE-2,4-DIOL · 5-BROMO-1H-PYRIMIDINE-2,4-DIONE · 5-Bromo-1,2,3,4-tetrahydropyrimidine-2,4-dione · 5-BrUra · 5-Bromuracil · 5-BROMOURACIL
식별자 및 물리적 특성
| CAS No. | 51-20-7 |
|---|---|
| 분자식 | C4H3BrN2O2 |
| 평균 분자량 | 190.98 g/mol |
| 단동위원소 질량 | 189.93778944 g/mol |
| SMILES | O=c1[nH]cc(Br)c(=O)[nH]1 |
| InChIKey | LQLQRFGHAALLLE-UHFFFAOYSA-N |
| PubChem CID | 5802 |
| ChEMBL | CHEMBL144730 |
| ChEBI | CHEBI:20552 |
| EC No. | 200-084-0 |
| DTXSID | DTXSID2058758 |
화학 및 물리적 성질
| XLogP | -0.2 |
|---|---|
| 극성 표면적 | 58.2 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 9 |
| 형식 전하 | 0 |
| 복잡도 | 199 |
| 물질 분류 | Biological Agents -> Nucleic Acids and Derivatives |
| SpringerMaterials Properties | Chemical shift |
| LogP(분배 계수) | log Kow = -0.21 |
| Color/Form | Prisms from water |
| 용해도 | less than 1 mg/mL at 75 °F (NTP, 1992)In water, 815 mg/L, temp not specified<1g/L |
| Decomposition | When heated to decomposition it emits very toxic fumes of /hydrogen bromide and nitrogen oxide/. |
| 녹는점 | 590 °F (NTP, 1992)310 °C>300 °C (lit.) |
| 증기압 | 0.00000023 [mmHg] |
| Physical Description | 5-bromouracil is a white powder. (NTP, 1992)Solid[Merck Index] White to off-white powder[Acros Organics MSDS] |
| 밀도 | 1.8710 (rough estimate) |
| 굴절률 | 1.6200 (estimate) |
| 저장 조건 | Keep in dark place,Sealed in dry,Room Temperature |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | 6.77±0.10(Predicted) |
| 색상 | 하얀색 |
| 용해도 | 냉수에 용해됨 |
| Merck | 14,1445 |
| BRN | 127176 |
| InChI | 1S/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) |
| InChIKey | LQLQRFGHAALLLE-UHFFFAOYSA-N |
| SMILES | BrC1=CNC(=O)NC1=O |
| NIST | 5-Bromouracil(51-20-7) |
| EPA | 5-Bromouracil (51-20-7) |
화학적 성질
Prisms from H 2 O.
안전 및 규제
| GHS 분류 | WarningH302 (90.7%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 43 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| 규제 정보 | 2,4(1H,3H)-Pyrimidinedione, 5-bromo-: Does not have an individual approval but may be used under an appropriate group standard |
| 운송 라벨(DOT) | Poison |
| 화재 위험 | Flash point data for this chemical are not available, but it is probably combustible. (NTP, 1992) |
| 건강 유해성 | ACUTE/CHRONIC HAZARDS: When heated to decomposition this chemical emits very toxic fumes of bromide ion and NOx. (NTP, 1992) |
| 유해성 요약 | Causes somnolence, muscle weakness, and dyspnea in intraperitoneal lethal-dose studies of mice (LD50 = 1,400 mg/kg)[RTECS] May cause irritationHarmful by ingestionRisk of irreversible adverse health effects[Acros Organics MSDS] See Uracil. |
| 반응성 그룹 | Amides and Imides |
| Reactivity Profile | A halogenated amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (90.7%) |
| 소화 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| 응급 처치 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| 비화재 누출 대응 | SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| 처리 방법 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Personal Protective Equipment (PPE) | MINIMUM PROTECTIVE CLOTHING: If Tyvek protective clothing is not worn during the handling of this chemical, wear disposable Tyvek sleeves taped to your gloves. |
| Treatment | EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. |
| 상호 작용 | The presence of 5-bromouracil (BU) as well as 5-bromo-2-deoxyuridine (BUdR) in the cultivation media of bacteria results in the distinct increase of UV sensitivity. With the nucleic acid base analogue 8-azaadenine (8-AA) a similar effect was confirmed, however, not so pronounced. In the experiments reported here the combined action of BU or BUdR and 8-AA on Escherichia coli, Proteus mirabilis, Bacillus subtilis and Bacillus cereus was investigated. The sensitization effect of BUdR does not increase if 8-AA is present additionally during cultivation. On the contrary, a decrease of sensibilization occurs. This result may be caused by the protective effect of the adenine derivative against UV irradiation, if it is present in the cell, but not incorporated into the DNA.The damages induced in E. coli AB2487 recA by Cerenkov emission and ionizing radiation contribute in an additive fashion to the overall lethality, and do not interact in a synergistic fashion. Bromouracil substitution enhances the lethal action of high energy X-irradiation on E. coli AB2487 recA by a mechanism involving enhanced radiosensitivity and enhanced photosensitivity. |
| 건강 영향 | 5-bromouracil is a mutagen (causes mutations) and a carcinogen. It can cause respiratory tract irritation if inhaled, skin irritation if it contacts the skin and eye irritation if it contacts the eyes. |
| 노출 경로 | Oral (L626)inhalation (L626)dermal (L626) |
| 독성 요약 | Thymidine phosphorylase, a pyrimidine salvage enzyme, transforms 5-bromouracil to 5-bromodeoxyuridine, a mutagenic analogue of thymidine. Ultimately, 5-bromouracil acts on DNA. It induces a random DNA point mutation via base substitution. The base pair will change from an A-T to a G-C or from a G-C to an A-T after a number of replication cycles, depending on whether 5-BrU is within the DNA molecule or is an incoming base when it is enolized or ionized. 5-Bromouracil normally pairs with adenine. However, the proportion of 5-bromouracil in the enol tautomer is higher than that of thymine because the bromine atom is more electronegative than is a methyl group on the C-5 atom. Thus, the incorporation of 5-bromouracil is especially likely to cause altered base-pairing in a subsequent round of DNA replication. |
| Signs and Symptoms | 5-bromouracil can cause hypermotility, diarrhea, weight loss and possibly death if large amounts are repeatedly ingested. |
| Environmental Biodegradation | ANAEROBIC: Bromouracil was reductively dehalogenated to stochiometric amounts of uracil when incubated 14 months in anoxic aquifer slurries containing 50 g sediment and 75 mL ground water(1). |
| Carcinogen Classification | Not listed by IARC. May cause heritable genetic damage. |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ... the effect of dietary pyrimidine analogs on growth and survival of Drosophila melanogaster was determined. One pair of male and female, 8-hours-old, newly hatched, wild type Drosophila melanogaster adults were transferred to a vial containing food supplemented with thymine, 5-bromouracil, uracil, orotic acid, cytosine, or uridine monophosphate at 0.13% of diet. Flies grown without supplement served as controls. Flies were allowed to mate and lay eggs. One week later, the parental flies were removed, eggs were allowed to hatch and after metamorphosis through larval, and pupal stages at 25 degrees C. Newly hatched adults were counted. The number of adult flies that hatched on each supplemented diet compared with the number that hatched on the control diet was used to calculate toxicity. The pyrimidines used in this experiment were ranked as follows: thymine greater than 5-bromouracil greater than uracil greater than orotic acid greater than cytosine greater than uridine monophosphate in decreasing order of toxicity. Correlating pyrimidine structure with toxicity to wild type Drosophila melanogaster, the data suggest that the toxicity was associated with the presence of a methyl or bromide group attached to carbon #5 of the pyrimidine ring. The presence of a ribose-phosphate group at nitrogen #1 on the pyrimidine ring alleviated pyrimidine toxicity./ALTERNATIVE and IN VITRO TESTS/ Substitution of thymine with 5-bromouracil in DNA is known to change interaction between DNA and proteins, thereby inducing various biological phenomena. /The authors/ hypothesize that A/T-rich scaffold/nuclear matrix attachment region (S/MAR) sequences are involved in the effects of 5-bromodeoxyuridine. /They/ examined an interaction between DNA containing an intronic S/MAR sequence of the immunoglobulin heavy chain gene and nuclear halos prepared from HeLa cells. Upon substitution with 5-bromouracil, the S/MAR DNA bound more tightly to the nuclear halos. The multi-functional nuclear matrix protein YY1 was also found to bind more strongly to 5-bromouracil-substituted DNA containing its recognition motif. These results are consistent with the above hypothesis./ALTERNATIVE and IN VITRO TESTS/ The miscoding properties of a 5-bromodeoxyuridine (dB) containing DNA template during in vitro replication have been investigated. 5-bromodeoxyuridine was introduced site-specifically into the amber 16 codon of a 25-mer oligodeoxynucleotide representing part of the sequence of phi x174am16(+)DNA. The dB containing oligodeoxynucleotide served as a template for in vitro replication by DNA polymerase alpha, DNA polymerase I (Escherichia coli) and AMV reverse transcriptase. The amber 16 revertant assay was used to detect the presence of misincorporated bases in the replication products. For all three DNA polymerases, the presence of dB does not constitute a significant barrier to replication. Errors at the position of dB substitution were found to originate exclusively from dGTP:dB mispairing during in vitro replication thus inducing A-T----G-C transitions. The dGTP:dB mismatches are formed at a 2-4-fold higher frequency as compared to dGTP:T mismatches. Our results indicate that the miscoding potential of dB-substituted DNA templates during replication is only weak at the specific site observed./ALTERNATIVE and IN VITRO TESTS/ /The authors/ synthesized and studied by proton NMR a duplex heptaoligonucleotide containing a 5-bromouracil (brU)-adenine base pair. This represents the first structural characterization of a B-form DNA containing brU. The brU.A base pair is Watson-Crick rather than Hoogsteen as seen for the monomers in the crystalline state. From analysis of the NOESY spectra at very short mixing times evidence is presented that substitution of brU for T induces significant conformational changes from that of a normal B DNA. The helix twist between brU4.A11 and G3.C12 is ca. 15 degrees and for both brU4 and G3 the glycosyl torsion angles are significantly changed. The imino proton of the bru.A base pair shows a pH insensitive line with which shows that the pK of brU in this base pair is very much higher than that of the monomer.For more Non-Human Toxicity Excerpts (Complete) data for BROMOURACIL (23 total), please visit the HSDB record page. |
| Toxicity Data | LD50: 1700 mg/kg (Rat, Intraperitoneal)LD50 1400 mg/kg (Mouse, Intraperitoneal) (T14) |
| Non-Human Toxicity Values | LD50 Mouse ip 1400 mg/kgLD50 Rat ip 1700 mg/kg |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | YQ9060000 |
| 관세 코드 | 29335995 |
| 위험 문구(R) | 22-46 |
| 위험 표시 | Xn |
| 안전 문구(S) | 36/37-53-45-24/25 |
| 저장 분류 | 11 - Combustible Solids |
| 유해 물질 데이터 | 51-20-7(Hazardous Substances Data) |
용도
개요
5-bromouracil (5-BU) is a uracil derivative, and its 5' position of the pyrimidine ring is halogenated. If 5-BU is incorporated into DNA in place of thymine, the tautomeric shift will occur, and the 5-BU will base pair with guanine. After the replication, an A-T to G-C transition occurs. Furthermore, the presence of 5-BU within DNA increases the sensitivity of the molecule to UV light. 5-BU is structurally similar to thymine. Therefore, it is considered a thymine analog and base-pairs normally with adenine. It is rarely present in its enol form, where its base pairs with guanine. 5-Bromouracil treats neoplasms in the form of its nucleoside, 5-bromo-2-deoxy-uridine[1-2].
용도
A major chemical mutagen. Incorporates into DNA, altering base-pair sequencing by replacing thymine
일반 설명
White powder.