PRODIGIOSIN

PRODIGIOSIN 구조식 이미지
카스 번호:
82-89-3
상품명:
PRODIGIOSIN
동의어(영문):
Nsc47147;Aids010622;Aids-010622;PRODIGIOSIN;Prodigiosine;2-Methyl-3-amyl-6-methoxyprodigiosene;4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl], 2,2'bipyrrole;4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrol];4-Methoxy-5-(4-pentyl-5-methyl-2H-pyrrole-2-ylidenemethyl)-2,2'-bi[1H-pyrrole];4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrole]
CBNumber:
CB5156304
분자식:
C20H25N3O
포뮬러 무게:
323.43
MOL 파일:
82-89-3.mol
MSDS 파일:
SDS

PRODIGIOSIN 속성

녹는점
151-152°
끓는 점
554.3±50.0 °C(Predicted)
밀도
1.12±0.1 g/cm3(Predicted)
저장 조건
-20C
용해도
Acetonitrile: Soluble; Ethanol: Soluble; Methanol: Soluble
물리적 상태
진한 빨간색 고체
산도 계수 (pKa)
17.09±0.50(Predicted)
색상
진한 빨간색

안전

PRODIGIOSIN C화학적 특성, 용도, 생산

용도

Prodigiosin is an intensely red, pyrrole pigment produced by several bacteria, most notably Serratia marcescens. Prodigiosin has a broad biological profile with activity against fungi, tumour cell lines and malaria. It was shown to be an immunosuppressant in 2007. Prodigiosin acts via caspase inhibition to induce of apoptosis in human primary cancer cells. Prodigiosin also acts as an inducer of p21WAF1/CIP1 expression via transforming growth factor-β receptor pathway, and activates NAG-1 via glycogen synthase kinase-3β.

정의

ChEBI: A member of the class of tripyrroles that is a red-coloured pigment with antibiotic properties produced by Serratia marcescens.

일반 설명

A cell-permeable tripyrrole alkaloid compound that displays immunosuppressive and anti-tumor properties irrespective of p53 status and multidrug resistance. Shown to selectively upregulate p21WAF/CIP1 and NAG-1 (nonsteroidal anti-inflammatory drug-activated gene 1) and downregulate survivin expression levels, induce mitochondria-mediated apoptosis and cell cycle arrest in tumor cells. Prevents FADD phosphorylation (IC50 = 2.0 μM in A549-FKR cells) through inhibition of FADD-kinase CK1α (IC50 ~ 6.0 μM in SW620-BGCR cells) and augments cisplatin (Cat. No. 232120)-induced apoptosis. Blocks NF-κB activation by decreasing pIκBα (by 63% at 3 μM) and IκBα levels in A549 cells, and shrinks tumor growth in A549-FKR tumor xenograft mouse model (3 mg/kg, i.p., o.d.).

효소 저해제

This red bacterial pigment (FWfree-base = 323.44 g/mol; melting point = 151- 152°C) is an antibiotic produced by Serratia marcescens (formerly Chromobacterium prodigiosum). Prodigiosin is the parent member of a class of pyrrole-containing natural products that exhibit immunosuppressive, cytotoxic, and apoptotic activity and can facilitate copper-promoted oxidative double-strand DNA cleavage through reductive activation of Cu2+. They also uncouple lysosomal vacuolar-type ATPases by promoting H+/Cl– symport activity. The solid pigment is dark red and displays a green reflex. Acidic aqueous solutions are also red, but neutral or alkaline solutions are orange-yellow. Target(s): DNA topoisomerase I; DNA topoisomerase II; FoF1 ATPase, or H+-transporting two-sector ATPase, as an uncoupler; H+/K+-ATPase, as an uncoupler; proton translocation, as an uncoupler; and Serratia marcescens nuclease.

PRODIGIOSIN 준비 용품 및 원자재

원자재

준비 용품


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