CN105906642A - Rhodamine hydrazide derivative, and preparation method and application thereof - Google Patents

Rhodamine hydrazide derivative, and preparation method and application thereof Download PDF

Info

Publication number
CN105906642A
CN105906642A CN201610278567.4A CN201610278567A CN105906642A CN 105906642 A CN105906642 A CN 105906642A CN 201610278567 A CN201610278567 A CN 201610278567A CN 105906642 A CN105906642 A CN 105906642A
Authority
CN
China
Prior art keywords
acid
rhodamine
hydrazide derivatives
rhodamine hydrazide
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201610278567.4A
Other languages
Chinese (zh)
Inventor
邹祥
李虹庆
左华
李天夫
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Southwest University
Original Assignee
Southwest University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Southwest University filed Critical Southwest University
Priority to CN201610278567.4A priority Critical patent/CN105906642A/en
Publication of CN105906642A publication Critical patent/CN105906642A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Physics & Mathematics (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Biophysics (AREA)
  • Analytical Chemistry (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Materials Engineering (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

The invention discloses a rhodamine hydrazide derivative, and a preparation method and application thereof. The rhodamine hydrazide derivative is obtained through condensation reaction between rhodamine hydrazide and p-hydroxyacetophenone in an ethanol solution via Schiff base. The compound has a good linear relation with fluorescence intensity within the pH range of 2-5, thereby being capable of serving as a pH response fluorescence probe and being used for screening bacterial strains with high acid production capability, such as high-yield malic acid strains. The preparation method used for screening the high-yield bacterial strains has the advantages of high sensitivity, high accuracy, quickness, high throughput and the like.

Description

Rhodamine hydrazide derivatives and its preparation method and application
Technical field
The invention belongs to chemical field, be specifically related to a kind of rhodamine hydrazide derivatives, further relate to the system of rhodamine hydrazide derivatives Preparation Method and the application in pH response fluorescent probe.
Background technology
Polymalic acid (Polymalic acid, PMA) is by Aureobasidium pullulans (Aureobasidium pullulans) fermenting and producing A kind of novel high molecular polymer, is polymerized with L MALIC ACID in vivo for only monomer, and polymalic acid has the biology of height The compatibility, biological degradability and the advantage such as Bioabsorbable, safety non-toxic, lead at pharmaceutical carrier, organizational project, food etc. Territory tool has been widely used.
Currently, owing to polymalic acid bacterial strain acid producing ability is low, restrict its industrialized production always, therefore use screening through luring Become or the high yield polymalic acid bacterial strain of metabolic engineering is the task of top priority.(the poly-Fructus Mali pumilae of a kind of a large amount of generation is reported such as Qiao Changsheng etc. The mutagenic strain Aureobasidium pullulans TKPM00006 of acid and cultural method, granted patent 200910071018.X), containing By the polymalic acid superior strain of transparent circle size screening ultraviolet complex mutation on the solid plate of calcium carbonate, but the method is accurate Spending low, transparent circle is difficult to observe, and primary dcreening operation can cause a large amount of superior strain to be lost.Therefore, need badly a kind of sensitive and accuracy is high, Quickly, the probe of high flux screening high yield polymalic acid or method, for quickly, accurately screening is through physics, chemical method mutation Or the bacterial strain of metabolic engineering.
Summary of the invention
In view of this, during it is an object of the invention to avoid Screening of strain with high productivity random blindly, the technological deficiency such as workload is big, Synthesizing a kind of fluorescent probe sensitive in the range of pH value 2～5, concrete technical scheme is as follows:
Rhodamine hydrazide derivatives, double (the dimethylamino)-2-of chemical name: (E)-3', 6'-((sub-second of 1-(4-hydroxy phenyl) Base) amino) spiral shell [isoindoline-1,9'-ton]-3-ketone, its structure is as shown in formula I:
Present invention also offers the preparation method of rhodamine hydrazide derivatives, specific as follows: with rhodamine hydrazides and para hydroxybenzene second Ketone is raw material, using ethanol as solvent, obtains rhodamine hydrazide derivatives by Schiff's base condensation reaction.
Preferably, rhodamine hydrazides is dissolved in ethanol with parahydroxyacet-ophenone 1:4 in molar ratio, is heated to reflux 6～24h to sieve Red bright hydrazides reaction completely, then removes solvent, is dissolved in water, be then extracted with ethyl acetate, obtain rhodamine acyl through recrystallization Hydrazine derivate.
Utilize fluorescence intensity and the good linear relation of acid ph value response of the rhodamine hydrazide derivatives of synthesis, may be used for Preparation pH responds fluorescent probe, and this probe is for the test fluid that pH scope is 2～5 of response.The acid producing ability of bacterial strain is the strongest, PH value is the lowest, is therefore applicable to screen the bacterial strain that acid producing ability is strong, and producing acid can be that organic acid can also be for mineral acid, owing to having The pH scope of machine acid is 2～4, so being more suitable for producing the screening of organic acid bacterial strain, its organic acid is selected from malic acid, fumaric acid, fourth One or more in diacid, α-ketoglutaric acid, citric acid, gluconic acid.
The present invention is additionally operable to screen high yield polymalic acid bacterial strain, and the acid producing ability utilizing bacterial strain is the strongest, and pH value is the lowest, in deep-well plates In obtain mutant AH-21 by low for high flux screening pH bacterial strain, screening, find that bacterial strain low for pH gathers by fermentation checking Apple production is improved, and improves 13.8% than original starting strain polymalic acid fermentation yield, shows to utilize the present invention open Rhodamine hydrazide derivatives screening superior strain have sensitive height, accuracy high, quickly, the advantage such as high flux.
The original bacterium that sets out used in the present invention is for producing polymalic acid strain Aureobasidium pullulans CCTCC NO: M2012223, or derive from DSMZ of United States Department of Agriculture (USDA) (NRRL), American type culture collection (ATCC), The Culture Collection such as China General Microbiological culture presevation administrative center (CGMCC) or natural separation produce polymalic acid Aureobasidium belongs to or Physarum strain.
In the present invention, ARTP is atmospheric pressure at room plasma (Atmospheric and Room Temperature Plasma) Be called for short, it is possible under atmospheric pressure produce temperature between 25-40 DEG C, there is high activity particle (include being in the helium of excited state Atom, oxygen atom, nitrogen-atoms, OH free radical etc.) plasma jet of concentration.The present invention uses ARTP technology mutation Aureobasidium pullulans bacterial strain, concrete mutation parameter is: processes power 50-200W, helium gas jet amount 5-30SLM, processes distance 0-10 Mm, mutation time 10-120s.After dilution, it is spread evenly across on YPD flat board, produces mass mutation strain.
The beneficial effects of the present invention is: the present invention has synthesized new rhodamine hydrazide derivatives, and fluorescence intensity is at pH value 2-5 In the range of there is good linear relation, fluorescent probe can be responded as pH, owing to the acid producing ability of bacterial strain is the strongest, pH value is more Low, the acid producing ability of bacterial strain therefore can be indirectly reflected by rhodamine hydrazide derivatives fluorescence intensity.Sieve in conjunction with high flux Screening device, rapid screening can obtain the positive mutating strain of high yield.Utilize the screening technique that the present invention provides, compare traditional bromine cresol The screening techniques such as green variable color circle development process, screening accuracy increases substantially, and reduces workload, improves screening efficiency, tool There is good application prospect.
Accompanying drawing explanation
In order to make the purpose of the present invention, technical scheme and beneficial effect clearer, the present invention provides drawings described below:
Fig. 1 is the synthetic route chart of fluorescent probe L.
Fig. 2 is probe L fluorescence intensity and pH value response relation.
Fig. 3 is fluorescence intensity and the pH value result of variations (λ ex=563nm) of fractional mutations strain.
Fig. 4 is that (zero represents the starting strain poly-Herba Marsileae Quadrifoliae of CCTCC M2012223 to 5L fermentation tank mutant AH-21 fermentation the result Fruit acid content；● represent mutant AH-21 polymalic acid yield；△ represents that starting strain CCTCC M2012223 thalline is raw Thing amount；▲ represent mutant AH-21 Fungal biodiversity；Represents starting strain CCTCC M2012223 concentration of glucose； ■ represents mutant AH-21 concentration of glucose).
Detailed description of the invention
Below in conjunction with accompanying drawing, the preferred embodiments of the present invention are described in detail.Unreceipted actual conditions in embodiment Experimental technique, generally according to normal condition or according to the condition proposed by manufacturer.
Embodiment 1, the synthesis of rhodamine hydrazide derivatives fluorescent probe
The synthesis of rhodamine hydrazide derivatives fluorescent probe, comprises the steps:
(1) synthesis of rhodamine hydrazides: take 1.5g rhodamine B and be dissolved in 100mL ethanol, room temperature (18～25 DEG C) stirs Dropping 5mL mass fraction is the hydrazine hydrate of 80%；It is heated to reflux 12～48h, then reactant liquor is concentrated into reactant liquor cumulative volume 1/8th, stand overnight；Next day sucking filtration white precipitate, drying, collect obtain rhodamine hydrazides；
(2) rhodamine hydrazides 0.168g (0.37mmol) and the parahydroxyacet-ophenone 0.201g (1.48mmol) of step (1) gained are taken It is dissolved in 10～100mL ethanol, is heated to reflux 6～24h to rhodamine hydrazides reaction (TLC detection rhodamine hydrazides reaction completely The most complete), add heat extraction solvent the most under vacuum conditions, after adding 5～50mL water, enter by 20～100mL ethyl acetate Row extraction, is recrystallized to give rhodamine hydrazide derivatives fluorescent probe from ethyl acetate after extracting three times, chemistry is entitled: (E) Double (dimethylamino)-2-((1-(4-hydroxy phenyl) ethylidene) amino) spiral shell [isoindoline-1,9'-the ton]-3-of-3', 6'- Ketone, referred to as probe L, overall reaction route such as Fig. 1.
The present embodiment is recrystallized to give probe L 0.142g, and productivity is 84.5%.
With DMSO as solvent, compound concentration is the probe L solution of 50 μMs, then pH value be 1.82,2.25,2.98, 3.52, in the buffer of 4.07,4.65,5.47 and 6.23, it is respectively 563nm and 580nm with excitation wavelength and transmitting wavelength Detection fluorescent probe L fluorescence intensity (v/v=1:1) under condition of different pH, result is as shown in Figure 2.Result shows, synthesis Probe L at pH in the range of 2～5, there is the good range of linearity (R2=0.9951), can be as pH value at 2～5 models Enclose interior pH and respond fluorescent probe.The strongest owing to producing the acid producing ability of acids bacterial strain, pH value is the lowest, thus can pass through fluorescence Intensity indirectly reflects the acid producing ability of bacterial strain, in conjunction with high flux screening device (deep-well plates), rapid screening can obtain Producing Strain Strain.Owing to organic acid belongs to weak acid, pH value is generally in the range of 2～4, and it is organic that the probe L therefore synthesized is particularly well-suited to high yield Acid bacterial strain screening, such as the bacterial strain of malic acid, fumaric acid, succinic acid, α-ketoglutaric acid, citric acid, gluconic acid etc..
Embodiment 2, utilize probe L screen high yield polymalic acid bacterial strain
First, polymalic acid bacterial strain mutation library is built:with Aureobasidium pullulans (A.pullulans) CCTCC M2012223 for going out Sending out bacterial strain, after shake-flask culture 48h, bead is smashed and is prepared single cell suspension, uses atmospheric pressure at room plasma (Atmospheric And Room Temperature Plasma, ARTP) technology mutagenic strain, concrete mutation parameter is:process power 120W, Helium gas jet amount 10SLM, processes distance 2mm, mutation time 50s; After dilution, evenly coat on YPD flat board, produce Raw mass mutation strain.
Then, utilize probe L screening high yield polymalic acid bacterial strain, mutant strains all ARPT is inoculated in to the seed containing 2mL in 48 hole depth orifice plates of culture medium, cultivate after 48h for 25 DEG C, then get 200 μ L seed liquor culture transferrings to containing 2mL fermentation medium 48 hole depth orifice plates in to cultivate 48h. deep-well plates centrifugal, get 100 μ L supernatants to 96 orifice plates, then adding solvent is DMSA, concentration is that the 100 μ L probe L solution of 50 μ M mix, utilize multi-functional ELIASA (Tecan Infinite 200PRO), ? excitation wavelength and emission wavelength are respectively 563nm and 580nm detects its fluorescence intensity, the fluorescence intensity of part bacterial strain is as Fig. 3 shown in. result shows, AH-21 fluorescence intensity is the highest, pH value is minimum, the polymalic acid output of predicting this bacterial strain is the highest.
In the present embodiment, described seed culture medium is glucose 60g/L, KH2PO4 0.05g/L、NH4NO3 2g/L、ZnSO4 0.05 g/L、MgSO40.05g/L, corn steep liquor 1g/L and CaCO3 20g/L。
Embodiment 3, fermentation checking
Adopt 5L fermentation tank technique, fermentating formula is glucose 90g/L, ammonium chloride 2g/L, KH2PO4 0.2g/L、ZnSO4 0.15 g/L、MgSO40.2g/L, at fermentation tank ventilation ratio (1:1, v/v) more than, speed of agitator 400～700rpm, by mutant strain it is 76 hours that AH-21 and original starting strain CCTCC M2012223 carry out fermented incubation time, then detect polymalic acid output, result is as shown in Figure 4. and result shows, mutant strain AH-21 produces polymalic acid 42g/L, than starting strain CCTCC M2012223 has improved 13.8%. result and has shown, the superior strain screening by fluorescence probe is polymalic acid output after fermentation also be improved, therefore can be by utilizing probe L can screen and obtain high yield polymalic acid as pH response fluorescence probe bacterial strain.
Finally explanation is, above preferred embodiment is only unrestricted in order to technical scheme of the present invention to be described, although the present invention is described in detail by above preferred embodiment, but those skilled in the art are to be understood that, can make various changes to it in the form and details, and not depart from the claims in the present invention book limited range.

Claims (9)

1. rhodamine hydrazide derivatives, is characterized in that: its structure is suc as formula shown in I:
2. the preparation method of rhodamine hydrazide derivatives described in claim 1, is characterized in that: taking rhodamine hydrazides and parahydroxyacet-ophenone as raw material, using ethanol as solvent, obtain rhodamine hydrazide derivatives by schiff bases condensation reaction.
3. the preparation method of rhodamine hydrazide derivatives according to claim 2, it is characterized in that, by rhodamine hydrazides and parahydroxyacet-ophenone in molar ratio 1:4 be dissolved in ethanol, adding hot reflux 6～24h reacts completely to rhodamine hydrazides, then except desolventizing, be dissolved in water, be then extracted with ethyl acetate, through the rhodamine hydrazide derivatives that is recrystallized to obtain.
4. the application of rhodamine hydrazide derivatives in preparation pH response fluorescence probe described in claim 1.
5. application according to claim 4, is characterized in that: the pH scope of described pH response fluorescence probe response is 2～5.
6. described in claim 1, rhodamine hydrazide derivatives screens the strong bacterial strain of acid producing ability as pH response fluorescence probe.
7. application according to claim 6, is characterized in that: described acid is organic acid.
8. application according to claim 7, is characterized in that: described organic acid is malic acid, fumaric acid, succinic acid, KG, citric acid, gluconic acid.
9. described in claim 1, rhodamine hydrazide derivatives screens the application in high yield polymalic acid bacterial strain as pH response fluorescence probe.
CN201610278567.4A 2016-04-28 2016-04-28 Rhodamine hydrazide derivative, and preparation method and application thereof Pending CN105906642A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610278567.4A CN105906642A (en) 2016-04-28 2016-04-28 Rhodamine hydrazide derivative, and preparation method and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610278567.4A CN105906642A (en) 2016-04-28 2016-04-28 Rhodamine hydrazide derivative, and preparation method and application thereof

Publications (1)

Publication Number Publication Date
CN105906642A true CN105906642A (en) 2016-08-31

Family

ID=56752101

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610278567.4A Pending CN105906642A (en) 2016-04-28 2016-04-28 Rhodamine hydrazide derivative, and preparation method and application thereof

Country Status (1)

Country Link
CN (1) CN105906642A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115308186A (en) * 2022-10-12 2022-11-08 广州市乾相生物科技有限公司 fluorescence-pH biosensor and preparation method and application thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103232465A (en) * 2013-04-11 2013-08-07 天津师范大学 A preparation method and applications of a Schiff base compound of benzophenone rhodamine 6G hydrazide
CN103232466A (en) * 2013-04-11 2013-08-07 天津师范大学 Preparation method of compound (I) 4-hydroxy substituted phenyl imine type rhodamine 6G fluorescence molecule probe and purpose thereof
CN103242327A (en) * 2013-04-11 2013-08-14 天津师范大学 P-N-methyl cyclopentaldehyde rhodamine 6G pH fluorescence molecular probe as well as preparation method and use thereof
CN103242330A (en) * 2013-04-11 2013-08-14 天津师范大学 Phenylimidogenrhodamine 6G hydrogen ion probe compound as well as preparation method and application thereof
CN103242331A (en) * 2013-04-11 2013-08-14 天津师范大学 Rhodamine 6GpH fluorescent molecular probe containing biphenyl group as well as preparation method and application thereof
CN104017568A (en) * 2014-05-23 2014-09-03 苏州科技学院 Rhodamine-containing Hg<2+> and pH bifunctional fluorescent probe and synthetic method

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103232465A (en) * 2013-04-11 2013-08-07 天津师范大学 A preparation method and applications of a Schiff base compound of benzophenone rhodamine 6G hydrazide
CN103232466A (en) * 2013-04-11 2013-08-07 天津师范大学 Preparation method of compound (I) 4-hydroxy substituted phenyl imine type rhodamine 6G fluorescence molecule probe and purpose thereof
CN103242327A (en) * 2013-04-11 2013-08-14 天津师范大学 P-N-methyl cyclopentaldehyde rhodamine 6G pH fluorescence molecular probe as well as preparation method and use thereof
CN103242330A (en) * 2013-04-11 2013-08-14 天津师范大学 Phenylimidogenrhodamine 6G hydrogen ion probe compound as well as preparation method and application thereof
CN103242331A (en) * 2013-04-11 2013-08-14 天津师范大学 Rhodamine 6GpH fluorescent molecular probe containing biphenyl group as well as preparation method and application thereof
CN104017568A (en) * 2014-05-23 2014-09-03 苏州科技学院 Rhodamine-containing Hg<2+> and pH bifunctional fluorescent probe and synthetic method

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115308186A (en) * 2022-10-12 2022-11-08 广州市乾相生物科技有限公司 fluorescence-pH biosensor and preparation method and application thereof
CN115308186B (en) * 2022-10-12 2023-01-17 广州市乾相生物科技有限公司 fluorescence-pH biosensor and preparation method and application thereof

Similar Documents

Publication Publication Date Title
Samorski et al. Quasi‐continuous combined scattered light and fluorescence measurements: A novel measurement technique for shaken microtiter plates
Saleski et al. Syntrophic co-culture amplification of production phenotype for high-throughput screening of microbial strain libraries
George et al. Comparison of the Baker's yeast process performance in laboratory and production scale
CN107475172B (en) Method for obtaining Geobacillus stearothermophilus spores
Zhang et al. Genome shuffling of the nonconventional yeast Pichia anomala for improved sugar alcohol production
CN105586033A (en) Rhodamine pH fluorescent probe containing glutamic acid structure and application of fluorescent probe
CN105906642A (en) Rhodamine hydrazide derivative, and preparation method and application thereof
Zheng et al. A temperature-shift strategy in batch microbial transglutaminase fermentation
CN103725669A (en) High-throughput screening method for high-yield monascus pigment strain
CN113528404A (en) Method for improving yield of bacillomycin D based on segmented fermentation of corn straw enzymatic hydrolysate base material
RU2409659C2 (en) Method of preparing liquid koji
Li et al. A novel rhodamine-based fluorescent pH probe for high-throughput screening of high-yield polymalic acid strains from random mutant libraries
CN105646552A (en) Zn(II) complex based on 5-hydroxynictinic acid and preparation method and application thereof
Li et al. Combining genetically encoded biosensors with droplet microfluidic system for enhanced glutaminase production by Bacillus amyloliquefaciens
CN105483171B (en) A kind of raising ubiquinone10The production method of industrial output
CN102352317B (en) Micro-culture method of pleuromutilin producing bacteria and high-throughput screening method of high-yield bacteria of pleuromutilin
CN110157770A (en) A kind of method of the high oil-producing schizochytrium limacinum mutant of high flux screening
CN109342415A (en) A kind of method of high-throughput detection eriodictyol
CN106047734B (en) The preparation method and application of bacterium source are strengthened in wine brewing
Shichang et al. Mutation-screening in L-(+)-lactic acid producing strains by ion implantation
Jansen et al. Microbioreactor‐assisted cultivation workflows for time‐efficient phenotyping of protein producing Aspergillus niger in batch and fed‐batch mode
CN105503938B (en) Pb (II) complexs and its synthetic method based on 5 bromo-nicotinic acids
CN109580604A (en) A kind of method of high-throughput detection naringenin
CN103911333A (en) High-yield phenylalanine production strain and method for producing phenylalanine by strain
Hanly et al. Validation and optimization of a yeast dynamic flux balance model using a parallel bioreactor system

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20160831