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Article(id=1195687995748696977, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1195707415279747621, articleNumber=1001-2494(2024)03-0263-07, orderNo=null, doi=10.11669/cpj.2024.03.010, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1686499200000, receivedDateStr=2023-06-12, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1763003832995, onlineDateStr=2025-11-13, pubDate=1707321600000, pubDateStr=2024-02-08, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1763008463737, onlineIssueDateStr=2025-11-13, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=1763003832995, onlineFirstDateStr=2025-11-13, sourceXml=null, magXml=null, createTime=1763003832995, creator=13701087609, updateTime=1763003832995, updator=13701087609, issue=Issue{id=1195707415279747621, tenantId=1146029695717560320, journalId=1190317699101192196, year='2024', volume='59', issue='3', pageStart='193', pageEnd='284', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1763008462972, creator=13701087609, updateTime=1763009150406, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1195710298666611616, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1195707415279747621, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1195710298670805921, tenantId=1146029695717560320, journalId=1190317699101192196, issueId=1195707415279747621, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=263, endPage=269, ext={EN=ArticleExt(id=1195687995979383700, articleId=1195687995748696977, tenantId=1146029695717560320, journalId=1190317699101192196, language=EN, title=Synthesis, Characterization and Physicochemical Properties of an Famotidine and P-toluenesulfonic Acid Cocrystal, columnId=null, journalTitle=Chinese Pharmaceutical Journal, columnName=null, runingTitle=null, highlight=null, articleAbstract=

OBJECTIVE To synthesize p-toluenesulfonic acid(PTS) and famotidine(FMT) cocrystal in order to improve thesolubility of famotidine in water and the permeability. OBJECTIVE The cocrystal was prepared by solvent evaporation method combined with ultrasound. The cocrystal was characterized by scanning electron microscopy, differential scanning calorimetry, thermogravimetric analysis, infrared spectroscopy and powder X-ray diffraction. The single crystal structure of FMT-PTS-H2O(1∶1∶1) was successfully obtained, and the solubility and permeability of the newly synthesized cocrystal were studied. RESULTS After the formation of cocrystal, the water solubility and permeability of FMT increased by 1.54 and 2.29 times, respectively. CONCLUSION Compared with FMT, the solubility and permeability of FMT after the formation of cocrystal were improved. This study provides a method for improving the permeability of biopharmaceutics classification system(BCS)Ⅲ drugs, which will contribute to the development of low permeability drugs.

, correspAuthors=YANG Zhao, authorNote=null, correspAuthorsNote=null, copyrightStatement=null, copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=null, magXml=null, pdfUrl=null, pdf=null, pdfFileSize=null, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=null, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=null, mapNumber=null, authorCompany=null, fund=null, authors=null, authorsList=ZHAO Yongfeng, FAN Ying, ZHANG Yan, XU Hong, LI Min, YANG Zhao), CN=ArticleExt(id=1195688751998484907, articleId=1195687995748696977, tenantId=1146029695717560320, journalId=1190317699101192196, language=CN, title=法莫替丁-对甲苯磺酸共晶的制备表征及性质研究, columnId=1190352405612040510, journalTitle=中国药学杂志, columnName=论著, runingTitle=null, highlight=null, articleAbstract=

目的 为了提高法莫替丁在水中的溶解度及其渗透性,采用药物共结晶技术,以对甲苯磺酸(PTS)和法莫替丁(FMT)为原料合成了药物共晶。方法 利用结合超声的溶剂挥发法制备共晶,通过扫描电镜、差示扫描量热法、热重分析、红外光谱和粉末x射线衍射对共晶进行了表征。应用X射线单晶衍成功获得了FMT-PTS-H2O(1∶1∶1)的单晶结构,对新合成的共晶的溶解度和渗透性进行了研究。结果 形成共晶后,FMT的水溶性和渗透性分别提高了1.54和2.29倍。结论 与FMT原料药相比,形成共晶后的FMT溶解度和渗透性都有所提高。本研究为提高生物药剂学分类系统(BCS)Ⅲ类药物的渗透性提供了一种方法,将有助于低渗透性药物的开发。

, correspAuthors=杨钊, authorNote=null, correspAuthorsNote=
*杨钊,男,博士,主任药师 研究方向:药物分析 Tel:(0532)58759188
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赵永凤,女,硕士研究生 研究方向:药物分析

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赵永凤,女,硕士研究生 研究方向:药物分析

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赵永凤,女,硕士研究生 研究方向:药物分析

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DOI:10.1016/j.ijpharm.2021.121116., articleTitle=Towards a better mechanistic comprehension of drug permeation and absorption: introducing the diffusion-partitioning interplay, refAbstract=null), Reference(id=1197102032705335325, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1195687995748696977, doi=null, pmid=null, pmcid=null, year=2019, volume=19, issue=10, pageStart=5636, pageEnd=5647, url=null, language=null, rfNumber=[32], rfOrder=31, authorNames=TAO, HAO Q Q, VORONIN A P, journalName=Cryst Growth Des, refType=null, unstructuredReference=TAO, HAO Q Q, VORONIN A P, et al. Polymorphic forms of a molecular salt of phenazopyridine with 3,5-Dihydroxybenzoic acid: crystal structures, theoretical calculations, thermodynamic stability and solubility aspects[J]. 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journalId=1190317699101192196, articleId=1195687995748696977, language=CN, label=图11, caption=FMT 和 FMT-PTS-H2O 8 h渗透总量, figureFileSmall=iL1ZhgZFk2ijQN1N1cNs+w==, figureFileBig=oOMKEsUX+pAve/0PPdQxhA==, tableContent=null), ArticleFig(id=1197102030205531131, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1195687995748696977, language=EN, label=Tab.1, caption=

Crystallographic parameters of FMT-PTS-H2O cocrystal

, figureFileSmall=null, figureFileBig=null, tableContent=
Empirical formula C15H25N7O6S4
Formula weight 527.66
Temperature(K) 150(2)
Wavelength(°), Mo-Kα 0.710 73
Crystal system Monoclinic
Space group P2(1)/n
a/Å 7.078 7(4)
b/Å 26.527 5(15)
c/Å 12.600 4(6)
α/° 90
β/° 104.817(2)
γ/° 90
Volume/Å3 2 287.4(2)
Z 4
F(000) 1 104
Crystal size/mm 0.120,0.110,0.100
θ range for data collection/° 2.270-26.347
Limiting indices -8≤h≤8, -33≤k≤33, -15≤l≤15
Tot., uniq. data, r(int) 31 538,4 667,0.060 3
Observed data [I>2σ(I)] 4 169
R1,ωR2, S 0.081 1,0.165 7,1.218
Deposition number 2 178 907
), ArticleFig(id=1197102030281028604, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1195687995748696977, language=CN, label=表1, caption=

FMT-PTS-H2O的晶体学参数

, figureFileSmall=null, figureFileBig=null, tableContent=
Empirical formula C15H25N7O6S4
Formula weight 527.66
Temperature(K) 150(2)
Wavelength(°), Mo-Kα 0.710 73
Crystal system Monoclinic
Space group P2(1)/n
a/Å 7.078 7(4)
b/Å 26.527 5(15)
c/Å 12.600 4(6)
α/° 90
β/° 104.817(2)
γ/° 90
Volume/Å3 2 287.4(2)
Z 4
F(000) 1 104
Crystal size/mm 0.120,0.110,0.100
θ range for data collection/° 2.270-26.347
Limiting indices -8≤h≤8, -33≤k≤33, -15≤l≤15
Tot., uniq. data, r(int) 31 538,4 667,0.060 3
Observed data [I>2σ(I)] 4 169
R1,ωR2, S 0.081 1,0.165 7,1.218
Deposition number 2 178 907
), ArticleFig(id=1197102030335554557, tenantId=1146029695717560320, journalId=1190317699101192196, articleId=1195687995748696977, language=EN, label=Tab.2, caption=

Hydrogen-bonding geometries of FMT-PTS-H2O. Å,°

, figureFileSmall=null, figureFileBig=null, tableContent=
D H…A d(D H) d(H…A) ∠D H…A
N1 H1A…O5 0.87 2.21 174.0
N3 H3A…O1 0.88 2.29 123.4
N5 H5…O6 0.88 1.87 162.3
N6 H6B…O6 0.88 2.29 140.7
N7 H7B…N4 0.88 2.07 130.7
N7 H7A…O3 0.88 2.36 129.0
O6 H6D…O4 0.87 1.90 175.1
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FMT-PTS-H2O的重要氢键. Å,°

, figureFileSmall=null, figureFileBig=null, tableContent=
D H…A d(D H) d(H…A) ∠D H…A
N1 H1A…O5 0.87 2.21 174.0
N3 H3A…O1 0.88 2.29 123.4
N5 H5…O6 0.88 1.87 162.3
N6 H6B…O6 0.88 2.29 140.7
N7 H7B…N4 0.88 2.07 130.7
N7 H7A…O3 0.88 2.36 129.0
O6 H6D…O4 0.87 1.90 175.1
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法莫替丁-对甲苯磺酸共晶的制备表征及性质研究
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赵永凤 1 , 范莹 2 , 张燕 3 , 徐红 4 , 李敏 5 , 杨钊 1, 3, *
中国药学杂志 | 论著 2024,59(3): 263-269
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中国药学杂志 | 论著 2024, 59(3): 263-269
法莫替丁-对甲苯磺酸共晶的制备表征及性质研究
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赵永凤1, 范莹2, 张燕3, 徐红4, 李敏5, 杨钊1, 3, *
作者信息
  • 1 青岛大学药学院, 山东 青岛 266071
  • 2 海军青岛特勤疗养中心药剂科, 山东 青岛 266071
  • 3 青岛食品药品检验研究院, 山东 青岛 266071
  • 4 山东科技大学, 山东 青岛 266590
  • 5 安丘市人民医院, 山东 潍坊 262199

    • 赵永凤,女,硕士研究生 研究方向:药物分析

通讯作者:

*杨钊,男,博士,主任药师 研究方向:药物分析 Tel:(0532)58759188
Synthesis, Characterization and Physicochemical Properties of an Famotidine and P-toluenesulfonic Acid Cocrystal
ZHAO Yongfeng1, FAN Ying2, ZHANG Yan3, XU Hong4, LI Min5, YANG Zhao1, 3, *
Affiliations
  • 1 College of Pharmacy, Qingdao University, Qingdao 266071, China
  • 2 Pharmacy Department, Qingdao Special Servicemen Recuperation Center of CPLA Navy, Qingdao 266071, China
  • 3 Qingdao Institute for Food and Drug Control, Qingdao 266071, China
  • 4 Shandong University of Science and Technology, Qingdao 266590, China
  • 5 Anqiu People's Hospital,Weifang, 262199, China
出版时间: 2024-02-08 doi: 10.11669/cpj.2024.03.010
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摘要
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目的 为了提高法莫替丁在水中的溶解度及其渗透性,采用药物共结晶技术,以对甲苯磺酸(PTS)和法莫替丁(FMT)为原料合成了药物共晶。方法 利用结合超声的溶剂挥发法制备共晶,通过扫描电镜、差示扫描量热法、热重分析、红外光谱和粉末x射线衍射对共晶进行了表征。应用X射线单晶衍成功获得了FMT-PTS-H2O(1∶1∶1)的单晶结构,对新合成的共晶的溶解度和渗透性进行了研究。结果 形成共晶后,FMT的水溶性和渗透性分别提高了1.54和2.29倍。结论 与FMT原料药相比,形成共晶后的FMT溶解度和渗透性都有所提高。本研究为提高生物药剂学分类系统(BCS)Ⅲ类药物的渗透性提供了一种方法,将有助于低渗透性药物的开发。

法莫替丁  /  对甲苯磺酸  /  晶体结构  /  水溶性  /  渗透性

OBJECTIVE To synthesize p-toluenesulfonic acid(PTS) and famotidine(FMT) cocrystal in order to improve thesolubility of famotidine in water and the permeability. OBJECTIVE The cocrystal was prepared by solvent evaporation method combined with ultrasound. The cocrystal was characterized by scanning electron microscopy, differential scanning calorimetry, thermogravimetric analysis, infrared spectroscopy and powder X-ray diffraction. The single crystal structure of FMT-PTS-H2O(1∶1∶1) was successfully obtained, and the solubility and permeability of the newly synthesized cocrystal were studied. RESULTS After the formation of cocrystal, the water solubility and permeability of FMT increased by 1.54 and 2.29 times, respectively. CONCLUSION Compared with FMT, the solubility and permeability of FMT after the formation of cocrystal were improved. This study provides a method for improving the permeability of biopharmaceutics classification system(BCS)Ⅲ drugs, which will contribute to the development of low permeability drugs.

famotidine  /  p-toluenesulfonic  /  crystal structure  /  aqueous solubility  /  permeability
赵永凤, 范莹, 张燕, 徐红, 李敏, 杨钊. 法莫替丁-对甲苯磺酸共晶的制备表征及性质研究. 中国药学杂志, 2024 , 59 (3) : 263 -269 . DOI: 10.11669/cpj.2024.03.010
ZHAO Yongfeng, FAN Ying, ZHANG Yan, XU Hong, LI Min, YANG Zhao. Synthesis, Characterization and Physicochemical Properties of an Famotidine and P-toluenesulfonic Acid Cocrystal[J]. Chinese Pharmaceutical Journal, 2024 , 59 (3) : 263 -269 . DOI: 10.11669/cpj.2024.03.010
正文
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临床上,许多固体形式的活性药物成分(API),由于其溶解度低或渗透性差而导致生物利用度较低[1]。合成盐、溶剂化物或共晶形式为解决原料药的溶解度[2]、渗透性[3]和生物利用度[4]问题提供了思路。盐和共晶的定义有部分重叠,可以称之为盐共晶或离子共晶[5]。共晶形成过程中没有共价键的形成,因此共晶在不改变原料药分子结构的前提下,可以改善原料药的某些性质缺陷,如稳定性[6]、湿度[7]、溶解度[8]、溶出率[9]和生物利用度[10-11]。与原料药共结晶的其他生物学可接受分子叫作配体(CCF)。晶体工程首次提出于1955年,并由Schmidt于1971年应用[12]。 Etter[13]和Desiraju[14]后来识别、表征并利用超分子相互作用生成新的固体形式。通过发现药物的超分子合成子[15-16]来合理选择所需API的CCF。
法莫替丁(FMT)是一种富电子结构,更容易与酸性CCF形成共晶。FMT的胍基是最好的氢键供体之一(图1A);对甲苯磺酸(PTS)含有一个磺酸基磺酸基是与FMT形成异质超分子合成子的潜在位点(图1B)。FMT是一种组胺H2受体拮抗剂,具有抑制胃酸分泌的作用[17]。主要用于治疗胃十二指肠溃疡、反流性食管炎、上消化道出血等疾病。PTS是一种非氧化性有机酸,白色针状或粉状晶体,可溶于水、醇、醚等极性溶剂。目前,由PTS与依度沙班形成的共结晶产品依度沙班PTS一水合物(Savaysa)已获得美国食品药品管理局(FDA)[18]的批准上市,并用于预防重大骨科手术后静脉血栓栓塞(VTE)。根据生物药剂学分类系统(BCS), FMT属于BCSⅢ类药物[19],渗透性较差,口服吸收和生物利用度受到严重影响。药物共结晶技术可以在不改变原料药化学结构和内在生物活性的前提下,优化原料药的理化性质和药代动力学性质。
1 材料与方法
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1.1 材料
FMT(原料药,晶型B,青岛立腾化学医学研究有限公司);PTS[阿拉丁(上海)公司]。乙腈为色谱纯;纯度99.5%醋酸钠;99.0%冰乙酸;99.0%磷酸二氢钠;96%氢氧化钠。
1.2 方法
1.2.1 共晶培养
采用结合超声的溶剂蒸发法进行培养。FMT先用乙腈溶解超声1 h,待FMT溶解后,加入PTS,超声持续0.5 h。将得到的溶液冷却至室温,过滤后密封扎孔,在室温下缓慢蒸发。经过1~2 d,得到适合单晶X射线衍射的无色细针状晶体。
1.2.2 扫描电子显微镜(SEM)
将样品固定在黏有双面胶的铝板上,并涂上铂层使其导电。在20.0 kV真空扫描电镜下,采用扫描电子显微镜(VEGA3,捷克)分析FMT,PTS以及共晶的晶体形态。
1.2.3 差示扫描量热(DSC)
使用DSC 6000(美国Perkin Elmer公司)进行DSC分析,3~5 mg样品进行实验,氮气流速为20 mL·min-1,升温速率为20 ℃·min-1,温度范围为30~250 ℃。
1.2.4 热重分析(TGA)
使用TGA 4000(美国Perkin Elmer公司)进行热重分析,5~12 mg样品进行实验,氮气流速为20 mL·min-1,升温速率为20 ℃·min-1,温度范围为30~350 ℃。
1.2.5 X射线粉末衍射(PXRD)
使用D8 Focus(德国Bruker公司)进行PXRD分析,样品放在一个有凹槽的小圆盘中压平。使用Cu-kα(1.540 60 Å),电压和电流分别设为40 kV和40 mA。数据采集在室温下,反射模式范围为10~40°,扫描速度为2°·min-1。
1.2.6 X射线单晶衍射(SXRD)
采用Bruker APEX-Ⅱ CCD衍射仪采集单晶x射线衍射数据。Mo-Kα(0.710 73 Å),在150(2)K, 4.6°<2θ<50°条件下检测,在ω/2θ扫描模式下收集发射数据。
1.2.7 傅里叶红外光谱(FT-IR)
采用Thermo Nicolet IS5 FT-IR光谱仪进行。将2 mg样品与20 mg干燥KBr混合,充分研磨,然后压片,扣除KBr背景采集样品红外光谱。
1.2.8 高效液相色谱检测条件
采用Agilent 1260高效液相色谱分析仪,CAPCELL PAK MG-ⅡC18色谱柱(4.6 mm×250 mm,5 μm)。流动相为13.6 mg·mL-1醋酸缓冲液-乙腈(93∶7)。流速为1.5 mL·min-1,检测波长为270 nm。柱温35 ℃。进样量为20 μL。精密称取法莫替丁对照品0.050 16 g,置于50 mL量瓶中,配置一系列质量浓度为1.00、5.02、10.03、50.16、100.32 μg·mL-1的标准溶液。
1.2.9 平衡溶解度
用摇瓶法测定FMT-PTS-H2O共晶与原料药的平衡溶解度。将过量的FMT和FMT-PTS-H2O分别置于装有20 mL水的带塞锥形瓶中,置于25 ℃恒温摇床(IKA KS 4000i)中。分别于4、6 h取适量样品。过滤后,用磷酸盐缓冲溶液稀释至适当浓度。采用高效液相色谱法计算FMT和FMT-PTS-H2O的平衡溶解度。每个样品在相同条件下平行测试2次,实验结束后取剩余共晶样品干燥后进行粉末衍射测定。
1.2.10 渗透性
采用德国LOGAN公司生产的渗透板(Permeapad 96孔渗透板)测量FMT-PTS-H2O共晶及其原料药的渗透性。渗透板底层为接收室放入pH 7.4的磷酸盐缓冲液400 μL;中层为渗透膜层(0.20 cm2),加入过量粉末样品后加入50 μL水。最上层用密封膜覆盖密封。置于37 ℃ 200 rpm的恒温摇床上,每小时取出全部接受液,同时加入等量新鲜接受液。实验结束后,采用上述液相法进行测定,在相同条件下进行2次测量,并计算平均值。
2 结果与讨论
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2.1 扫描电镜结果
放大500倍的扫描电子显微镜图像见图2。从图2中可以看出,FMT的粒径大小不均匀,外观呈棱柱状(图2A);PTS表面粗糙,外观呈稀疏的块状(图2B);FMT-PTS-H2O外观呈细小的针状,表面光滑致密(图2C)。上述结果表明,共晶的形态与API和CCF均不同,预示着共晶的物理化学性质可能发生变化。
2.2 DSC结果
DSC是确定新晶相形成的第一步,新形成的共晶具有与API和CCF均不同的吸热行为[20]。FMT、PTS、FMT-PTS-H2O共晶和物理混合物(API-CCF=1∶1)的DSC图谱见图3,产物DSC图谱在127.00 ℃ 显示出1个独立的吸热峰,该吸热峰介于FMT(171.70 ℃)和PTS(109.45 ℃)之间。这表明该产物既不是单一成分,也不是简单的物理混合物,而是一种具有独特熔点的新物质,提示可能形成了共晶。
2.3 TGA结果
TGA作为表征晶体的一种手段,与DSC共同研究了产物的热行为[21]。不仅可以判断产物的热稳定性,还能初步确定产品是否含有溶剂,特别是水分子。蓝色曲线显示了FMT-PTS-H2O共晶的TGA热力学变化(图4),其中包括失重的2个阶段。第一阶段小的失重峰在100 ℃左右,说明该结构可能含有水分子。图中116 ℃时3.36%的微小失重可能对应于结构中水分子的蒸发,这与下面的单晶结构结果一致,即FMT-PTS-H2O共晶中含有1个水分子,水分子的理论计算值为3.41%。第二阶段为FMT-PTS-H2O共晶熔点后的212 ℃左右,降解过程发生在产物熔点之后,说明产物热稳定性良好。
2.4 PXRD结果
PXRD作为一种成熟的晶体表征方法,被广泛应用于晶体材料的结构表征[22]。作为一种重要的晶体表征技术,它能提供有关结晶、纯度和结晶程度的重要信息。对FMT-PTS-H2O共晶和原料FMT、PTS进行PXRD测试,并对其衍射图样进行了记录和描述(图5)。新合成的FMT-PTS-H2O共晶分别在2θ为13.34°、14.46°、21.14°、22.18°、25.67°和30.65°等多处出现了新的衍射峰。这些特征峰是新生成的,在FMT和PTS衍射图中不存在。且FMT-PTS-H2O共晶的衍射图中FMT在11.69°、24.21°、35.44°的特征衍射峰和PST在19.34°、25.29°的特征衍射峰消失,证实了新晶相的形成,与上述DSC、TGA分析结果一致。此外,从图5中还可以看出,实验所测PXRD图谱与单晶模拟获得的FMT-PTS-H2O共晶PXRD图谱一致,说明制备的样品具有较高的纯度。
2.5 单晶结构
X射线结构分析表明,该晶体属于P2(1)/n空间群的单斜体系。晶胞参数及相关的晶体学参数见表1。FMT-PTS-H2O共晶的不对称单元由1个FMT、1个PTS和1个H2O组成(图6)。在FMT-PTS-H2O分子单元中存在2种分子间氢键。FMT中胍基上的N5-H5与水分子上的氧原子形成氢键N5-H5…O6;PTS中磺酸基上的O4与水分子上的氢原子形成氢键O6-H6D…O4。水分子作为连接FMT和PTS的唯一桥梁,在结构中起着重要作用。连接扩展了堆叠,形成了超分子的堆叠网络结构(图7)。Sander等[23]报道说,插入的溶剂分子也可以导致共晶组分之间完全缺乏直接相互作用。在本文中,FMT与PTS不是直接连接,而是以水分子为桥梁形成共晶。剑桥结构数据库的一项调查表明,由于插入的水分子,组分之间缺乏直接的氢键是罕见的。该晶体的晶体学信息文件(CIF)已上传至剑桥晶体数据库中心,收藏号为2178907。FMT-PTS-H2O共晶结构中的水分子来源于空气,在较高的湿度下晶体生长较好。从晶体结构可以看出,晶体中发生了质子转移,氢键的键长在1.9~2.9之间[24-25](表2),属于氢键的范围,属于共晶的定义范围。
2.6 傅里叶变换红外光谱
在4 000~400 cm-1[26]范围内采集了API、CCF和共晶的红外光谱,初步揭示了API和CCF在共晶形成过程中不同吸收峰的波数变化,并验证了x射线单晶衍射形成的氢键位点。记录的FMT-PTS-H2O共晶和FMT、PTS的红外吸收光谱见图8。FMT在1 640 cm-1处的吸收峰对应胍的C=N伸缩振动。形成FMT-PTS-H2O共晶后,1 640 cm-1处的最大吸收峰移至1 659 cm-1处。同时,PTS在1 111 cm-1处的最大吸收峰是磺酸基团的伸缩振动引起的。FMT-PTS-H2O共晶形成后,1 111 cm-1处的最大吸收峰移至1 103 cm-1处。一系列红外波峰从1 640到1 659 cm-1,从1 111到1 103 cm-1。这些变化是由于FMT, PTS之间氢键的形成。
2.7 平衡溶解度
HPLC测定的FMT在4 和6 h时样品浓度基本一致,说明FMT在4 h时在原料药和共晶中已达到平衡,溶解度不再增加。25 ℃时FMT原料药在水中的平衡溶解度为0.77 mg·mL-1;FMT-PTS-H2O的平衡溶解度为1.19 mg·mL-1。综上所述,与PTS形成盐共晶后,FMT的溶解度提高到了原来的1.54倍。采集剩余的FMT-PTS-H2O共晶实验样品,PXRD测试与实验前相同,说明实验结束后样品未发生明显变化(图9)。
从结构的角度来看,共晶溶解度的增加可以解释为当暴露在水环境中时,晶体中溶解度较高的水分子和PTS分子首先溶解在水中,然后整个晶体中只有FMT分子以非晶态漂浮在水溶液中。这种非晶态在水溶液中迅速消散并溶于水,形成共晶后的FMT溶解度高于API分子[27]。综上所述,FMT水溶性的提高主要得益于PTS的高水溶性。
2.8 渗透性
体外渗透性测量通常采用大鼠肠灌注、仿生渗透膜和Caco-2细胞实验[28-29]。本次渗透性研究使用的是基于磷脂的层状结构的人工仿生膜Permeapad®[30]。Permeapad®与Caco-2测量数据有良好的相关性。在本研究中,实验共进行8 h,每小时测量一次药物在膜上的渗透性[31],得到FMT和FMT-PTS-H2O共晶的每小时通透率和8 h通透总量。FMT和FMT-PTS-H2O共晶的每小时渗透率和渗透总量见图10~11。从图10可以看出,FMT-PTS-H2O比FMT的每小时渗透率高。从图11可以看出,FMT-PTS-H2O比FMT在8 h后的累计渗透总量要也要高。8 h后FMT-PTS-H2O的总渗透率约为FMT的2.29倍。形成共晶后增强了FMT对人工膜的穿透能力。
这可以通过以下原因来解释:一方面,盐共晶优异的溶解度导致膜上有较大的浓度梯度,可作为提高膜通透性的驱动力;另一方面,渗透率的增加也可能是由于PTS比FMT具有更好的亲脂性[32]。脂水分布系数(logP)作为评价共晶渗透率的重要参数,对共晶渗透性具有重要的参考价值。与FMT相比,PTS的logP值更高(1.7 vs. -0.4)。共晶体利用PTS的渗透性优势,提高了FMT的渗透性。
3 结论
收起
为了改善FMT的渗透性及水溶性,采用药物共结晶技术合成了FMT-PTS-H2O共晶,并通过DSC、TGA、SEM、FT-IR、PXRD等多种手段对其进行表征。通过SXRD成功地获得了单晶结构。体外性质研究表明,FMT的水溶性和渗透性分别提高了1.54和2.29倍。由于PTS的水溶性以及logP值高于FMT,所以提高了FMT的水溶性及渗透性。获得的FMT-PTS-H2O共晶有望提高FMT的生物利用度,还需要进一步的实验来证实。本研究提供了一种提高BCS Ⅲ类药物通透性的合成方法,有助于低通透性药物的开发。
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doi: 10.11669/cpj.2024.03.010
  • 接收时间：2023-06-12
  • 首发时间：2025-11-13
  • 出版时间：2024-02-08
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  • 收稿日期：2023-06-12
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    1 青岛大学药学院, 山东 青岛 266071
    2 海军青岛特勤疗养中心药剂科, 山东 青岛 266071
    3 青岛食品药品检验研究院, 山东 青岛 266071
    4 山东科技大学, 山东 青岛 266590
    5 安丘市人民医院, 山东 潍坊 262199

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*杨钊,男,博士,主任药师 研究方向:药物分析 Tel:(0532)58759188
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2种不同金属材料的力学参数
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Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
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鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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